Cape Cod Guide on LEO edit.
City Guides

The Complete Guide to Cape Cod

As far back as I can remember, I had been looking to find the place I would one day want to spend my summers. A place to come back to year after year. Where my kids could grow up in the summers. I, myself, grew up in the beach towns of Italy, France, and Spain yet always dreamt of the small American seaside towns I had seen in movies—with their Main Streets and cottages, bike trails, and drive-in movie theaters. A local’s paradise. A place that felt untouched by time. I looked for many years for such a place. And then I found Cape Cod.

The Cape is the hook-shaped peninsula, often referred to as an upheld crooked “arm”, that sticks out from Massachusetts and extends east into the Atlantic Ocean, where the beauty of its revered National Seashore is iconic. There are more than a dozen towns that make up Cape Cod, organized into four regions: the Upper Cape, Mid Cape, Lower Cape, and Outer Cape, although you will soon find these titles to be almost certainly designed to confuse you. Don’t worry, we break it down for you below.

WEATHER

Typically, Cape Cod sees its warmest month of the year in July, with the average highest temperature reaching 78° and a low of 63°. August sees an average high of 77°, and the low average of 63° carrying over from July. End of spring and early fall usher in the easiest temperatures.

BEST TIME TO VISIT

The shoulder months offer fewer crowds than the busy summer season, with better prices on accommodations; this is when you would go to decompress and get the place all to yourself. December through March are near abandoned, with a lot of shops and restaurants closed for the offseason. July and August attract the most tourism, although it somehow manages to maintain an authentic, locals feel. Avoid weekend traffic at all costs.

HOW TO GET HERE

Just over an hour out of Boston, without traffic. And Cape Cod is famous for its weekend traffic, so if you’re driving, try to avoid coming in on a Friday or the first half of Saturday, and avoid leaving on a Sunday, or even Monday morning.

The most fun way to get there is the fast ferry from Boston into Provincetown. You can take a Fast Ferry in 90-minutes across the bay. Once you arrive, you’ll need to rent a car to to really get around. There is a public bus system, but it won’t get you everywhere.

LAY OF THE LAND

Cape Cod is 70 miles long with the peninsula tapering to a hook at its outermost point, with Cape Cod Bay on the west and south and the Atlantic Ocean on east and north. On the Oceanside, you have your iconic Cape Cod National Seashore—epically beautiful with better waves and known for its many shark warnings. On the Bayside, you get flatter, calmer waters and Kettle Ponds—great for kids, paddle boarding and kayaking—as well as the harbor. The cape boasts 14 lighthouses, which are a rite of passage and have been an excuse for many a road trip. Whale watching is a must and will change the way you think about life on Earth.

To generalize, Upper and Mid Cape get more of the weekend crowds coming in from the city, while folks coming on vacation for longer stays and from further away, looking for that classic Cape Cod experience, will travel farther out and get situated in Lower or Outer Cape.

Keep well in mind that all the towns on the side of the coast you chose are close to each other, so wherever you set up base, you can easily drive over to one of the other nearby towns for a dinner or a preferred beach, drive-in theater or a longer day trip. So be sure to take a good dive into the full guide for a myriad of options no matter where you’re staying.

cape cod map on LEO edit.
Illustration by John S. Dykes

Guide Tip: click on the town names in bold below to skip right to their guides.

UPPER CAPE
Upper Cape includes Sandwich, Bourne, Falmouth, and Mashpee. These are going to be closest to the city and to Sagamore Bridge, which takes you from Boston and drops you right into Bourne. Falmouth is a favorite of the Upper Cape, and is the gateway to Martha’s Vineyard and Nantucket. The name is misleading as Falmouth is actually on the lowest part of the Cape.

MID CAPE
Meantime, Mid Cape is comprised of the towns that are actually at the top—Barnstable, Dennis, and Yarmouth, with the exception of Hyannis and affluent Osterville. Hyannis is the biggest metropolis on the cape and where you would go in search of a mall. Dennis is beautiful, more residential. A friend once told me that Barnstable is where you might go run more serious errands (indeed, there is a courthouse there).

LOWER CAPE
The “elbow” of the Cape, it lies on the southeastern part of the cape and constitutes of quaint Harwich, charming Brewster, shoppable Orleans, and tourist-friendly Chatham. Lower Cape gives you a ton of access to its surrounding towns and Outer Cape, so it makes for a great base.

OUTER CAPE
The “arm” of the cape, culminating in the highest point, most eastern point—Provincetown, sometimes referred to as “the fist.” Outer Cape consists of lively Provincetown and nearby, more secluded, naturally-friendly Truro, classically New England Wellfleet and Eastham. As it’s also the narrowest part of the Cape, each town has the benefit of having easy access to both the ocean side and the bay side.

HOUSE RENTALS

Besides staying in one of its many B&Bs, inns, or hotels, many visitors (myself included) choose to rent a house. An easier choice if you come with a large group (or young kids), or for a longer stay. When it comes to the Cape, I had better luck finding rental properties with local companies than with the usual suspects of Air Bnb or VRBO. One of them being Robert Paul Properties, which has rentals for the entire cape. More town-specific rentals will be listed below. When renting a house with kids, I always use Baby Quip to rent anything from strollers to cribs and even toys.

CHATHAM

Chatham is a great base as it’s charming, with stunning beaches and plenty of activities, a bustling Main Street, great restaurants, and easy access to its surrounding towns. Harwich is a stone’s throw away, going into Wellfleet for its Kettle Ponds or for a night at the drive-in is no biggie, and taking a day trip up the cape to Provincetown (with gorgeous Truro on the way) won’t take you longer than hour if you’re smart about traffic hours. It’s also got the most tourists on the Cape, which turns off some of the snobbier locals.

WHERE TO STAY

CHATHAM BARS INN

The first-ever luxury hotel on Cape Cod and one of the most beautiful and popular on the Cape (and a hit with the wedding crowd). Has a renovated spa, four restaurants, and pool.

chatham bars inn on LEO edit.
Photo Courtesy of Chatham Bars Inn

297 Shore Rd / Chatham / 508.945.0096

CHATHAM INN

A luxurious boutique hotel that blends the soul of the historic inn with modern decor and amenities, with a fine dining restaurant and popular wine bar.

chatham inn on LEO edit.
Photo Courtesy of Chatham Inn

359 Main St / Chatham / 508.945.9232

CHATHAM VACATION RENTALS

I ended up renting our last house from Chatham Vacation Rentals and would do so again and again. Even very late in the game, they had an overwhelming amount of great options, were incredibly personable and accommodating, and always responded to my emails or calls right away.

