Boston by Casey Affleck

For the record, what follows is nostalgia, false memories, and generalizations. But it’s all true. I grew up in Cambridge, Massachusetts, across the Charles River from Boston proper. Cambridge was one of the most diverse, multicultural cities in America. It was a beautiful, colorful, vibrant place. People from all over the world lived there, all mixed-up together. It is the place I was born and will return to, God willing. It is the city with the smells and sounds and tastes and people I love the most.

Despite how much I loved it, when I look at old photos, I often look like this:

casey affleck classroom on LEO edit
Photo Courtesy of Casey Affleck

I’m in the front in the blue shirt. My best friend was Michael, the tall kid in the red shirt, whose family came from Barbados. Through the middle school years, anytime we weren’t in school we were roaming the streets like Dickensian urchins.

In the ‘90s, Cambridge got rid of rent control. Families who had lived there for four or five generations were squeezed out. Now the city is gentrified; but when I was growing up there, it was scrappy and beautiful. It was mostly working people, except for West Cambridge—where wealthy families lived, where professors lived. Where Cornel West, Yo-Yo Ma, and the Governor lived. East Cambridge was working-class Portuguese families, butcher shops, funeral parlors, and tow yards. Cambridgeport, where I lived, was mostly poor, Italian, Black, Greek, and Irish families. North Cambridge had some big housing projects and the school where my mom taught fifth grade—in a gigantic cement structure called The Tobin School that felt like it was far away because I would have to take a train AND a bus to get there. In reality, it’s like three miles from where we lived.

This is me hanging out in her classroom:

casey affleck young on LEO edit
Photo Courtesy of Casey Affleck

As people and places evolve, the past always reveals blemishes unseen at the time. However, Massachusetts manages, as time unfolds, to be a place that was so often on the right side. Not always, but often enough that I am proud to be from Cambridge, Massachusetts, no matter what.

From Massachusetts came the first national publication denouncing slavery, America’s “first feminist”, and The Cambridge Woman’s Suffrage League, which formed in 1886. My high school had the first girl to play tackle football in that division. Cambridge voted-in the first openly gay African-American mayor in our country. Right now our mayor is a very popular and forward-thinking Muslim woman who immigrated from Pakistan named Sumbul Siddiqui. We have marvels of architecture, science, and tech. It was in Cambridge that the very first email was ever sent (and received). And every year the Red Sox stand up to the wealthier bullies from the Bronx. These are all things we are immensely proud of, but nobody is resting on these laurels.

 I am going to tell you about the places I remember fondly, whether they are still there or not.

Luckily, the city’s history isn’t going anywhere, and it hasn’t lost all of its charms. It is a place best seen by walking. So just walk. It’s also seasonal. Different activities for different seasons. But if you can hoof it for a few miles do this: start at the Old North Church and go by Paul Revere House, through Faneuil Hall, by The Old State House through Boston Common, through the Back Bay, go left and pass through Roxbury, another left, and go through South Boston till you hit the water and go left till you hit the Children’s Museum. Sit down and relax. If you just want a path, walk that. Map it or wander around. The city is full of little back streets with lots of character.


When looking for things to do and see in the area, you can ask ten people and get ten different answers. You will get a long list of historical buildings, or you will get names of some of the country’s prettiest parks, or you will get pointed toward the campuses of some of the very best schools in the world. But for every Bunker Hill, there are ten other places you haven’t heard of. So I am going to tell you about the places I remember fondly, whether they are still there or not. The thing about Boston is you can miss all the best stuff, and you will still leave thinking it is one of the best cities on Earth. Have fun. 

Pinocchio Pizza, Harvard Square. I asked my son to describe it. He says, “the food is good but the vibe is fire, old school; whatever, just get a slice and sit on the ground. That’s why I like it.”  I have no idea why he wants to sit on the ground, but I guess that’s part of the charm of the place. We’re both vegan so we both scrape the cheese off and eat bread and sauce. That should tell you something.

Oleana Restaurant on Hampshire Street in Cambridge. Chef Ana Sortun is a baller. The food is Turkish inspired, and it is delicious. Always. Friendly people, pretty inside, and it is in a nice residential neighborhood. My dad lived in an apartment a few blocks away behind a Store 24 until he was evicted back in 1989.

Maharaja, Harvard Square. Incredible Indian food. And it has one of the only third-story views of Harvard Square.

Veggie Galaxy is great diner food. It is vegan. It has breakfast, lunch, dinner, milkshakes and other deserts. All day and all night food that is filling and really good.

Life Alive Organic will serve you the healthiest and heartiest meal you can find anywhere. It’s across the street from City Hall, the post office, and the oldest YMCA in the country.

Cantab Lounge, where my dad was a bartender, and then a janitor when he was too drunk to be a bartender. I drank six thousand ginger ales, sitting in the corner at a sticky table while he worked. Forever it was a bar for postal workers that opened at 10 am, where alcoholics ate hard-boiled eggs from jars that had been sitting on the bar top for two weeks. A couple of days after initially writing this, I got an email from the owner. It is being sold after tens of thousands of years. I don’t know why I care because I don’t exactly have any fond memories from the place, but seeing the brick-and-mortar of your childhood torn down is a kind of mid-life, coming-of-age moment. Life is change. 

