Summer in the City

The insider’s playbook to summering in Boston like a pro, from the hottest rooftop pools to the best festivals.

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The Sinclair, in Harvard Square, is just one place to sip and dine al fresco this summer. (See #9.) / Photograph by Mike Pecci, wardrobe styling by Tesstylist, prop styling by Jennifer Dunlea, hair by Yojanse Jimenez/Team, makeup by Vicky Maryelle O’Rourke/Team.



Stow the beer goggles and view the world (including your prospects) through rosé-colored glasses, easily the season’s most refreshing accessory. As U.S. quaffers learn the joys of post–white zin pink, Old World producers have grudgingly stopped withholding their blushing best—and local sommeliers have been hoarding the good stuff (meaning, they’d appreciate the help).



Our deliberately abridged (and blatantly borrowed) guide to where our al fresco dining tastes fall this summer, from waffle fries in paradise to foie gras in an alley—and every permutation in between. —Jolyon Helterman and Leah Mennies


Click to view larger. / Photographs by Toan Trinh

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Book Photo via Shutterstock



We asked local luminaries to help us compile the perfect summer reading list.

Doris Kearns Goodwin, Historian
King and Maxwell, by David Baldacci

“In the last few years I have fallen in love with mysteries,” says the Pulitzer-winning biographer.

Tom Perrotta, Novelist
The Black-Eyed Blonde, by Benjamin Black

“I’m usually against this sort of homage,” Perrotta says about this revival of Raymond Chandler’s famous private eye, Philip Marlowe. “But I’m a longtime fan of Chandler, and Black is my current favorite crime writer, so I’m willing to make an exception.”

Mary Fuller, Professor
The Chanur Series, by C. J. Cherryh

The head of MIT’s literature department says her favorite summer books are in the realm of science fiction. “I like serial fiction by authors who build interesting, complex worlds,” she says. “I love almost everything by C. J. Cherryh.”

Jasper White, Chef
The Perfectionist: Life and Death in Haute Cuisine, by Rudolph Chelminski

“The story does give great insight into the incredible pressure of being a chef on the big stage—what makes many of us tick,” says the chef-owner of Summer Shack.

Jack Williams, News Anchor
Goodbye to a River, by John Graves

“Written more than 50 years ago, it remains one of the most beautiful books on preserving what we have before it is gone forever.”

Jim Braude, Radio/TV Personality
How About Never—Is Never Good for You? My Life in Cartoons, by Bob Mankoff

“As weird as it feels, there’s nothing quite like being alone and laughing out loud,” Braude says of this retrospective of New Yorker cartoons. “Decades of one-panels can do it for you.”

Amy Ryan, Powerhouse Librarian
Where’d You Go, Bernadette? by Maria Semple

“I am drawn to coming-of-age stories, and this one is as moving as To Kill a Mockingbird,” says the president of the Boston Public Library. —Samantha Pickette

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Four pretty-solid-if-you-think-about-it fresh-air alternatives for the sun-seeking sports spectator.

Charlie’s Kitchen

Ever watch a hockey game with a budding hipster? Exactly. Even when this Harvard Square hangout gets crowded, not everyone’s massed around the TVs in the open-air garden, meaning plenty of prime space for you and your brew. Which is actually one perk of hanging with this particular crowd: They drink better beer.


Legal Sea Foods, Harvard Square

Stationed in the courtyard of the Charles Hotel, this outdoor bar—complete with a full ring of flat-screens—offers some of the best people-watching in the Square. So even if the game’s a blowout, at least you can look away. See that dude on the make at that corner table? Yup, he’s not scoring either.


The Baseball Tavern

Is it counterintuitive to hit a bar in the belly of the beast? Absolutely. But therein lies the beauty: If everybody’s inside the stadium, there’ll be room for you on this roof deck overlooking Fenway Park. Bonus: You can hear the roar of the crowd while you watch on the tube.


Pier 6

Formerly Tavern on the Water, this Charlestown venue is famous for its skyline views—but come on, you know what Boston looks like. Focus instead on the two monster flat-screens with surround sound flanking the granite-topped bar.

617-337-0054, —Jason Schwartz



A 183-word valentine to Southwest Corridor Park.

It seems impossible that a 4.7-mile-long, 52-acre green space coursing through the heart of Boston could be a hidden gem, and yet Southwest Corridor Park remains one of the city’s great unheralded treasures. There’s nothing like riding your bike through the havoc of the city’s streets, making that hard turn onto the corridor, and suddenly finding yourself alone, riding down a pleasant, tree-lined path without any fear of getting maimed or run over: If urban Zen exists in Boston, this is it. Built along the Orange Line on land once intended for a highway, the corridor starts beside Back Bay station with a series of picture-perfect garden spaces. From there, it continues as a path—opening up into a full park at every T stop—all the way down to Forest Hills. It’s a bit like New York’s famed High Line, except, you know, actually useful. (For that, you can thank the seven basketball courts, five tennis courts, two street-hockey rinks, two amphitheaters, and, yes, 11 tot lots.) So let the tourists have the Freedom Trail; this is the only path we need. —Jason Schwartz

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If you like plush cabanas and mind-blowing Back Bay views, the Revere’s new rooftop pool bar has you covered. / Photograph by Mike Pecci, wardrobe styling by Tesstylist, prop styling by Jennifer Dunlea, hair by Liz Grace/Shag, makeup by Vicky Vasvatekis/Shag.



A splash-by-splash guide to urban swimming holes.

Rooftop at Revere

Seven stories above the Theater District, an international crowd mixes with locals unwinding in chaise lounges and ogling the skyline. Minor quibble: Technically speaking, the pool is indoors. But an adjoining 16,000-square-foot terrace makes this al fresco “rooftop” a worthy place to swim, sun, and sip—and jiggle: See the menu of “Classy Jello Shots.”

Tips: A $20 fee applies to non–hotel guests Monday to Friday ($30 on weekends), but anyone over 21 is welcome free of charge after 5 p.m.


Gold Star Pool

Cambridge’s only city-owned outdoor pool may lack swank, but you’ll forget all about creature comforts after a few cannonballs in the deep (9-foot) end. Families and progressive urbanites gather to escape summer’s swelter in the unheated municipal waters and bask in the price of admission (75 cents).

Tips: BYO lounge chair, drinks, and snacks. The pool stays open past 5 p.m., so aim for the end of the day for a revitalizing, whine-free dip after the kiddies have toddled home.


The Colonnade

At 11 breezy stories high, this is Boston’s only open-to-the-public rooftop pool (pictured below)—or RTP, in the parlance of those who say “SoWa” unironically. The daytime mellow of lounging hotel guests and professionals playing hooky gives way to a lively après-work-cocktail crowd. The scene-y oasis debuts a sophisticated redesign this summer.

Tips: The pool stays open until midnight Friday through Monday. Skip the daily $40 entrance fee for non-guests and kick back gratis on weekdays, 5 p.m. to 7 p.m.

617-425-3408, —Margaret Heidenry

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Not to knock those chintzy webbed-polypropylene numbers, which make excellent post-snowstorm place savers for certain adult vandals. But if it’s your posterior you’re looking to park—at an outdoor concert in Lenox, say, or some pyrotechnic celebration—this slick folding chair by Flux ($149) lets lawn loungers (weighing 350 pounds or less) take a load off in sweet, minimalist style.

617-942-7425, —Jolyon Helterman