WHERE TO EAT

THE IMPUDENT OYSTER

Get a reservation ASAP for an amazing dinner. Best food in Chatham. Not really for the kids.

the impudent oyster on LEO edit.
Photo Courtesy of Impudent Oyster

15 Chatham Bars Ave / Chatham / 508.945.3545

THE CHATHAM SQUIRE

Best place for chowder and a Sam Adams. Very kid-friendly.

the chatham squire on LEO edit.
Photo Courtesy of the Chatham Squire

Main St / Chatham / 508.945.0945

CHATHAM PIER FISH MARKET

Right in the center of town. Best lobster roll, BYOB, sit at the picnic tables and watch the boats bring in the day’s haul and see the seals swimming. Super casual, and it’s been there forever.

chatham pier fish market on LEO edit.
Photo Courtesy of Chatham Pier Fish Market

45 Barcliff Ave / Chatham / 508.945.3474

SNOWY OWL ROASTERS

This quaint little hidden grab and go spot is one of the few in the area with a pretty full coffee bar (it’s that or Dunkin’s pretty much). Espressos, lattes, brewed coffees and more.

Photo Courtesy of Snowy Owl

2624 Main St / Brewster, MA 02631 / 774.323.0605

FILLING STATION

Good for breakfast and kid friendly.

filling station on LEO edit.
Photo Courtesy of Filling Station

75 Old Harbor Rd / Chatham / 508.945.4380

PISCES

Great for an adult night out. Sandwiched right between Chatham and Harwich.

pisces cape code on LEO edit.
Photo Courtesy of Pisces

2653 Main St / South Chatham / 508.432.4600

CHATHAM WINE BAR

A great little inn for drinks with a good wine bar, and you can walk around Main Street.

chatham wine bar on LEO edit.
Photo Courtesy of Chatham Wine Bar

359 Main St #2 / Chatham / 508.945.1468

CHATHAM BARS INN

Brunch, lunch, dinner or anything here. It’s one of the most beautiful hotels on Cape Cod, and the clambakes outdoors include s’mores on the beach and movies by the pool.

chatham bars inn on LEO edit.
Photo Courtesy of Chatham Bars Inn

297 Shore Rd / Chatham / 508.945.0096

LARRY’S PX

A popular divey diner for breakfast.

larry's px on LEO edit.

1591 Main St / Chatham / 508.945.3964

THE RED NUN

Local fisherman spot to eat the best clam chowder.

the red nun on LEO edit.
Photo Courtesy of The Red Nun

746 Main St / Chatham / 508.348.0469

BLUEFIN SUSHI

Everyone loves this spot for sushi.

bluefin sushi on LEO edit.
Photo Courtesy of Bluefin Sushi

513 Main St / Chatham / 508.348.1573

CHATHAM COOKWARE CAFE

This cute little spot sells everything except cookware. Great for breakfast, sandwiches, and ice cream.

chatham cookware cafe on LEO edit.
Photo Courtesy of Chatham Cookware Cafe

524 Main St / Chatham / 508.945.1250

MARION’S PIE SHOP

Honest to goodness, the best damn pie I may have ever had. Get them to go and heat them up at home. I say ‘them’ because you’ll want to get at least one savory and one sweet. It’s right across from awesome Ridgevale Beach.

marions pie shop on LEO edit.
Photo Courtesy of Marion’s Pie Shop

2022 Main St / Chatham / 508.432.9439

DEL MAR

Modern bistro cuisine. Wood-fired thin crust pizza, good pasta, serious steaks, and a lively bar scene.

del mar on LEO edit.
Photo Courtesy of Del Mar

907 Main St / Chatham / 508.945.9988

PATES

One of the more foodie-friendly spots in Chatham (and more expensive too), serving hand-cut steaks, fresh oysters, and unique dishes like miso rubbed chicken salad and Korean broccoli. The bar serves great cocktails.

pates on LEO edit.
Photo Courtesy of Pates

1260 Main St / Chatham / 508.945.9777

HANGAR B

It’s at the tiny Chatham airport, so you can eat delicious breakfast while watching planes take off.

hangar b on LEO edit.
Photo Courtesy of Hangar B

240 George Ryder Rd / Chatham / 508.593.3655

SWEET TOMATO PIZZA

It’s just a little hole in the wall on the side of the main strip on the way to Main Street, but it’s some of the best pizza this Italian’s ever had.

sweet tomato pizza on LEO edit.
Photo Courtesy of Sweet Tomato Pizza

790 Main St / Chatham / 508.348.0200

CHATHAM CANDY MANOR

The best fudge in Chatham, and of course they serve ice cream too (you can’t throw a coin on the cape without hitting an ice cream spot).

chatham candy manor on LEO edit.
Photo Courtesy of Chatham Candy Manor

 484 Main St / Chatham / 508.945.0825

BUFFY’S ICE CREAM

Great spot with the kids as you can take a seat at one of the picnic tables outside. Ice cream is delicious and they even have sundaes.

Photo Courtesy of Buffy’s Ice Cream

456 Main St / Chatham, MA 02633 / 508.945.5990

BRICK BLOCK ICE CREAM & CREPES

Great for a late night post dinner spot as they’re open till 11pm every night. The crepes sell out fast on busy nights and the ice cream is homemade.

Photo Courtesy of Brick Block Ice Cream & Crepes

10 Chatham Bars Ave, Chatham, MA 02633 / 774.836.7217

BEACHES

A few favorites in town: Oyster Pond, a kid friendly beach that’s mellow, with warm water and lots of little ones running around. Ridgevale beach, pretty busy and parking will cost you, but it has a classic little shack selling snacks & ice cream (family-owned and operated for 60 years!) and even the very youngest kids will love playing in the shallow tidal pools. Lighthouse beach, picturesque and huge with sweeping dunes and grass like out of a Norman Rockwell Cape Cod post card. Jacknife Cove, sits where Harwich and North Chatham meet, on Pleasant Bay. No bathrooms or snack bar, but so much fun to catch hermit crabs.

cape cod beaches on LEO edit.
Ridglevale Beach

EXPERIENCES

CAPE COD BASEBALL

A Cape Cod summer tradition and an absolute must. All the best college players in the country right before they turn pro! The Chatham A’s at a night game—Cape Cod baseball at its finest. Grab a hot dog and ice cream. The game’s free; make a donation when they pass the hat around.

cape cod baseball on LEO edit.

702 Main St / Chatham / 508.432.6909

WAYSIDE INN OUTDOOR CONCERTS

On Friday evenings, next to the Wayside Inn, they have a band play to large crowds (and dogs). Great for an old-school date night.

wayside inn outdoor concerts on LEO edit.

SULLIVAN GARDEN HIKE

A 0.8 mile lightly-trafficked loop trail that features a lake and is good for all skill levels. The trail is primarily used for hiking, walking, and nature trips.

sullivan garden hike on LEO edit.

