Meet the City: Boston

Among U.S. cities, Boston stands apart for its place in the country's history. A significant chunk of the 16 million visitors the city counted in 2014 come to walk the historic Freedom Trail, watch a game at Major League Baseball's oldest park, and soak up some red-brick architecture. 

But to stay in the past would be a mistake. Young people aged 20 to 34 make up more than a third of Bostonians, giving this city the highest proportion of young adults of any major American city.  They keep one of America’s oldest cities young. The city’s roster of food trucks seems to expand by week, offering gluten-free chimichurri tempeh tacos and cheddar and egg sandwiches stuffed into scallion pancakes. A long-time tech hub anchored by major universities, Boston and Cambridge continue to attract young people with an exciting startup scene that leans more toward game-changing technology and services than Uber-for-X. 

The city’s charm is its mix of old and new, making Boston one of the few American cities where it feels like daily life takes place in a history textbook. That might be why locals love to send visitors to the North End, the oldest residential neighborhood in the city. Here, a stroll from your apartment to the nearest coffee shop might take you past Paul Revere’s house—as well as a few dozen excellent Italian restaurants.

My favorite views in Boston are always straight up. Look up and you'll find layers of history: pre-Revolutionary War church spires in the foreground, brutalist concrete and '80s blue glass towers battling it out in the background. And all around, tower cranes in the periphery, constructing the next generation of Boston high-rise apartments and hotels.

---

I recommend...

GO

---

The whole New England "leaf peeping" thing is for real. If you visit in the fall, take a drive up to the coast of Maine.

watch

---

Spotlight (2015)

The Departed (2006)

Good Will Hunting (1997)

Love Story (1970)

DO

---

Picnic on one of the docks on the Charles River Esplanade 

Go to a baseball game at Fenway Park

Get lost in the little streets of Beacon Hill

---

The City Guides You'll Meet

Walk Sandy's "Boston Loop," starting with brunch in the South End--a Boston weekend staple.

Take a tour of MIT with Alina and discover hidden works of art on the brainy Cambridge campus.

Eat Vito's favorite breakfast sandwiches in Boston's smallest neighborhood, Bay Village.

Stock up on picnic essentials with Jingying as you explore the North End, and find out where Boston's "basement wonder bakery" is.

Say hello to Indigo at a dog treat emporium on one of the South End's most charming streets.

Play Buck Hunter with Joey all around Boston, including at a classic Boston dive bar once described as "a scene straight out of Star Wars."

Do the first half of the Freedom Trail with Emily, but not the second, which she thinks is boring.

Sail on the Charles River with Monica with Community Boating, America's "oldest, continuously running public sailing center."

The Boston Loop with Sandy

Get brunch in the South End, or go to the SoWa for food trucks. For brunch in the South End, Coppa is delicious, but super super expensive for what it is. I really like Metropolis for brunch. If you want to do a not-cheap-but-cheaper coffee and breakfast sandwich, you could go to Render on Columbus and Mass Ave.

Then just walk around! Seriously.

Before winter sets in, the Tuesday and Friday farmer's market at Copley Square offers a bounty of local produce. In the fall, expect outrageous quantities of apples, cider, and cider donuts.

First, go to Copley Square and walk around there.

Then walk down Newbury, and you could make a stop at the Thinking Cup for coffee or a pastry or sandwich.

From Newbury, where there are a lot of shops, walk over to the Esplanade along the Charles. There's an access point on the Mass Ave. bridge.

Walk down the Esplanade to Beacon Hill.

Walk through Beacon Hill to Boston Common.

Maybe end in the North End and get dinner there.

The Tour de Cambridge with Alina

Do the Cambridge walkabout. Or the Tour de Cambridge. Whatever you want to call it. You can basically just start in Cambridge and walk toward Boston. By the way, Cambridge is unofficially known as “The People’s Republic of Cambridge,” and its people are “Cantabrigians.”

Toscanini's is worth lining up for. And on hot summer nights, expect a line.

I would suggest starting the tour in Harvard Square. Hang out around there, go to the river, and then keep going down Massachusetts Ave. toward Central Square. Do ice cream at Toscanini’s. Go to the MIT museum, if you want to. Wander through the MIT campus and buildings.

Here’s what I recommend for MIT. Walk down Mass Ave. to 77 Mass Ave, the main entrance of MIT. You absolutely cannot miss it, it’s the one with the huge columns.

If you have lots of appetite to explore, cross the street and check out the chapel, a cylindrical building with no windows and a moat, and Kresge auditorium, a large windowed building across the green from the chapel. Both were designed by Eero Saarinen, and are pretty cool examples of mid-century modern architecture, which is a thing people like. Kresge is a perfect 1/8th of a sphere!