Darwins Ltd coffee shop and attached mini-grocer and sandwich spot. If you get a coffee and then walk west two blocks on Mt. Auburn St. you will discover on your right a nice little park with a fountain to hang out. It is called Longfellow Park. Or you can look to your left and you will see the Charles River, and you can stroll there.

Fomu for dessert.

Zhu Pan Asian Cuisine and True Bistro for good vegan food.

Newbury Comics is famous and cool. Million Year Picnic is for comic connoisseurs. They are both great. And they were both plagued by roving bands of middle school thieves in my day. The most notorious was named Mathew Maher. He is now a well-known theater actor on Broadway and appeared in the comic book movie Captain Marvel. But back then he stole shit.

Harvard Coop is the best place to browse for books. Especially the kids section. We spend hours there and nobody kicks us out.

After the game ended everyone would come out and buy sausages [from me] on their way home, then I would clean up and go into a bar outside the park, where my boss was drinking and I’d wait till he was done so I could get a ride home. I was 12 years old. A couple of years ago I threw out the first pitch. Life is change.

The Isabella Stewart Gardner Museum is my favorite museum in town, maybe anywhere. It was once her home and it features an indoor garden that is perfect. It also has a great collection of art from around the world.  Back on March 18, 1990, two famous paintings were stolen from the museum. As I remember it, a couple of guys showed up in the morning in police uniforms and the guard let them in. They tied the guard up and took a dozen paintings—Vermeer, Rembrandt, Degas—and vanished. The FBI never found them and never found the art. There are two plaques below two empty spaces on the walls to this day. On some days, classical musicians perform in random rooms while you walk around. You won’t want to leave.

Fenway Park. Greatest professional sports arena of any kind. I used to sell sausages in front of the Cask ‘N Flagon, a bar behind The Green Monster. It is the best baseball bar in the country. When everyone was in the park watching the game, and there was nobody buying food, I would go in and find a seat and watch the game with whoever I was working with; I have seen hundreds of games from every part of the park. After the game ended everyone would come out and buy sausages on their way home, then I would clean up and go into a bar outside the park, where my boss was drinking and I’d wait till he was done so I could get a ride home. I was 12 years old. A couple of years ago I threw out the first pitch. Life is change.

Plimoth Plantation is a living museum in Plymouth, which is 40 minutes from Boston. It is amazing. The actors working there are some of the best I have seen anywhere. If you are even mildly interested in history you have to go there. 

Fresh Pond is where you can go running or biking. Two and a half-mile loop. Or you could hit The Emerald Necklace which is a great run that hits many of the best green areas, Franklin Park included. When we were young we would hop the fence and swim in the water. That isn’t done anymore ever, and everyone has grown up and leading better, more responsible lives.  

John Weeks Footbridge is a very pretty, very old, brick walking bridge that spans the Charles River. Watching the Charles Regatta from here is awesome. That is in the Fall. But it’s also great any night.  

The King School is a grade school not too far from there. It has maybe the best playground in the city. If you are there in the summer you can just walk on. When I was a kid, the King School is where a girl went who I was head over heels in love with. I finally got a shot at winning her heart in my early twenties and blew it. 

Mount Auburn Cemetery is beautiful if you like that kind of thing. Lots of cool people are buried there, and the trees and stones are really nice. It’s a maze but just walk uphill. You will reach a monument with a great view of the city.

The American Repertory Theater puts on good plays. I grew up going there cause a friend of my mother’s directed many of the shows and could sneak us in the back. I wasn’t the adult making that decision; had I known better I would have scraped together the ticket price and supported the arts.

Boston Common is beautiful but you have to avoid all the shopping around it. If you have to shop go to:

NOMAD on Mass Ave in Cambridge is a store that you shouldn’t miss. In a world lost to chain stores and general homogenization of everything, Nomad is the real deal. Deb Colburn has been curating this place since I was ten. It is her store, and she has been trying to wake people up to folk art from around the world since Reagan was in office.

Bodega is a hidden high-end sneaker and casual wear store that must be entered through an unmarked door inside a bodega on a nearby side street. It’s cool how they have done it. Great presentation. Kids will like it.


There are lots of things you can force your kids to do—things they won’t like the sound of at first, but will ultimately enjoy.

casey affleck on LEO edit
Photos Courtesy of Casey Affleck


  • On a rainy day, hop on the T and ride around town all day reading comics. Then stand outside in the warm rain (kids from LA don’t get this much).
  • Looking at murals. Cambridge has great murals everywhere. They are old and, incredibly, not vandalized. This one has been on this wall near the river since I was a kid. The child is mine and he is sick of walking around Cambridge.
  • If you feel like a pilgrim hit the gift shop at Plimoth Plantation.
  • Playing chess at Leavitt & Pierce Tobacco. You can inhale the scent of pipe tobacco without smoking it, and rent a chess set, clock, and table for $2 an hour in a beautiful old, wood-paneled shop with great ambiance.
  • Going to the oldest YMCA in the country.
  • Kayaking on the Charles River. You can get your kayak on Soldiers Field Rd. Take it east under all the bridges until you get to the inlet at Kendell Sq. It will all be clear. It will take about an hour.
  • Climbing the stairs at Harvard Football Stadium.
  • Reading books at the Harvard Coop.