88 Old Main St / Chatham

CHATHAM SAILBOAT RENTALS

Right on Ridgevale Beach,a great place for waterfront sailing, kayaking and stand-up paddleboarding, as well as expert-led boat tours and lessons. Sailing guests get complimentary parking for the duration of their rental, and all rates include life jackets, rigging, launching and de-rigging services.

chatham sailboat rentals on LEO edit.
Photo Courtesy of Chatham Sail

FOR THE FAMILY

CHATHAM RAILROAD MUSEUM

Great for kids, and is directly across the way from one of the only playgrounds in town.

chatham railroad museum on LEO edit.
Photo Courtesy of Chatham Railroad Museum

153 Depot Rd / Chatham / 508.945.5780

STORY TIME AT WHERE THE SIDEWALK ENDS

An indy bookstore in a two-story barn with a Children’s Annex full of books and toys. You can sit fireside or outdoors while sipping coffee and browsing books. 10am summer Story Time days with the mother-daughter who own the place (check the schedule first).

story time at where the sidewalk ends on LEO edit.
Photo Courtesy of Where the Sidewalk Ends

432 Main St / Chatham / 508.945.0499

ORLEANS

Nestled in the “elbow” of the cape. No other town on the Cape has a Main Street that runs in a straight line between the calm waters of Cape Cod Bay and the powerful waves of the Atlantic Ocean. Spanning just over four miles, on one end of Main Street sits Rock Harbor, with its sweeping sand flats, where commercial fishing boats and recreational motor craft are a year-round sight in this working harbor.

WHERE TO STAY

A LITTLE INN ON PLEASANT BAY

Perched on picturesque Pleasant Bay, a romantic nine-room boutique Bed & Breakfast with spectacular views of the bay, a private dock and pebble beach for swimming, kayaking, fishing, sailing—and mooring for those who arrive by boat.

a little inn on pleasant bay on LEO edit.
Photo Courtesy of The Little Inn on Pleasant Bay

654 South Orleans Rd / Orleans / 508.255.0780

WHERE TO EAT

HOT CHOCOLATE SPARROW

Great coffee & pastries.

hot chocolate sparrow on LEO edit.
Photo Courtesy of Hot Chocolate Sparrow

5 Old Colony Way / Orleans / 508.240.2230

ROCK HARBOR GRILL

The menu offers a wide variety of dishes from lobster mac & cheese to long-bone short rib pot roast. Or try one of the delicious wood-fired pizza. They have a full bar and outdoor seating.

rock harbor grill on LEO edit.
Photo Courtesy of Rock Harbor Grill

18 Old Colony Way / Orleans / 508.255.3350

SUNBIRD

Uses only the freshest ingredients based on what’s available in season, and makes for a creative, ever-changing menu. They also serve up delicious donuts, bakery items, and coffee drinks.

sunbird on LEO edit.
Photo Courtesy of Sunbird

85 MA-6A / Orleans / 508.237.0354

BEACHES

Skaket Beach, so great for kids. Be there for low tide and the best sunset on the cape. There’s also bathrooms and a snack bar. Nauset Beach, the water can be rough and they often close the water for sharks and seals close to shore, but generations of cape-goers believe it’s the best beach on the cape. There’s a few bathrooms, portable potties and food trucks.

skaket beach on LEO edit.
Skaket Beach

EXPERIENCES

RENTING BIKES

 Bike the trail to PB Boulangerie in Wellfleet, eat at hot chocolate sparrow, then ride one of the rail trails.

renting bikes in cape cod on LEO edit.

NAUSET LIGHTHOUSE

The Nauset Lighthouse is the iconic red-and-white symbol of Cape Cod. It is listed on the National Register of Historic Places. If you venture to only one lighthouse on Cape Cod, this should be it.

nauset lighthouse on LEO edit.
Photo Courtesy of Shutterstock

120 Nauset Light Beach Rd / Eastham / 508.240.2612

SHOPS

PUMP HOUSE SURF SHOP

A surf, skate and beach lifestyle shop where you’ll find quality surfboards, stand-up paddle boards, skimboards, kayaks, bodyboards, skateboards, swimwear, and more. They also offer rentals.

pump house surf shop on LEO edit.
Photo Courtesy of Pump House Surf Shop

9 MA-6A / Orleans / 508.240.2226

FOR THE FAMILY

CAPE ESCAPE ADVENTURE GOLF

18 holes of award-winning mini golf at a nautical-themed course complete with waterfalls, flashing lighthouse, bridges and a koi pond. After the game, get yourself some fish food to let the kids feed the fish.

cape cod escape adventure golf on LEO edit.
Photo Courtesy of Cape Escape Adventure Golf

15 Canal Rd / Orleans / 508.240.1791

CAPE COD CARTWHEELS

Family amusement center featuring go karts, trampolines, air soft shooting gallery, bounce house, whiffle ball cage, batting cages and trampoline basketball. A little something for all ages.

cape cod cartwheels on LEO edit.
Photo Courtesy of Cape Cod Cartwheels

11 S Gages Way / South Dennis / 508.394.6755

ARNOLD’S LOBSTER AND CLAM BAR

Mini golf, ice cream, and great lobster rolls. Worth the drive to get there.

arnold's lobster and clam bar on LEO edit.
Photo Courtesy of Arnolds

3580 US-6 / Eastham / 508.255.2575

HARWICH

Comprised of seven villages, each with their own character: South Harwich, North Harwich, Harwich Port, Harwich Center, East Harwich, West Harwich and Pleasant Lake. It is the quintessential charming Cape Cod town, with an extensive shoreline on Nantucket Sound, and sits right next to Chatham, so it’s easy to move to and fro between the two.

WHERE TO STAY

PLATINUM PEBBLE INN

Adults-only modern bed & breakfast in a quiet neighborhood near wooded walking trails. Beach chairs, towels, and umbrellas are free to guests, as are bicycles for cruising down the Cape Cod Rail Trail. Its eight rooms range from small but elegant to big, stylish spaces embellished with fireplaces and rock ‘n’ roll iconography. 

platinum pebble inn on LEO edit.
Photo Courtesy of Platinum Pebble Inn

186 Belmont Rd / West Harwich / 508.432.7766

WEQUASSETT INN RESORT AND GOLF CLUB

As a guest, you have access to one of Golf Digest’s Top 20 Courses in Massachusetts. With a Championship yardage of 6,954 feet, at the par 72 course, it’s one of the most sought-after rounds of golf on the Cape. A true walking course, golf carts not required. You may find some slow play days, but they do a good job maintaining their goal to keep your round to 4 hours and 15 minutes.

wequassett inn resort and golf club on LEO edit.
Photo Courtesy of Wequassett Inn Resort and Golf Club

2173 MA-28 / Harwich / 508.432.5400

WHERE TO EAT

BRAX LANDING

Long waits but amazing food and a patio right on the harbor.

brax landing cape cod on LEO edit.
Photo Courtesy of Brax Landing

705 MA-28 / Harwich Port / 508.432.5515

OUTER BAR & GRILLE

Waterfront for drinks or dinner outside.

outer bar & grille cape cod on LEO edit.
Photo Courtesy of Outer Bar & Grille

2173 MA-28 / Harwich / 508.432.5400

TWENTY-EIGHT ATLANTIC

Located at the Wequassett Resort, this snazzy spot with views of the water has some of the best high end food in the area (do not skip on that dessert list, trust me) but the stand out is the incredible service.