But if you have not a lot of appetite to explore, then skip the street-crossing and go straight inside 77 Mass Ave, and walk down the infinite corridor. Stay on the right side of the hallway, and don’t block the flow of traffic! Seriously, it’s the worst. In the middle is Building 10, which is right under the Great Dome, and has a great view out over Killian Court. Many people take pictures here, and if you do, go outside and check out the scientists inscribed on the stones surrounding the court. On the 5th floor of Building 10 is Barker Library, which is right under the dome and pretty cool. Also home to many studying—and sleeping—students.

The absolute can’t-miss at MIT is the Sol Lewitt public atrium art. It’s this huge mural thing that’s the floor of an infill building, which is a building built between two existing ones. The whole thing feels like some optical illusion/Escher painting. Because the inside of the building is the outside of two others, there are these bridges across, and the floor is colorful and bright. So from every perspective, you see something unexpected. 

End up at Area 4, for beer, pizza, and lawn games.

Here’s a detour you could take. From Harvard Square, take the bus—it’s super easy, and they take cash, and you can track it on a variety of apps—to Mt. Auburn Cemetery and Sofra. Mt. Auburn, because it is absolutely beautiful, and Sofra, because everything is delicious.

---

You must try B3 (Brown butter, brown sugar, and brownies) at Tosci’s. This is the only right answer for favorite flavor. Even if you occasionally enjoy other flavors, like burnt caramel or nocciola/cocoa pudding combo. You can try several flavors, so definitely don’t make any hasty decisions…But then choose B3.

Breakfast sandwiches in Bay Village with Vito

Tiny Bay Village might be Boston's most charming neighborhood. Stepping into its streets feels like entering a different time period and place. But like Beacon Hill, Bay Village and its brightly painted doors are classic Boston.

Some of the best breakfast sandwiches are at Mike and Patty’s, in Bay Village. The Fancy is their staple. Bacon, egg, cheese, avocado, on multigrain Iggy’s Bread. Some great sauces. Sage and Ron run the counter there. So my typical morning on a weekend is to wake up and get a Mike and Patty’s sandwich.

Then I go over to MMMMaven, an events company that puts on electronic dance events, for my DJ class. They also have free workshops and organize the Thursday night at Middlesex, and bring deep house acts to town. That’s one of the most consistent dance nights in Boston.

Also on Thursdays—every third Thursday of the month, the Isabella Stewart Gardner museum has a mixer event in the atrium, which is like the classiest thing ever.

Italian picnic on the Greenway with Jingying

"Basement wonder bakery" Bricco, where the $6 prosciutto parmigiana loaf will be handed to you piping hot. This hefty meat and cheese-stuffed ciabatta will change the way you think about bread.

Start at Boston Public Market with iced coffee and Union Square Donuts. The vegan ones are so good. I’m not vegan, but the coconut oil adds this chewiness and texture that is really appealing.

Then walk down the greenway and admire the art installations. Maybe even take a ride on the carousel, if you’re feeling child-like.

You can pick up picnic ingredients in the North End to eat on the greenway with the sun shining on your face. Get salamis, cheeses, and olives from the Salumeria on Richmond St. and bread from the basement wonder bakery, Bricco.

On the other hand, if you’re feeling too lazy to assemble any foods, grab an Italian sandwich with everything--everything--from Monica’s on Salem, and if you have a companion, also get the steak bomb from Dino’s across the way. The steak bomb tastes like a much nicer version of a McDonald’s cheeseburger, in the best way possible.

Then walk toward the aquarium, and continue down the harborwalk. You can walk all the way to the ICA. And on the way back, you can stop for a lobster roll. There’s this one place called like, “Amazing Fresh Lobster,” or something just really straightforward like “This is Fresh Lobster.” 

Then go to the Lawn on D, and have some stuff from the food trucks. Sheherazad is the best food truck in Boston. There is cinnamon in the hummus! 

Then walk off your snack along the Charles River. Walking along the Charles isn't the most convenient thing, but you know, at this point you've eaten like four meals, so I think you can deal with it.

Then I’d go to Picco for ice cream, because I just love Picco. Mint chocolate chip ice cream, and dark chocolate sorbet. I insist on the sorbet. I insist.

---

I think people like visiting Boston because

1. It's pretty

2. It's quaint

3. It's historic. Honestly, I feel conflicted about this one because one can only call Boston historic by American standards.

4. Universities

---

There are giant brains quietly humming together to pull the leading edge of humanity hurtling into the future. If you spend enough time in Cambridge, you start to see and hear that everywhere.

Not in the disrupting industries with technology way of SF. Not in theWe Are Living In Blade Runner way of large Asian cities. In the, this stuff will save our lives without us realizing it for the next century way that is only happening in enclaves of scientific progress.

Also, the summers are pretty nice.

A stroll down Shawmut with Indigo

I work at Polkadog, a self-proclaimed treat boutique for dogs. We make everything that sits on the counter, and everything else in the store comes from all over the world. From every continent except Antarctica. We may have the biggest selection of dog treats, snacks, delicacies…I mean, variety is the spice of life.