If you wanna go a little farther, go out to Gloucester for the day. Swim, eat, walk around, go back.

Whale watching sounds like a lame tourist trap but seeing whales up close will change the way you think about life on Earth.

You can take the ferry from Downtown Boston to Provincetown. It is a great place to visit or stay a few days while in town. Ptown is the eastern-most point on the continent. I might be making that up, but it’s close. It’s an arm that sticks out into the Atlantic. It’s really lovely there with a great vibe all around. You can’t have a bad time and everyone is super happy to be there. The beaches are all beautiful.  Sharks mostly only eat the seals and won’t come any closer to shore than two feet—but if you want to see a great white up close, we can make that happen.

Cape Cod has some great flea markets.  If you plan on spending time on vacation with your family you can find some essentials, like a medieval battle helmet, at the flea market.


30 minutes on the local train line from downtown. Made famous by the Salem witch trials; a fun place to visit and walk around for about 128 minutes. Newburyport and Rockport lines, which depart from Boston’s North Station, stop at the Salem station. You can go into the homes of people who lived during the witch hunt.

The House of the Seven Gables, made famous by American author Nathaniel Hawthorne‘s novel The House of the Seven Gables, is a 1668 colonial mansion in Salem, Massachusetts named for its gables. The house is now a non-profit museum, with an admission fee charged for tours, as well as an active settlement house with programs for children. It was built for Captain John Turner and stayed with the family for three generations.

The Jonathan Corwin House in Salem, Massachusetts, known as The Witch House, was the home of Judge Jonathan Corwin. It is the only structure still standing in Salem with direct ties to the Salem witch trials of 1692, thought to be built between 1620 and 1642. Corwin bought it in 1675 when he was 35, and he lived there for more than 40 years. The house remained in the Corwin family until the mid-19th century and is located in the McIntire Historic District.


Lastly, for centuries, Cambridge has been a mecca for artists, especially writers. Here are some spots to see if you like that kind of thing:

The corner of JFK Street and 1390 Massachusetts Avenue. This is a good spot. Here is why: America’s FIRST PUBLISHED POET was a woman named Anne Bradstreet who died in 1672 and lived on this spot! It went through lots of changes, and 300 years later, by the time I was walking around, it became a great burger place called THE TASTY. In 1996 or whatever, The Tasty appears in the movie Good Will Hunting in the scene when Matt Damon kisses Minnie Driver. It might have also appeared in the film Love Story back in the 70s. I mix them up. Now it is a CVS.  God help us.  

The Longfellow House. Henry Wadsworth Longfellow lived at 105 Brattle Street. The great poet taught at Harvard and lived in the Georgian mansion from 1837 until his death in 1882. Before the author, George Washington used the house as his headquarters during the Siege of Boston. The house is open to the public, and it is where I had my eighth-grade graduation ceremony. The mayor attended and forgot the name of our school in his address to the kids. I heard people mutter that he was drunk. I can’t blame him. I had my first drinks hours before that ceremony.

71 Cherry Street, Cambridge. The woman considered to be American’s FIRST feminist, Margaret Fuller, was born and lived here.

29 Buckingham Street. Thomas Wentworth Higginson—the author, abolitionist, and minister, who was born in Cambridge and was close friends with Emily Dickinson—lived here.

Henry and Alice James lived at 20 Quincy Street. The house was knocked down in 1930 and the Harvard Faculty Club was erected there.

W.E.B. DuBois lived at 20 Flagg Street. The writer and pioneer of civil rights rented a room in this Cambridgeport home from 1890 to 1893. This is blocks from my childhood home. He was the first African American to receive a degree from Harvard.

Robert Frost lived at 35 Brewster Street. Frost, who attended high school in Lawrence, Massachusetts, lived in the West Cambridge home from 1943 to 1963.

T.S. Eliot lived at 16 Ash Street.

E.E. Cummings lived at 104 Irving Street. He was an innovator. He also wrote a poem about “Cambridge Women”. He lived at the Irving Street home from 1892 until about 1917.

Also you can find homes of the genius Nabokov and the great and beloved Julia Childs if you look around.  



The Friend, based on a true story and Matthew Teague’s autobiographical essay.

As Dad in Light of My Life, which he also wrote and directed.


The World to Come from his own production company Sea Change.


As Lee Chandler in Kenneth Lonergan’s Oscar winning Manchester by the Sea.

As Robert Ford in Andrew Dominick’s Oscar nominated The Assassination of Jesse James by the Coward Robert Ford.

As Russel in Gus Van Sant’s To Die For and and as Morgan in Van Sant’s Oscar winning Good Will Hunting.

As Rodney Baze Jr. in Scott Cooper’s Out of the Furnace.

As Patrick Kenzie in Ben Affleck’s Oscar nominated Gone Baby Gone.