Photo Courtesy of Twenty-Eight Atlantic

2173 MA-28 / Harwich, MA 02645 / 508.430.3000 

ICE CREAM SPOTS

Take turns between Sundae School Ice Cream and Schoolhouse Ice Cream, both in Harwich Port, and argue over which one is better.

ice cream in cape cod on LEO edit.
Photo Courtesy of Schoolhouse Ice Cream

749 MA-28 / Harwich Port / 508.432.7355

BEACHES

Bank Street Beach, a popular town beach offering a great place for swimming in the warm waters of Nantucket Sound as well as beachcombing for shells with the kids. Red River Beach, also a very popular, big, wide, long beach with very powdery sand and a kayak & canoe launch. It’s a nice beach for families, with plenty of room for the kids to play and gentle waters to splash around in, as well as boogie board.

beaches in cape cod on LEO edit.
Bank Street Beach

FOR THE FAMILY

GRAND SLAM ENTERTAINMENT

Right on the main Route 28, has a small arcade (which includes an air hockey table) and batting cages, a small bumper boats pool and a tiny zip line. The whole thing is crammed onto one small property on the road, but it’s so easy to get to and a surprisingly fun way for the kids to kill an hour. An easy post-beach day stop, as they are open late.

grand slam entertainment cape cod on LEO edit.
Photo Courtesy of Grand Slam Entertainment

322 Main St – Rte 28 / Harwich Port / 508.430.1155

CAP’N KIDS FISHING ADVENTURE

Offers two-hour trips specifically geared towards children. Fish by rod and reel, pull a lobster trap, bait a crab trap and more! 

cap'n kids fishing adventure on LEO edit.
Photo Courtesy of Cap’n Kids Fishing Adventures

715 Route 28 / Harwich Port / 508.430.0066

WELLFLEET

Though only two miles wide, Wellfleet has some of the most beautiful, long stretches of protected beaches on the Atlantic, from Cahoon Hollow to Marconi—all part of iconic Cape Cod National Seashore. Their beloved freshwater Kettle Ponds and warmer bayside beaches are great for easy swimming, paddle boarding and kayaking due to their calmer, flatter waters. Famous for its oysters, it’s a great place to wander in and out of galleries, restaurants and shops. Wellfleet attracts a less tourist-heavy crowd thanChatham, looking for a nature-friendly classic Cape Cod experience.

WHERE TO STAY

THE WAGNER AT DUCK CREEK

This 27-room boutique hotel is situated on Duck Creek, with incredible views overlooking the bay marsh. 

the wagner at duck creek on LEO edit.

70 Main St /Wellfleet / 508.349.9333

WHERE TO EAT

BEACHCOMBER

Live music, cool cocktails, great food, stunning scenery and friendly atmosphere.

beachcomber cape cod on LEO edit.
Photo Courtesy of Beachcomber

1120 Cahoon Hollow Rd / Wellfleet / 508.349.6055

PB BOULANGERIE

A taste of France on Cape Cod.

pb boulangerie on LEO edit.
Photo Courtesy of PB Boulangerie

15 Lecount Hollow Rd / South Wellfleet / 508.349.1600

MAC’S SHACK

Freshest sushi, as well as crudos and oysters on the half shell.

mac's shack on LEO edit.
Photo Courtesy of Mac’s Shack

91 Commercial St / Wellfleet / 508.349.6333

WICKED OYSTER

Fresh Wellfleet oysters and local and sustainable ingredients assembled by chef Sean Woodman and his team.

wicked oyster on LEO edit.
Photo Courtesy of Wicked Oyster

50 Main St / Wellfleet / 508.349.3455

FLYING FISH

Resides on a quiet, tree-shaded side street a short distance from the town center. Because of its out-of-the-way location, it tends to be more of a locals seafood joint.

flying fish cape cod on LEO edit.
Photo Courtesy of Flying Fish

29 Briar Ln / Wellfleet / 508.349.7292

BEACHES

Wellfleet is known for both its Atlantic Ocean beaches with intense surf and its flatter, calmer beaches on the bay side, as well as its beloved Kettle Ponds.

ATLANTIC OCEAN BEACHES

•Cahoon Hollow Beach: Route 6 to Cahoon Hollow Road
•Maguire’s Landing or Lecount Hollow Beach: Route 6 to Lecount Hollow Road for residents
•Marconi Beach: Route 6 to signs at Marconi Beach Road, Cape Cod National Seashore beach, managed by National Park Service
•Newcomb Hollow Beach: Route 6 to Gross Hill Road
•White Crest Beach: Route 6 to Lecount Hollow Road, left to Ocean View Drive

atlantic ocean beaches on LEO edit.

CAPE COD BAY BEACHES

•Mayo Beach: Along Kendrick Avenue, near the Bookstore Restaurant and Mac’s on the Pier, large public parking lot
•Powers Landing: Kendrick Avenue to Chequessett Neck Road, small parking lot
•Duck Harbor Beach: Chequesset Neck to Duck Harbor Road
•Indian Neck Beach: Indian Neck Road to Samoset Avenue to Nauset Road

cape cod bay beaches on LEO edit.

KETTLE POND BEACHES

Often considered the hidden gems of Wellfleet, the crystal clear waters of Wellfleet’s fresh water kettle ponds are popular swimming and recreating areas great for families. They were formed 15,000 years ago from melted glacial deposits that left huge holes, which eventually filled up with water.

•Great Pond: Route 6 to Cahoon Hollow Road – GPS: 585 Cahoon Hollow Road
•Gull Pond: Route 6 to Gull Pond Road, GPS: 140 School House Hill Road
•Long Pond: Route 6 to Long Pond Road, GPS: 505 Long Pond Road

kettle pond beaches on LEO edit.

EXPERIENCE

GREAT ISLAND TRAIL

Great Island Trail and The Gut are a 1.9 mile, moderately trafficked trail that offers the chance to see wildlife and follows sandy stretches between the elevated heights of Great Island and Great Beach Hill, with spectacular vistas which emerge from a pine forest. Some portions are submerged at high tide. Primarily used for hiking, walking, nature trips, and bird watching. A picnic area is adjacent to the parking area.

great island trail on LEO edit.

