Everything You Should Eat and Drink around Boston before the Summer Ends

A to-do list of frozen treats, outdoor dining, and more.

Eat outdoors with views at local restaurants like Pier 6 in Charlestown. / Photo by Brian Samuels Photography

Rude of us to suggest that summer is almost over, we know—but our inbox is already filling up with an alarming number of press releases about pumpkin-spice everything, so it’s clear the season’s changing. Below, find our late summer food and beverage to-do list: our favorite Boston-area meals and activities best enjoyed on a warm day when the sun stays out past 7 p.m.

A hand holds a cone with a tall twist of beige and white soft-serve ice cream instead an old-timey grocery store.

Maple and vanilla soft-serve ice cream at Momma’s Grocery & Wine. / Photo by Rachel Leah Blumenthal

Eat Frozen Desserts

We fully believe that all weather is ice cream weather—and we’ve got the Gracie’s Ice Cream hoodie to prove it—but even so, nothing beats a cold cone on a sweltering day. 

  • Try an enormous scoop of black raspberry or Cow Prints ice cream at our 2022 and 2023 Best of Boston winner for ice cream, Crescent Ridge—head out to the original location in Sharon or the convenient kiosk inside Boston Public Market. Find more of our top picks for Boston-area ice cream here.
  • Are you particularly fond of soft serve? Check out our freshly updated roundup here, including a Vermont maple creemee-inspired option right in Cambridge, two spots with soft-serve-stuffed croissants, and even a place to try gold-leaf-covered matcha soft serve.
  • Yep, we’ve got a gelato-specific roundup too. We recommend getting a seat near the open front window at Caffè Paradiso in the North End and ordering the pistachio martini, which comes with a scoop of pistachio gelato.
  • Whether you call them frappes (like a proper Bostonian) or milkshakes, the Boston area has plenty of tasty ice-cream-based drinks. You’ll find us heading out to the tiny Chelsea market La Mesa to enjoy some of the area’s best birria tacos with a decadent churro milkshake for dessert.
  • Discover Greater Boston’s newest ice cream shops among summer’s fresh batch of restaurant openings. You’ll find a cozy new spot in Dorchester with an adorable sloth mascot; ice cream tacos in a downtown food hall; two new outposts of a local vegan dessert chain; the reopening—after a long hiatus—of a Somerville favorite; and Hoodsie-style to-go cups at an Allston restaurant.
A bright red cooler that says Urban Wild is full of a drink topped with watermelon and lemon slices and colorful bendy straws.

Urban Wild’s Afternoon Delight cocktail is one of a couple large-format options, served in a cooler and meant for four to six people. / Photo by Elisabeth Hadjis

Explore Summer’s Most Exciting New Openings (Outdoors!)

There aren’t just new ice cream shops to check out: There are plenty of great restaurants, cafés, and bars that have debuted this summer, too. Here are a few that are already impressing us and boast outdoor spaces worth checking out while the weather cooperates.

  • Drink large-format cocktails out of a cooler at Urban Wild, Charlestown’s new entertainment venue with bowling, live music, and more. An indoor-outdoor lawn area is packed with games like croquet, shuffleboard, and bocce.
  • Speaking of bocce, East Cambridge newcomer Gufo—which recently opened in the old Loyal Nine space—has a lovely outdoor area. Part is covered and part is sunny, with some space for bocce, too. Fuel up for your game with a platter of tasty snacks, like prosciutto with mustard and eggplant caponata with whipped ricotta.
  • Relax over a cup of Turkish coffee while getting in some prime South End people-watching on the patio at delightful new café Sip of Joy.
  • Enjoy frozen cocktails outside at Sloane’s, the new comfort food destination in Allston from the chef and owner of Stillwater.
  • The North End has a new rooftop! Italian steakhouse Umbria debuted this summer, along with its roof deck, Mia.
  • The Smoke Shop BBQ and Mida each expanded to East Boston this season, opening near each other on the waterfront and boasting outdoor seating with stunning views of the downtown skyline. Brisket or pasta—what’re you in the mood for?
  • Pickleball might be the froyo of 2023, but while we’re all still sort of into it, check out the new outdoor courts at Harpoon (while eating pickle-flavored popsicles, of course).
  • Drink natural wine and frozen cocktails outdoors in the heart of Harvard Square while enjoying live music at One Reason Garden Bar. 

Oleana’s patio—still one of the best around. / Photo by Kristin Teig

Actually, Just Eat and Drink Outside Everywhere

It’s fun to check out the newbies, but don’t forget to support your old favorites! 

  • Up, up, and away: Updated for summer 2023, here’s our guide to the Boston area’s best rooftop bars and restaurants, from classics like Felipe’s and Daedalus to recent arrivals like Stratus at View Boston and Mex Taqueria & Bar. Please excuse us while we go enjoy tacos and a mangonada slushie a few flights above Kendall Square under clear blue sky.
  • Ah, beer gardens. Refreshing! Often kid- and dog-friendly, too, if you want to bring along the whole family.
  • Speaking of dogs, you’ve likely been seeing lots more dog-friendly patios and beer gardens in Boston proper this summer since the city now allows businesses to apply for a permit. (Check with your favorite spot directly for details before heading over—not everyone is allowing it.)
  • Eat seafood! This guide includes some of our current fish-filled top picks, from casual to fancy, and a handful of these spots have great outdoor dining spaces—particularly the clam shacks.
  • And here’s a giant list of 60+ of our favorite outdoor dining spots around town, from hidden nooks full of greenery to cozy spots with waterfront views.

Newport Vineyards. / Photo by Annabelle Hendersøn

Go on a Food-Filled New England Road Trip

Late summer is the perfect time to get in a few more weekend trips out of the city. Here are some of our favorite food-filled destinations not too far away. 

  • Portsmouth, New Hampshire: a gin bar, an old-school steakhouse, an acclaimed Mexican destination inside an old Friendly’s
  • Portland, Maine: binchotan grilling, seafood galore, Texas barbecue meets Latin American cuisine
  • Stowe, Vermont: an iconic farm-to-table destination, a burrito-filled base lodge, wood-fired pizza
  • Newport, Rhode Island: hearty brunch with shipyard views, chowder with a side of people-watching, fried clams at a classic shack
  • Charlestown, Rhode Island: Indigenous cuisine from a James Beard award-winning chef, a giant seafood buffet, Red Bull-infused drinks for a caffeinated kick 
Home-cooked steak tips and green beans on a blue plate.

Grill some steak tips in the backyard. / Photo by Rachel Leah Blumenthal

Relax at Home

‘Tis the season for backyard grilling with friends.