The South End--specifically Shawmut Street--is just a great neighborhood to hang out in.

This charming residential block of Shawmut Street is packed with local go-tos. It's where South Enders pick up dinner party supplies, brunch on Saturdays, and walk their dogs.

Formaggio Kitchen down the street is a renowned cheese maven place. That's my favorite.

And Myers and Chang is also the bomb.com.  SoWa Market is going on nearby, and it’s bigger and better than ever, with a ton of food trucks, art, and vintage stuff. Then there’s Old Japan. It’s this store that has products from Japan and they have the biggest maneki-neko collection.

They also do garden tours here, because the South End has a lot of well-kept, famous gardens. There are also architecture tours that show the historical buildings. 

Once you’ve explored Shawmut, I’d stop at the Buttery and make a right toward Tremont.

Dive Bar Buck Hunter Tour with Joey

My absolute favorite place in the whole world is the Tip Tap Room in Beacon Hill. Definitely get one of the burgers. According to the waitstaff, the steak tips are the most frequent order, but that’s just beef shaped into little triangles. The burger, you get the same amount of meat, but with amazing sauces and things. So that is where I would start the Buck Hunter Tour. Tip Tap doesn’t have Buck Hunter, just to be clear. I just think it’s amazing, in general.

Good luck trying to weave your way to the bar on the weekends, but Beacon Hill Pub is empty during the week--perfect for a few uninterrupted Buck Hunter games and a cold Harpoon IPA. A cheeky review behind the bar describes the BHP as "a bar scene straight out of Star Wars."

So to do the Buck Hunter tour, you just go around to different bars and play Buck Hunter. I mean, you would be with a friend. You could do it yourself, but…that would be a different experience.

So there are a few different places you can go. There’s the classic, BHP. Beacon Hill Pub. And the Red Hat, which is next door to the Tip Tap Room. 

But the best Buck Hunter place I’ve been to is Jillian’s, at Lucky Strike. You know, the bowling place? They have all the Buck Hunters. Buck Hunter Safari, Buck Hunter HD, there’s one that’s like connected to the Internet, and like, Super Big Buck Hunter Pro HD something. I mean, just a whole chain of adjectives.

---

I just moved to Cambridge and my go-to bar here is definitely People's Republik.  It's a dive bar with cheap beer and three dartboards, but is actually pretty cleaned up with lots of space for hanging out.  Dive bars are great, but sometimes they can feel like getting stuffed into a smelly closet.

I think Southie has a bunch of interesting bars for drinks.  There's a super dive bar, Lucky's, right next to the fancy, probably-has-a-line-but-not-actually-crowded cocktail bar Drink. Drink is a great place for visitors, but I never end up going there myself because it's so far.

---

I think a typical night out involves wandering around a series of bars, constantly trying to remember where you know that guy you just ran into from.

Boston on foot with Emily

One of the coolest things about Boston is that everything is walkable. Not to shit on the T, but you could do the entire day on foot. And there aren’t that many cities like that.

Do the first half of the Freedom Trail, but not the second, because like, the density of interesting spots decreases. In the beginning, you can see the Common and the Public Garden and you should definitely do that.

Then halfway, just end in the North End, where you should get a cannoli. Try both Mike’s and Modern Pastry—it’s the scientific way.

A view toward Arlington St. from the Public Garden offers  layers of architecture from different eras

Walk along the Charles. You have to see the Charles. You have to. It’s beautiful. I think it’s beautiful in the winter, beautiful in the summer. It’s what sets Boston apart from other cities. I mean, I’m biased, because I like to run. My favorite part of the Esplanade is, between the Dartmouth St. and Fairfield St. bridges, there’s that area where it splits, and there’s a little section surrounded by water.

Yeah, exactly, Gisele used to Instagram it all the time!

And if you can see a game, go see a game at Fenway. I was raised a Yankees fan, but I still think it’s the most beautiful, just incredible, baseball park in America. 

Boston's neon sunsets are best viewed from the dock on the Charles River Esplanade. They're even better if it's been a cloudy day.

Sailing on the Charles with Monica

I would do three things.

Let's say we're starting in the South End. I would go for a run and run to Cambridge from the South End, down Mass Ave. End up at Life Alive. I usually order the Goddess or the Green Goddess bowl and a Coco Alive smoothie. It’s basically like a healthy version of a piña colada.

Visit this Central Square spot for juices, smoothies, and wholesome bowls with the most delicious, garlicky sauces you (and anyone else you run into that day) will ever have the opportunity to smell.

Then I would walk to the sailing pavilion and sail on the Charles. There are a few different sailing pavilions—for BU, MIT, and then Community Boating, which anyone can do. But basically it’d just be water sports for a few hours. And if you're running or walking, you should definitely do it along the water or the Charles.

Last weekend, I went to a Berklee jazz festival. That was really cool. It happens once a year, but Berklee has a lot of concerts if you sign up for their email list or check out their website.