1440 Chequessett Neck Rd / Wellfleet

WELLFLEET DRIVE-IN THEATRE & FLEA MARKET

Around since 1957, it easily one of the best activities on the Cape, and the only drive-in theater. Showings vary between brand new releases and double features of classics like Jaws and Jurassic Park. There is a real feeling of timelessness at this place. The oldie commercials. The kids working the awesome concessions all look like they could be out of an 80s Spielberg movie. You can also get there early and play a round of mini golf before the movies begin.

The flea market here is also a Cape Cod institution and is open weekends, Wednesdays, and Thursdays from 8am to 3pm. There’s a playground for the kids and a beer garden for whomever doesn’t feel like shopping the giant assortment of 150 sellers.

wellfleet drive-in theatre & flea market on LEO edit.
51 State Highway, Route 6 / Wellfleet / 508.349.7176Photo Courtesy of Wellfleet Drive-In Theatre

51 State Highway, Route 6 / Wellfleet / wellfleetcinemas.com

SHOPS

SICKDAY SURF SHOP

Surf goods, paddleboards, beach toys, apparel, and some skate gear too. In addition, they teach surf lessons and rent all necessities for surfing.

sickday surf shop on LEO edit.
Photo Courtesy of Sickday

3 Main St / Wellfleet / 508.214.4158

TRURO

The town of Truro is made up of two villages: Truro and North Truro. Situated between Provincetown and Wellfleet, Truro is all about the beaches. If you want to be near the fun of Provincetown, but stay somewhere more secluded and nature-friendly, consider staying in Truro. Many of the beach parking lots are small and require a permit, so plan ahead. 

Truro is perhaps overlooked by foodies because it lacks the central downtown area of Provincetown, Orleans, and Chatham and isn’t as easily walkable, but this also adds an air of exclusivity. You gotta be in the know to know where to go. If you’re into finding an off-the-beaten-path restaurant experience, Truro has great high-end restaurants and cool little spots like food trucks and hole-in-the-walls with great to-go sandwiches.

WHERE TO STAY

TRURO BEACH COTTAGES

11 fully renovated beachfront cottages overlooking Beach Point on the Truro/Provincetown line. Each cottage boasts a full kitchen outfitted to prepare your own meals.

truro beach cottages on LEO edit.
Photo Courtesy of Truro Beach Cottages

TRUR 2, 11 / Truro / 774.251.2009

WHERE TO EAT

THE TOP MAST CAFE

Family-friendly summer cafe in the Beach Point neighborhood. American food. Outdoor dining on the patio.

the top mast cafe on LEO edit.
Photo Courtesy of Top Mast Cafe

209 Shore Rd / North Truro / 508.487.2099

SAVORY & SWEET ESCAPE

Cozy local spot serves salads, panini & stone-fired pies plus cupcakes & homemade ice cream for dessert.

savory & sweet escape on LEO edit.
Photo Courtesy of Sweet Escape

316 US-6 / Truro / 508.487.2225

BOX LUNCH

Over 44 years in Truro, this is a delicious fresh-made sandwich spot popular with locals, with two more locations in Wellfleet and P-town.

box lunch cape cod on LEO edit.
Photo Courtesy of Box Lunch

300 US-6 / Truro / 508.487.4545

THE HIGH TIDE KITCHEN

A popular food truck that features an Asian-inspired menu with rice bowls, noodles, salads, and banh mi sandwiches. Fun vibe by the truck, with good music playing and outside tables.

the high tide kitchen on LEO edit.
Photo Courtesy of High Tide Kitchen

8 Highland Rd / North Truro / 774.538.6249

 

MONTANO’S RESTAURANT

Besides traditional Italian fare, they also serve dry-aged prime steaks, locally-caught seafood, and desserts made in their kitchen. A warm and traditional Cape Cod atmosphere while capturing the essence of New England seafare and Italian cuisine.

montano's restaurant on LEO edit.
Photo Courtesy of Montano’s

481 US-6 / North Truro / 508.487.2026

BLACKFISH BISTRO

Rustic brick-walled eatery, formerly a blacksmith shop. Serves out-of-this-world seafood, Wellfleet oysters, and natural beef burgers in an elevated setting. Sit in the back, overlooking the garden.

blackfish bistro on LEO edit.
Photo Courtesy of Blackfish Bistro

17 Truro Center Rd / Truro / 508.349.3399

BEACHES

Longnook Beach, a clothing-optional beach. The enormous dunes give it an isolated and wild feel, popular with nature loving crowds. The sandy trek down the steep and narrow dune path to reach the beach is 50 feet, which isn’t too bad on the way in, but rough at the end of the day when you have to walk up it. Parking is limited, and a town “sticker” aka permit is required. Ballston Beach is an oceanside beach with good surf for boarding. It’s a quieter beach with lots of room to stretch out and spend the day laying out. Corn Hill Beach is a bayside beach, long and narrow, and the waters are calm and great for swimming and popular with families because of its gentle surf and sandbars that appear at low tide. A town beach parking sticker is required.

cape cod beaches on LEO edit.
Ballston Beach

EXPERIENCES

HIGHLAND LIGHT

The original lighthouse in Truro has the distinction of being the first constructed on Cape Cod. The current Highland Light built in 1857, replaced two earlier lighthouses and is the oldest currently on the cape. It is also the tallest of the Cape Cod lighthouses.

highland light on LEO edit.
Photo Courtesy of Shutterstock

27 Highland Light Rd / North Truro / 508.487.1121

BEACH FIRES

Corn Hill Beach and Ballston Beach offer the opportunity to light it up at night. Both beaches offer a limited number of beach fire day permits. You can obtain your permit through the Truro Fire Department. Having a fire on the beach is a memorable experience to have with friends and family, watch the sunset, have a picnic dinner, toast marshmallows, and enjoy the the beach at night.

beach fires on LEO edit.

TRURO VINEYARD

Offers tours of the vineyard and winery and tastings of their finely crafted wines. Food truck on site.

truro vineyard on LEO edit.
Photo Courtesy of Truro Vineyard

11 Shore Rd / North Truro / 508.487.6200

SOUTH HOLLOW SPIRITS

Brings back “the rum-runner days of yore”. Take a tour, and then try a few samples of their locally crafted rums and gin. You can dine while you sip. The gift shop offers specialty cheeses and assorted foods.

south hollow spirits on LEO edit.
Photo Courtesy of South Hollow Spirits

11 Shore Rd / North Truro / 508.487.6200

PAMET CRANBERRY BOG TRAIL

Pamet Cranberry Bog Trail is a 1.9 mile moderately trafficked out-and-back trail running town the Cape Cod National Seashore that offers scenic views and is good for all skill levels. Primarily used for hiking, walking, and nature trips. There is a fee to park and pet restrictions. It is one of 11 trails operated by the Cape Cod National Seashore.

pamet cranberry bog trail on LEO edit.

