Summer in the City

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

Edited by Jolyon Helterman

With all due respect, kicking back come summertime has never been our forte. The instant the sun deigns to show its face, we somehow drop our A-game. We sweat profusely. We pile into crowded landmarks and ersatz eateries like Fodor’s-thumping newbies. To that end, we sleuthed out Boston’s best rooftop pools, festivals, hang-gliding cliffs, pitcher cocktails, mini-golf meccas, urban beaches, outdoor dining rooms, bespoke picnic baskets, and tons more for this, our insider’s guide to falling in love with this town when it’s not cloaked in white. Hey, see that funny bright light streaming down from the sky? You’re just gonna love it.

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Sun-snack in style with a bespoke picnic basket from Central Bottle. (See #2.) / Photograph by Mike Pecci, wardrobe styling by Tesstylist, prop styling by Jennifer Dunlea, hair by Liz Grace/Shag, makeup by Vicky Vasvatekis/Shag.



Because schlepping off to some far-flung plot of coastline is strictly for the landlocked.

Carson Beach

With tons of new sand and brilliant downtown views, Carson Beach (pictured) is arguably both the city-est and the beachiest of Boston’s city beaches. The bathhouse has new showers and changing rooms, and the old-school bocce courts and chess tables bump up the nostalgia quotient. Peckish after a swim? The South Boston location of Tasty Burger makes beach deliveries. | Public toiletslifeguard on dutyfree parkingMBTA accessibilitygood for babe-watchinggood for sandcastle-buildingplenty of shady spots.

Castle Island/Pleasure Bay

Actually part of the mainland, Castle Island is home to Fort Independence, which is listed on the National Register of Historic Places, and to the beloved hot-dog shack Sullivan’s, which ought to be. The grassy park surrounding the fort is one of the city’s best kite-flying and picnicking spots, and adjacent Pleasure Bay Beach boasts clean sand and a calm lagoon. No wonder Whitey Bulger loved hanging out here. | Public toiletslifeguard on dutyfree parkingMBTA accessibilitygood for bird-watching, plenty of shady spotstouristy enough.

The Charles River Esplanade

The erstwhile dirty water off the banks of this riverside park is now swimmable. Well, on special occasions, anyway. On July 12 and July 26, three local organizations will cohost the second annual Charles River Community Swims, allowing 30 people at a time, for 30 minutes at a time, to brave the caramel-hued surf off the dock near the Hatch Shell. | Public toiletslifeguard on duty, MBTA accessibility, good for babe-watching, touristy enough.

Spectacle Island

So what if this 105-acre Boston Harbor Island was once the site of a horse-rendering plant and a city dump? It sure cleaned up nice! Accessible by ferry (from Long Wharf) from May through October, modern-day Spectacle offers 5 miles
of walking trails and two sandy beaches. | Public toiletslifeguard on duty, good for bird-watchingplenty of shady spotstouristy enough.

Yirrell Beach

Per the surfer’s code, we’re not supposed to talk about Winthrop Jetty, the über-secret local surfing spot that produces surprisingly respectable waves, especially during hurricane season. So instead we’ll tell you about the adjacent town beach, which boasts family-friendly shallows for swimming, an annual sandcastle contest, and nail-bitingly close-up views of planes landing at Logan. | Free parkingMBTA accessibility, good for sandcastle-building. —Carmen Nobel

— Key 

Public toilets (the ocean doesn’t count!)
Lifeguard on duty
Free parking
MBTA accessibility
Good for bird-watching
Good for babe-watching
Good for sandcastle-building
Plenty of shady spots
Touristy enough to take out-of-town visitors


Central Bottle Picnic Basket / Photo Provided



Yes, scarfing down Quiznos while squatting in the dirt is, technically speaking, a picnic. Here are three easy upgrades.

Central Bottle

What you get: A wicker basket for two ($75) loaded with saucisson sec, an Iggy’s baguette, cheeses, house-made fig jam, olives, a Mast Brothers chocolate bar, bottled water, and beer or vino.

Thoughtful extras: Cloth napkins, a corkscrew, a cheese knife, a cutting board, wineglasses, plates, and silverware.

Head for the …benches, facing the water at Lechmere Canal Park, a six-minute drive from the shop.


Beacon Hill Bistro

What you get: With an hour’s notice, lunch (weekdays) or dinner can be packed into a basket at no extra charge. While the entire menu is your oyster (literally: shucked bivalves are $3 each), items like duck-liver mousse ($8) and crab roll with fries ($15) whisper “al fresco portability” more than French onion soup ($8). But it’s your picnic.

Thoughtful extras: A blanket.

Head for the …willow trees, two blocks away in the Public Garden.


Boston Cheese Cellar

What you get: The Roslindale shop packs a brown paper bag with a traditional ploughman’s lunch, including two cheeses, either local apple chutney or pepper jelly, grapes, a partial baguette, and sweet pickles, all for $6.95.

Thoughtful extras: Lunch. For seven bucks.

Head for the …headstones, at nearby Forest Hills Cemetery, where you can toast the likes of poet e.e. cummings.

617-325-2500,—Raquel Kaplan


Photograph by Toan Trinh



Two editors make dueling cases for the ultimate mini-golf haven: history vs. aesthetics.

