How To Have A Great Boston Summer

June 28, 2013

I was born and raised in Arlington, MA. When I got to college I just told people I was from Boston — “twenty minutes outside of Boston,” I’d say. I soon learned that EVERYONE from Massachusetts said that, but it was true! My parents’ house is a 5-minute drive from the Alewife T station, which’ll get you to Park St. on the Red Line in fifteen minutes. I’m from Boston.

Since college, I’ve been back and all around, living in Arlington, Allston, Brighton, and Cambridge. It was really cool to come back here as an adult and re-discover the city this way – when I was a kid, I had no idea how lucky I was.

Next week, I’m moving from Boston to NYC. What! I’m super excited, but also so sad. All I have to do is drive down Memorial Drive, past the Charles and the flowering trees, and I’m filled with wonder at and love for this city. Boston is small enough to feel really comfortable, but it’s full of neighborhoods to explore. Like a pop-up book, Boston is wonder contained.

I will miss Boston this summer. If you’re going to be there, here are the things you should do.

SOWA market


SOWA market is open every Sunday, May through October, from 10-4. Located in the South End, it’s a marketplace that features arts and crafts vendors, millions of food trucks, and a farmer’s market. It’s the perfect place to go after an awesome and/or rough evening – you can walk your emotions around in the sun, feed them, and buy them things. I offer this as an alternative to Sunday brunch.

Jamaica Pond


Jamaica Plain is a little oasis of a place. JP’s biggest problem is accessibility – you have to either drive there or take the Orange Line (and, if you’ve spent any time in Boston, you probably don’t feel awesome about the prospect of the Orange Line). Once you get there, though, you’re in a whole new world. Parking is ample and doesn’t require a resident sticker. Streets are quiet and adorable. And then, there’s the pond.

Jamaica Pond is beautiful, and easy to walk to from anywhere in JP. Grab a sandwich at City Feed and head down there – you can eat half the sandwich sitting on the dock, walk 1.5 miles around the pond, and enjoy the other half from the same spot. Perfect day.

First Fridays at the ICA


Boston’s Institute of Contemporary Art is a really sweet place, and it becomes even sweeter in the summer. On the first Friday of every month (June, July, and August), the ICA hosts a party that includes DJs, live performances, gallery talks, and good food and drinks. It’s museum-inspired nightlife!

Castle Island


If you’re not spending the day at Jamaica Pond, you should spend it at Castle Island. Castle Island is in Southie, on the shore of the Harbor. What is it, you ask? Well, it’s not REALLY an island – it’s connected to the mainland by causeways — and there aren’t REALLY castles on it. But it does have Fort Independence, which is a fort, and more importantly, it has Sully’s.

Go to Sully’s and get a hot dog, or a fricken burger, or a lobster roll – you won’t be disappointed. Dip your fries in ketchup as you sit on the grass and look out on the water and gossip about the weekend’s events. You’ll be surrounded by people doing just that, and you’ll be satisfied, and you’ll be happy.

(Just to note: Sully’s is technically called “Sullivan’s,” but here in Boston we always shorten Sullivan to Sully. See: any kid with the last name Sullivan who was referred to as “Sully” in high school.)

The Hatch Shell


Back in the days of Oldies 103.3, the Hatch Shell featured summer concerts sponsored by that rockin radio station, and I once saw The Temptations play there (I was tipsy, I danced along to “Just My Imagination,” it was amazing). Oldies 103.3 is now a thing of the past, and I’m sad to see that there aren’t any good concerts at the Hatch Shell this summer. I’m heartened, though, that there ARE a bunch of great movies. These movies are family-oriented; but who doesn’t want to see “Wreck it Ralph”?

The movies happen on Friday nights, and you can bring a blanket and a picnic. When the movie’s over, you’re right where you need to be to hit the town — plus, you’ve just seen a great animated film, so you’re ready to party.

Memorial Drive


I mentioned Memorial Drive in my intro because it’s just so pretty. On a nice day, it’s a stretch of road that feels truly epic – all along Memorial, there are great places to sit by the water, or take a long walk, or go for a run or a bike ride. On Sundays in the summer, it’s even better – from the last Sunday in April through the second Sunday of November, Memorial Drive is closed to car traffic for the day. While this is a huge pain if you’re driving, it’s great if you’re not; the street is yours! Head down there on a nice Sunday and do whatever the hell you want.

Drinks on Patios


Drinks on patios are goddamn great. They are second only to drinks on roof decks (SEE BELOW) in the race for best summer thing ever. Boston, in its glory, supplies some excellent patios for summer drinking in the day and night. Here are three:

1. The Draft

The Draft is located in the heart of Allston, so if you’re 21-24, this is a great spot for you. You’ll find lots of your peers here, and they’ll range in style from hipster to jock, as The Draft is a dedicated sports bar located in hipster town. It’s an interesting mix.

Head to the back and turn right – out here, it’s a party. The Draft patio has its own bar, tables with umbrellas, and full food service. People are having a good time on The Draft patio; oh yes they are.

2. The Ashmont Grill

The Ashmont Grill is located in Dorchester, shockingly close the Ashmont station. I say shockingly because once you’re there, it feels vaguely foreign. The patio is fenced in, making it secluded, comfortable, and romantic. It’s lit with fire lanterns — oooh. The food is delicious (though not cheap — you’re not at the Draft, guys). It’s real nice.

3. Charlie’s Beer Garden

There’s something special about Charlie’s. It’s smack in the middle of Harvard Square, and there are lots of classier places around it, but it doesn’t succumb to the snobbishness. The menu is gigantic and entirely decent (not great, but decent – as it should be), and the atmosphere is friendly and convivial. In the winter, it’s somehow still worth it to go even though it’s so crowded that it often requires doing major table stakeouts. But in the summer? Heaven.

It’s heaven because of the Beer Garden. Walk down the small alley to the left of the restaurant and you’ll find yourself in a garden paradise, with its own bar, access to its own bathrooms (crucial), and a feeling of seclusion deep in the middle of the square. It’s generally full of friends, and it’s a great place to linger as the night gets dark. I celebrated my 23rd and 24th years at Charlie’s, and I’ll be heading there for my going away party. It feels like home.

Drinks on Roof Decks


Alright, now that we’ve talked about patios, let’s get to the really, really good stuff: ROOF DECKS. Obviously, nothing in the world is better than a roof deck in the summer, and Boston roof decks in particular are a special kind of great. The city is small enough that, on the right roof deck with the right sky, it can feel like we’re all on a roof deck together. Here are three of the best ones:

1. Revere Hotel Rooftop

This is a newly opened, fancy roof deck. It’s not cheap, but for your money you get to sit in comfy armchairs, sip fancy drinks, and look out at the sky. This is a splurge roof deck, which everyone needs once in a while.

2. Rattlesnake

Rattlesnake is the perfect after-work roof deck, if you work downtown or even if you just pretend that you do. It’s right on Boylston, and it’s for sure a downtown bar – i.e., the crowd can get pretty bro-y. Depending on your preferences, you can either relish the bros or ignore them and just focus on where you are: it’s beautiful, and has a really intimate feel amidst the vast sky.

3. Daedalus

Yes, I did save the best for last. Daedalus is in Harvard Square, and it tends to attract a slightly older crowd (by slightly older, I mean late twenties and early thirties. WE’RE ALL YOUNG). Just walk by the restaurant and look up, and you’ll immediately wish you were on that roof deck — Cambridge, surrounding the restaurant, feels quaint, and the deck feels somehow historic. Get some drinks here, and you’ll feel entirely in love.

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