101 N Pamet Rd / Provincetown / 508.255.3421

BIKING TRAIL/HIKING

For a hiking trail that is a bit more challenging, consider the Ryder Beach Loop. This trail is a 3.2-mile, moderate hike that offers beach views and inland trails. Be sure to pack bug spray to ward off the mosquitos. Head of the Meadow Bike Trail is operated by the Cape Cod National Seashore and is a 2-mile out-and-back trail that runs from High Head Road to Head of the Meadow Beach.

biking and hiking in cape cod on LEO edit.
Cape Cod National Seashore

The closest you can get to a classic links course. Situated high on the bluffs. Panoramic views of the Atlantic Ocean will make it one of your most memorable rounds of the year.

highland links golf on LEO edit.
Photo Courtesy of Highland Links Golf

10 Highland Light Rd / North Truro / 508.487.9201

PROVINCETOWN

Dubbed “Ptown,” it is the liveliest, most bustling town in the Cape, situated on the easternmost part of Massachusetts. It draws a cool, chic crowd of creatives, a thriving artist community, a famously large LGBTQ community, local fishermen, and Boston locals who getaway to this perfectly picturesque, cultured, walkable, bikeable town with its cool book stores, foodie spots, and art galleries as often as possible. Not to mention, the only real nightlife on the Cape.

WHERE TO STAY

CROWNE POINTE INN & SPA

This 19th-century compound centers on a pool and gardens. 35 rooms situated in six large architecturally-restored historic buildings, with a spacious main mansion, award-winning exclusively Kiehl’s spa and fine dining at The Pointe Restaurant

crowne point inn & spa on LEO edit.
Photo Courtesy of Crowne Pointe Inn & Spa

82 Bradford St / Provincetown / 508.487.6767

EBEN HOUSE

A modern boutique bed & breakfast with modern rooms with clawfoot tubs, and a saltwater pool. The main inn is set in a 1776 captain’s house once owned by its namesake, Captain Eben Snow; there are also rooms in an adjoining carriage house and an 1850s Victorian.

eben house on LEO edit.
Photo Courtesy of Eben House

90 Bradford St / Provincetown / 508.487.0386

ASHLEY MANOR

Bed & Breakfast offers two acres of manicured grounds with a spacious backyard patio, gazebo, and tennis court for guests.

ashley manor on LEO edit.
Photo Courtesy of Ashley Manor

3660 Main St / Barnstable / 508.362.8044

AWOL HOTEL

Located at the easternmost point of Provincetown on Cape Cod. Renovated rooms and suites with contemporary decor. Expansive outdoor common area with a pool, guest-only bar serving pool-friendly cocktails, and lounge areas.

awol hotel on LEO edit.
Photo Courtesy of AWOL Hotel

59 Province Lands Rd / Provincetown / 508.413.9820

THE RED INN

This historic, luxurious inn is a local hot spot. Adults-only. Covered in roses that were planted by its original owner, who founded the property in 1916. Dinner here is a must.

the red inn on LEO edit.
Photo Courtesy of The Red Inn

15 Commercial St / Provincetown / 508.487.7334

THE WATERFORD INN

A 15-room guesthouse offering spacious rooms and gorgeous views of the Provincetown Harbor and Pilgrim Monument. The Inn features the most modern of comforts and amenities all while retaining the charm of a circa 1850 Sea Captain’s mansion.

the waterford inn on LEO edit.
Photo Courtesy of The Waterford Inn

386 Commercial St / Provincetown / 508.487.6400

CAPTAIN JACK’S WHARF

Nostalgic cabins on a colorful, historic fishing wharf overlooking the tidal flat basin—with a very loyal clientele who love their well-decorated rooms, each unique, and with fully equipped kitchens.

captain jack's wharf on LEO edit.
Photo Courtesy of Captain John’s Warf

73A Commercial St / Provincetown

PILIGRIM HOUSE INN

Located just off Commercial Street in the Historic District, it puts you at the center of it all. Its Landing Bistro & Bar offers food and artisanal craft cocktails.

pilgrim house inn on LEO edit.
Photo Courtesy of Pilgrim House

336 Commercial St / Provincetown / 508.487.6424

WHERE TO EAT

THE SQUEALING PIG

Known for its beer selection, creative pub grub & occasional live music.

the squealing pig on LEO edit.
Photo Courtesy of The Squealing Pig

335 Commercial St / Provincetown / 508.487.5804

THE CANTEEN

A beachy counter-service spot along Commercial Streets. Grab a table in the large, bustling, sandy patio overlooking Cape Cod Bay. Kids can play on the beach, or have a go on a makeshift swing over the water while waiting for the food to arrive.

the canteen on LEO edit.
Photo Courtesy of The Canteen

225 Commercial St / Provincetown / 508.487.3800

LOCAL 186

Locally sourced meats, seafood, cheeses, house-made condiments, and inventive twists on classic sides, paired with a selection of eclectic beers, cocktails and a carefully curated wine list.

local 186 on LEO edit.
Photo Courtesy of Local 186

186 Commercial St / Provincetown / 508.487.7555

LEWIS BROTHERS HOMEMADE ICE CREAM

Laid-back counter serve offering traditional & boozy housemade ice cream, plus sorbet & smoothies. Homemade ice cream is made fresh daily.

lewis brothers homemade ice cream on LEO edit.
Photo Courtesy of Lewis Brothers Homemade Ice Cream

310 Commercial St / Provincetown / 508.487.0977

MAC’S FISH HOUSE

Upscale yet casual, a family-friendly, more intimate dining experience away from the bustle of Commercial Street with a place to park your car for free. Fresh sushi, locally-sourced seafood classics and inventive seasonal specials in the dining room, garden patio or indoor and outdoor bars.

mac's fish house on LEO edit.

85 Shank Painter Rd / Provincetown / 508.487.6227

SAL’S PLACE

Authentic Italian dinning right on the water that’s been open for 50 years.

sal's place on LEO edit.
Photo Courtesy of Sal’s Place

99 Commercial St / Provincetown / 508.487.1279

SPLINDER’S

Spindler’s comes from Boston-based, James Beard Award-winning Chef Barbara Lynch. Its menu sits at the crossroads of French and Italian.

splinder's on LEO edit.
Photo Courtesy of Splinders

386 Commercial St / Provincetown / 508.487.6400

FAR LAND PROVISIONS

Provincetown’s favorite corner store & deli featuring on-site bakery, prepared foods, and made-to-order breakfast and lunch sandwiches.

far land provisions on LEO edit.
Photo Courtesy of Far Land Provisions

150 Bradford St / Provincetown / 508.487.0045

KUNG FU DUMPLINGS

Steamed dumplings freshly handmade every day.

kung fu dumplings on LEO edit.
Photo Courtesy of Kung Fu Dumplings

293 Commercial St / Provincetown / 774.538.7106

PROVINCETOWN PORTUGUESE BAKERY

Most of the recipes have been handed down from generation to generation, including original recipes from the founders of the bakery in 1901. A collection gathered through the years and common in Portugal.

provincetown portuguese bakery on LEO edit.
Photo Courtesy of Provincetown Portuguese Bakery

299 Commercial St / Provincetown / 508.487.1803

POP + DUTCH

A sandwich shop and pint-sized specialty grocery.

pop + dutch on LEO edit.
Photo Courtesy of Pop + Dutch

147 Commercial St / Provincetown / 774.538.6472

MISTRALINO

Authentic Tuscan food, located in the heart of town. Rustic wooden beams, antique chandeliers, and brick fireplaces. 

mistralino on LEO edit.