Golf on the Village Green

This is mini golf as our founding fathers ­intended it: patriotic and kitschy, with a tinny fife-and-drum soundtrack. Themed holes like “Faneuil Hall” and “Old North Church” don’t just challenge you athletically, they force you to grapple with the same tough choices Revolutionary generals faced (attack from the left? the right? gently up the center?). The militia of replica minutemen standing sentry only adds to the nationalistic splendor. Of course, this Natick institution isn’t perfect; it’s like America, with all its warts. And I’m pretty sure that’s exactly how Revere, Adams, and Washington—by legend, ace mini golfers themselves—would want it.

508-653-4671,—Jason Schwartz

Route 1 Miniature Golf & Batting Cages

New England Journal of Aesthetic Research founder Greg Cook has been critical of the state of public art in Boston. But he is unequivocal about the giant orange dinosaur that menaces the sixth hole at this Saugus landmark (pictured). Looming over a bend in Route 1, the T. rex is a standout on a strip that boasts some of America’s gauchest roadside architecture. And it’s also art—even if not often acknowledged as such. “Boring art-world snobs somehow can’t see giant sculptures if they aren’t ‘officially’ done by MFA-degreed insiders,” Cook says. True dat. Of all the beasts, the green ­diplodocus on four might be the toughest putt. Still, nothing compares to staring down the big orange guy.

781-233-2811,—Carly Carioli

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Painting Photo via Shutterstock


BE A _____ FOR A DAY.

Discover a hidden talent—or rule one out—with a strategically chosen in-town (or close enough) activity.


The Beacon Hill outpost of Savenor’s market offers hands-on butchery classes ($200) with a veritable Noah’s ark of meaty beasts.



Turn their polite chuckles into gut-busting guffaws at ImprovBoston’s beginner-­friendly workshops ($10), held most Sunday ­afternoons.



Put in a solid one-eighth-day’s work at Brigham Hill Community Farm, in North Grafton, where you can reap the ­harvest, help the needy, and still catch the tail end of brunch. Volunteer drop-ins are welcome Monday to Saturday, 9 a.m. to noon.

774-551-6544, ­

Racecar Driver

Step up your car-pooling game by mastering the high-speed curves at Thompson Speedway Motorsports Park’s High Performance Driving School ($1,500), in Thompson, Connecticut. Upon successful completion, advanced students may be invited to tackle the Leverett Circle Connector.


Tango Dancer

The Tango Society of Boston offers free monthly moonlit lessons on the John W. Weeks Bridge spanning the Charles. Rose to clench between teeth sold separately.


Movie Star

Ready for your ­close-up? How about your far-­corner-of-the-frame Person Milling Around cameo? Sign up for Boston Casting’s extras stable and, with any luck, you’ll end up photo-bombing Black Mass, the Whitey Bulger biopic shooting this summer.


Glass Blower

Put the season’s hot air to good use by pursing your lips in pursuit of transparent artistry at a Diablo Glass School workshop, in Mission Hill.



Fly with the (legally protected bald) eagles during a hang-gliding tutorial at Morningside flight park, in Charlestown, New Hampshire. Four-hour intro courses start at $175.



Drop down your beats better after the gratis lesson that comes with a studio tour of Mmmmaven’s DJ and music-production school, in Cambridge. These are skills that, given the right dance-floor situation, might just save someone’s life.


Landscape Painter

Grab a palette and join one of the Massachusetts Plein Air Artists’ weekly paint-a-thons, held at local spots so picturesque they make Monet’s beloved Giverny look like a toxic landfill (more or less).—Margaret Heidenry

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Oysters Photo via Shutterstock



Enjoy Friday tours (1 p.m. and 3 p.m., $20) of Island Creek’s oyster beds and sorting facilities aboard a skiff off Duxbury. The excursion culminates in an on-the-half-shell tasting. 781-934-2028,

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Preserves Photo via Shutterstock



The League of Urban Canners will prune and harvest your fruit trees and arbors free of charge and give back 10 percent in the form of yummy preserves. (They keep the rest.)

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Lobster Roll Photo via Shutterstock



If you like…

Handmade baubles and hybrids → Coolidge Corner Arts Festival (Free, 6/7,

Deviled tea eggs and diesel → Somerville Food Truck Festival ($5, 6/7, Assembly Row,

Passed bites and perky patellas → Chefs in Shorts ($80, 6/20, Seaport,

Steel drums and stuffed roti → Boston JerkFest (Starting at $12, 6/28, South End,

Paul Revere and pennywhistles → Boston Harborfest (7/2–7/6,

IPAs and ironic facial hair → WGBH Craft Beer Festival (Starting at $40, 7/12, Brighton,

DIY and dance troupes → Artbeat (7/18–7/19, Davis Square,

Lobsters and “lobsters”* → Boston Seafood Festival (7/27, Seaport,

Cosplay and Captain America → Boston Comic Con (Starting at $20, 8/8–8/10, Seaport,

Dumplings and dancing dragons → August Moon Festival (Free, 8/10, Chinatown,

Eco-friendliness and earnest facial hair → Boston GreenFest (8/15–8/17, City Hall Plaza,

Pepperoni pizza and processionals → Saint Anthony’s Feast (Free, 8/29–8/31, North End, —Abby Ringiewicz

*Humans dressed up to look like lobsters; non-edible.