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.
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.
Guide Tip: click on the town names in bold below to skip right to their guides.
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.
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).
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.
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.
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 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.
297 Shore Rd / Chatham / 508.945.0096
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.
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.
15 Chatham Bars Ave / Chatham / 508.945.3545
THE CHATHAM SQUIRE
Best place for chowder and a Sam Adams. Very kid-friendly.
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.
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.
2624 Main St / Brewster, MA 02631 / 774.323.0605
Good for breakfast and kid friendly.
75 Old Harbor Rd / Chatham / 508.945.4380
Great for an adult night out. Sandwiched right between Chatham and Harwich.
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.
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.
297 Shore Rd / Chatham / 508.945.0096
A popular divey diner for breakfast.
1591 Main St / Chatham / 508.945.3964
THE RED NUN
Local fisherman spot to eat the best clam chowder.
746 Main St / Chatham / 508.348.0469
Everyone loves this spot for 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.
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.
2022 Main St / Chatham / 508.432.9439
Modern bistro cuisine. Wood-fired thin crust pizza, good pasta, serious steaks, and a lively bar scene.
907 Main St / Chatham / 508.945.9988
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.
1260 Main St / Chatham / 508.945.9777
It’s at the tiny Chatham airport, so you can eat delicious breakfast while watching planes take off.
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.
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).
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.
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.
10 Chatham Bars Ave, Chatham, MA 02633 / 774.836.7217
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 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.
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.
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.
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.
FOR THE FAMILY
CHATHAM RAILROAD MUSEUM
Great for kids, and is directly across the way from one of the only playgrounds in town.
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).
432 Main St / Chatham / 508.945.0499
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.
654 South Orleans Rd / Orleans / 508.255.0780
WHERE TO EAT
HOT CHOCOLATE SPARROW
Great coffee & pastries.
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.
18 Old Colony Way / Orleans / 508.255.3350
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.
85 MA-6A / Orleans / 508.237.0354
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.
Bike the trail to PB Boulangerie in Wellfleet, eat at hot chocolate sparrow, then ride one of the rail trails.
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.
120 Nauset Light Beach Rd / Eastham / 508.240.2612
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.
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.
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.
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.
3580 US-6 / Eastham / 508.255.2575
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.
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.
2173 MA-28 / Harwich / 508.432.5400
WHERE TO EAT
Long waits but amazing food and a patio right on the harbor.
705 MA-28 / Harwich Port / 508.432.5515
OUTER BAR & GRILLE
Waterfront for drinks or dinner outside.
2173 MA-28 / Harwich / 508.432.5400
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.
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.
749 MA-28 / Harwich Port / 508.432.7355
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.
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.
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!
715 Route 28 / Harwich Port / 508.430.0066
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.
70 Main St /Wellfleet / 508.349.9333
WHERE TO EAT
Live music, cool cocktails, great food, stunning scenery and friendly atmosphere.
1120 Cahoon Hollow Rd / Wellfleet / 508.349.6055
A taste of France on Cape Cod.
15 Lecount Hollow Rd / South Wellfleet / 508.349.1600
Freshest sushi, as well as crudos and oysters on the half shell.
91 Commercial St / Wellfleet / 508.349.6333
Fresh Wellfleet oysters and local and sustainable ingredients assembled by chef Sean Woodman and his team.
50 Main St / Wellfleet / 508.349.3455
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.
29 Briar Ln / Wellfleet / 508.349.7292
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
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
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
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.
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.
51 State Highway, Route 6 / Wellfleet / wellfleetcinemas.com
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.
3 Main St / Wellfleet / 508.214.4158
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.
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.
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.
316 US-6 / Truro / 508.487.2225
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.
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.
8 Highland Rd / North Truro / 774.538.6249
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.
481 US-6 / North Truro / 508.487.2026
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.
17 Truro Center Rd / Truro / 508.349.3399
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.
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.
27 Highland Light Rd / North Truro / 508.487.1121
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.
Offers tours of the vineyard and winery and tastings of their finely crafted wines. Food truck on site.
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.
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.
101 N Pamet Rd / Provincetown / 508.255.3421
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.
HIGHLAND LINKS GOLF
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.
10 Highland Light Rd / North Truro / 508.487.9201
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.
82 Bradford St / Provincetown / 508.487.6767
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.
90 Bradford St / Provincetown / 508.487.0386
Bed & Breakfast offers two acres of manicured grounds with a spacious backyard patio, gazebo, and tennis court for guests.
3660 Main St / Barnstable / 508.362.8044
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.
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.
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.
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.
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.
336 Commercial St / Provincetown / 508.487.6424
WHERE TO EAT
THE SQUEALING PIG
Known for its beer selection, creative pub grub & occasional live music.
335 Commercial St / Provincetown / 508.487.5804
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.
225 Commercial St / Provincetown / 508.487.3800
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.
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.
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.
85 Shank Painter Rd / Provincetown / 508.487.6227
Authentic Italian dinning right on the water that’s been open for 50 years.
99 Commercial St / Provincetown / 508.487.1279
Spindler’s comes from Boston-based, James Beard Award-winning Chef Barbara Lynch. Its menu sits at the crossroads of French and Italian.
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.
150 Bradford St / Provincetown / 508.487.0045
KUNG FU DUMPLINGS
Steamed dumplings freshly handmade every day.
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.
299 Commercial St / Provincetown / 508.487.1803
POP + DUTCH
A sandwich shop and pint-sized specialty grocery.
147 Commercial St / Provincetown / 774.538.6472
Authentic Tuscan food, located in the heart of town. Rustic wooden beams, antique chandeliers, and brick fireplaces.
133 Bradford St / Provincetown / 774.593.5945
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.
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.
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.
1 High Pole Hill Rd / Provincetown / 508.487.1310
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.
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.
333R Commercial St #1 / Provincetown / 508.413.9563
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.
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.
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.
242 Commercial St / Provincetown / 508.487.0005
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
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.
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.
40 N Main St / Falmouth / 508.457.0606
INN ON THE SOUND
12 well-decorated guest rooms with ocean views and delicious homemade breakfasts.
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.
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
599 Main St / Hyannis / 774.470.5897
THE GLASS ONION
1920s vibe pairs refined New American cooking with global wines.
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.
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.
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.
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.
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.
97 Spring Bars Rd / Falmouth / 508.540.4111
OSTERIA LA CIVETTA
Fresh, simple, authentic Northern Italian cuisine. Casual atmosphere with a great outdoor space.
113 Main St / Falmouth / 508.540.1616
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.
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.
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.
125 Falmouth Woods Rd / East Falmouth / 508.540.4005
Kayak, paddle board, and bike rentals. Also offers kayak and paddle board tours.
259 Shore Drive / Mashpee / 508.247.0827
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.
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.
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.
FOR THE FAMILY
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.
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.
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.
518 Main Street Route 28 / West Yarmouth / 508.771.6060
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.
Postcard-perfect little island with pristine beaches, accessible only by ferry. Visit Historic Downtown and Siasconset.
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.