133 Bradford St / Provincetown / 774.593.5945

BEACHES

Herring Cove Beach, the only Cape Cod National Seashore beach that is on the Cape Cod Bay side of the Cape. The waves are more gentle and the water temperatures a bit warmer than along the Atlantic Ocean. Race Point Beach, features dunes, lighthouses, and free whale watching on its beach as well as dune tours.

cape cod beaches on LEO edit.
Race Point Beach

EXPERIENCES

PROVINCETOWN LIGHTHOUSES

Woodend Light, If you’re looking for a hike on the beach, a trip to Wood End Light would be perfect. At the northern end of Cape Cod, this lighthouse, built in 1862, steered those at sea through the sandbars to safety. Isolated on a strip of sand, Wood End Light sits alone. The light was automated in 1961 and has run on solar power since 1981. You can walk to the Wood End Light from Provincetown in about 30 minutes. If you take the breakwater route, watch for rough seas. Race Point Light, also near Provincetown, it is listed on the National Register of Historic Places. The first lighthouse in this location was built in 1816, and the current tower dates to 1876. If you’re looking to experience a stay in a lighthouse, Race Point is available. It’s run by the American Lighthouse Foundation and offers overnight stays. No that to get to the lighthouse, you have to walk for about 45 minutes on a sandy beach. You could also rent a vehicle with four-wheel drive.

provincetown lighthouses on LEO edit.
Race Point Light. Photo Courtesy of Shutterstock

PROVINCETOWN MUSEUM

In 1910, the Cape’s first building built to house a museum opened at the base of the monument, to educate the public about Provincetown’s role in Pilgrim history and American history. The permanent exhibits retain the charm of an old-fashioned history museum. Exhibits highlight the arrival of the Mayflower Pilgrims, the town’s rich maritime history, the early days of modern American theater in Provincetown, and the building of the monument.

provincetown museum on LEO edit.
Photo Courtesy of Provincetown Museum

1 High Pole Hill Rd / Provincetown / 508.487.1310

PILGRIM MONUMENT

The Pilgrim Monument was founded in 1892 as the Cape Cod Pilgrim Memorial Association—Cape Cod’s oldest not-for-profit organization. Its purpose is to commemorate the Mayflower Pilgrims’ first landing in the New World in Provincetown, in November 1620. Here, the Pilgrims spent 5 weeks exploring the tip of Cape Cod, before they sailed on to Plymouth. They also drew up and signed the Mayflower Compact, which established the rule of law for the new land.

pilgrim monument on LEO edit.

 1 High Pole Hill Rd / Provincetown / 508.487.1310

HERRING COVE TIDAL LAKE KAYAK TOUR

Sign up for the Herring Cove Tidal Lake kayak tour at Provincetown Aquasports. Plan this a day ahead. You can “ride the tide” in and out of peaceful tidal “rivers” during this two-hour guided tour. It doesn’t require experience and launches at The Moors at the end of Route 6.

herring cove tidal lake kayak tour on LEO edit.
Photo Courtesy of Provincetown Aquasports

333R Commercial St #1 / Provincetown / 508.413.9563

SHOPS

MAP

This cool men’s shop manages to feel both modern and vintage, with its chic but rugged interior, cool clothing brands, accessories, and lots of great gift items you’ll want to buy just because.

map shop cape cod on LEO edit.

188 Commercial St / Provincetown / 508.487.4900

ARNOLD’S BIKE SHOP

A town favorite, they specialize in bike rentals, repairs, sales and accessories. Another good spot to rent bikes would be Provincetown Bike Shack.

arnold's bike shop on LEO edit.
Photo Courtesy of Arnold’s Bike Shop

329 Commercial St / Provincetown / 508.487.0844

TIM’S USED BOOKS

Cool, quite little vintage book store off the main drag of town, with interesting, rare selections and fun to just browse. 

tim's used books on LEO edit.
Photo Courtesy of Tim’s Used Books

242 Commercial St / Provincetown / 508.487.0005

FALMOUTH

One of four towns on the Upper Cape, it’s beloved for its beach-town vibe, with a lot of hotels and private beaches, a busy downtown, and local winery. Due to its vicinity to the city, it tends to get a lot of Boston families coming in for the weekend. It’s also the gateway to Martha’s Vineyard and Nantucket so it gets a lot of passing-through action.

WHERE TO STAY

AUTOCAMP

Modern Airstream Suites, spacious canvas Tents, and roomy X Suites rely on ingenious, compact designs to provide every amenity you need, without sacrificing a sense of space and indulgence.

autocamp cape cod on LEO edit.
Photo Courtesy of Autocamp

836 Palmer Ave / Falmouth / 855.203.1518

INN ON THE SQUARE

Boutique charm meets coastal luxury. Minutes from Cape Cod’s beaches and three blocks from the ferries to Martha’s Vineyard. After a day exploring the area, take a dip in the skylit pool, or grab lunch at the restaurant.

inn on the square on LEO edit.
Photo Courtesy of Inn on the Square

40 N Main St / Falmouth / 508.457.0606

INN ON THE SOUND

12 well-decorated guest rooms with ocean views and delicious homemade breakfasts.

inn on the sound on LEO edit.
Photo Courtesy of Inn on the Sound

313 Grand Ave / Falmouth / 508.457.9666

WINGS NECK LIGHTHOUSE

It’s a once in a lifetime experience to stay in a lighthouse, but most are better in theory than in reality, as they tend to be very low-key, rustic affairs. Wings Neck on the other hand is a historic and unique property but with a completely (and really well) renovated, fully functional three-bedroom keepers home, and with all of the conveniences you need. Not to mention one of the best and most traditionally New England views of the Atlantic Ocean imaginable. Formerly a US Coast Guard Lighthouse, it’s just a few feet from the water. Exploring the rocks and the shore in front of the house is a guest favorite.

wings neck lighthouse on LEO edit.

1 Lighthouse Lane / Pocasset, MA 02559

WHERE TO EAT

ANEJO MEXICAN BISTRO

Unique take on fresh Mexican cuisine and cocktails offered in a fun, airy atmosphere

anejo mexican bistro on LEO edit.
Photo Courtesy of Anejo Mexican Bistro

599 Main St / Hyannis / 774.470.5897

THE GLASS ONION

1920s vibe pairs refined New American cooking with global wines.

the glass onion on LEO edit.
Photo Courtesy of The Glass Onion

37 N Main St / Falmouth / 508.540.3730

BEARS IN BOOTS GASTRO CLUB

A warm, comfortable, well-designed spot for skillfully-made comfort food usually reserved for fine dining restaurants.

bears in boots gastro club on LEO edit.
Photo Courtesy of Bears in Boots

285 Main St / Falmouth / 508.444.8511

DOGGZ AND HOGGZ

Specialty hot dogs, the best slow-smoked BBQ, and their very own recipe for Stuffed Quahogs.

doggz and hoggz on LEO edit.
Photo Courtesy of Doggz and Hoggz

781 Main St / Falmouth / 508.548.3663

PICKLE BAR KITCHEN

Bright cafe for comfort-food breakfast, plus lunch & brunch drinks dished up in a historic building. Sit for a meal or grab a snack for the road.

pickle jar kitchen on LEO edit.
Photo Courtesy of Pickle Jar Kitchen

 170 Main St / Falmouth / 508.540.6760

BEN & BILL’S CHOCOLATE EMPORIUM

Quality candies and chocolates made with the original recipes, and numerous flavors of ice cream.

ben and bill's chocolate emporium on LEO edit.
Photo Courtesy of Ben & Bills Chocolate Emporium

209 Main St / Falmouth / 508.548.7878

QUAHOG REPUBLIC DIVE BAR

Serves a full menu till 12:30am nightly. Try the famous Aussie or Island Burger, Stuffed Quahog, Quahog Chowder and the very popular crunchy cod Fish and Chips. Sample a frozen drink, fresh squeezed cocktail or one of the 10 beers on tap. 

guahog republic dive bar on LEO edit.

97 Spring Bars Rd / Falmouth / 508.540.4111

OSTERIA LA CIVETTA

Fresh, simple, authentic Northern Italian cuisine. Casual atmosphere with a great outdoor space.

Photo Courtesy of Osteria La Civetta

113 Main St / Falmouth / 508.540.1616

BEACHES

OLD SILVER BEACH

Old Silver Beach, a popular spot for swimming and beach combing. Falmouth Heights Beach, a very popular beach on Nantucket Sound. Restaurant and concessions are just across the street and there are park benches and a grassy area overlooking the beach.

old silver beach on LEO edit.

EXPERIENCES

NOBSKA LIGHT

Stands on a hillside at the western tip of Cape Cod, facing the Atlantic Ocean and the entrance to Buzzards Bay. From a vantage point on the lawn of the lighthouse, you can see Martha’s Vineyard and Nantucket Sound. Ferries steam out and back from these islands.

nobska light house on LEO edit.
Photo Courtesy of Shutterstock

233 Nobska Rd / Falmouth / 774.763.6453

THE CAPE CLUB

Built over the old Ballymead Club, it has been completely reimagined with all new greens. Remodeled fairways have transformed the golfers tee-to-green playing experience. Has a newly renovated clubhouse and is open to the public, but has a private club feel.

the cape club on LEO edit.
Photo Courtesy of The Cape Club

125 Falmouth Woods Rd / East Falmouth / 508.540.4005

RIDEAWAY ADVENTURES

Kayak, paddle board, and bike rentals. Also offers kayak and paddle board tours.

rideaway adventures on LEO edit.

259 Shore Drive / Mashpee / 508.247.0827 

THE KNOB

Located in Woods Hole, continues to be a major attraction to the public for its nature walk, birding, marsh, coastal bank and its spectacular views of Quissett Harbor and Buzzards Bay.

the knob on LEO edit.

SHINING SEA BIKEWAY

Hugs the coast from Falmouth to Woods Hole and then beyond to North Falmouth, winding along the Vineyard Sound shoreline. Ideal for casual and beginner cyclists, it was built on a former railroad right-of-way. The paved path is level for nearly its entire 10.7-mile distance with only a slight grade in certain spots. Lined with familiar Cape Cod flower and tree species, it makes for a great ride from Falmouth to scenic Woods Hole.

shining sea bikeway on LEO edit.

WOODS HOLE VILLAGE

The charming New England village of Woods Hole lies at the far southwestern tip of Cape Cod, with Buzzards Bay to its west and Vineyard Sound to its east. Because of its excellent harbor, it became a center for whaling, shipping, and fishing prior to its dominance today by tourism and marine research.

woods hole village on LEO edit.

FOR THE FAMILY

PIRATE’S COVE

The Cape has no shortage of mini golf, but this is a favorite. A pirate-themed mini-golf chain with 18-hole, landscaped courses, good for all ages, as well as waterfalls, tunnels, scary pirate areas to walk through, and funny pirate music. There are picnic tables in the back. Very clean and tidy, and beloved by kids.

pirate's cove on LEO edit.
Photo Courtesy of Pirates Cove

728 Main St / South Yarmouth / 508.394.6200

CATAUMET MINI GOLF AND ICE CREAM

Family-fun destination featuring a mini-golf course, bumper boats, ice cream & a mini-batting cage.

cataumet mini golf and ice cream on LEO edit.

1370 MA-28A / Cataumet / 508.326.8160

CAPE COD INFLATABLE PARK

Wet and dry inflatable rides for kids (and adults). Packed with large themed inflatable slides, bounce houses, games, Shark Bites restaurant, 9-hole mini golf course, arcade and more.

cape cod inflatable park on LEO edit.
Photo Courtesy of Cape Cod Inflatable Park

518 Main Street Route 28 / West Yarmouth / 508.771.6060

DAY TRIPS

WHALE WATCHING & SEAL TOURS

Whale watching is a Cape Cod rite of passage and a surprisingly moving experience. Find one and do it. Take the kids. Seal tours are great fun too. Favorites on the Cape include Flyers Boat Seal Tours, Whale Watch Dolphin Fleet, Captain John Boats.

whale watching and seal tours cape cod on LEO edit.
Photo Courtesy of Captain John Boats

NANTUCKET

Postcard-perfect little island with pristine beaches, accessible only by ferry. Visit Historic Downtown and Siasconset.

nantucket on LEO edit.

MARTHA’S VINEYARD

Take the Island Queen ferry from Falmouth to Oak Bluffs in Martha’s Vineyard. This 35-minute passenger-only ferry leaves from the Falmouth Inner Harbor. Consider the Steamship Authority out of Woods Hole if you are planning to take a vehicle over. Explore the historic island town divided into 6 towns: Tisbury, Edgartown, Oak Bluffs, West Tisbury, Chilmark, and Aquinnah (the most popular being Edgartown and Oak Bluffs)—filled with gorgeous beaches and delicious restaurants.

martha's vineyard on LEO edit.
Photo Courtesy of Getty