The Best Ways to Spend Labor Day in Boston, According to Boston Magazine Staffers

Here’s what to do with your Monday off.

There’s really no need to head for the hills this Labor Day weekend (though if you are escaping Boston, we have some trip ideas). Instead, savor the last moments of summer à la Boston magazine writers and editors, who know how to staycation like nobody else. Ahead, find recommendations from eight staffers on ways to spend the holiday within city limits. ☀️

I don’t care what anyone says, Revere Beach is a Bostonian’s ultimate urban oasis. A 40-ish minute train ride takes you directly to its sandy stretches, where waves crash amongst the ambience of takeoffs, landings, and yo-pros blasting Third Eye Blind from their Bluetooth speakers. Spread out a blanket and join me in spending Labor Day catching rays, sipping on ‘Gansetts, and double-fisting cones from Twist & Shake. And for the record, I’ve never seen needles on the beach. But I HAVE seen sea glass (waiting to be collected), hermit crabs (scuttling coquettishly across the ocean floor), and big ol’ clams (doing whatever clams do). So swim out to the buoys, float on your back, and let the naysayers naysay—it’s pretty hard to hear them with your ears submerged in the Atlantic.

—Alene Bouranova, Editorial Assistant


Photo courtesy of the Revere Hotel

I‘d start the day with a sweet treat at Blackbird Doughnuts (the passion-fruit-glazed is a favorite!), then while away the afternoon sipping cocktails in a cabana on the Revere Hotel’s rooftop and cooling off in the pool. The only choice for dinner? A hot buttered lobster roll at the perennially packed Neptune Oyster in the North End. It’s worth the long wait—as is the Oreo cannoli at Mike’s Pastry. Who says I can’t be a tourist in my own city?

—Brittany Jasnoff, Executive Editor


Photo by Madeline Bilis

Every time I hop on a ferry to the Boston Harbor Islands, I’m always surprised the docks aren’t jam-packed with people. It’s absurdly cool to be able to escape the city with a breezy 45-minute boat ride, and it’s even cooler to hike, swim, and sunbathe on a crowd-free hunk of land so close to home. Though Lovells Island is hands-down my favorite harbor island, it’d be best to spend Labor Day on my second-favorite: Peddocks. It boasts two luxurious amenities that Lovells lacks: restrooms and running water. But really, Peddocks has it all—hiking, swimming, skyline views, military fort ruins, and a colorful history. (Families, Portuguese fishermen, debauching hotel-goers, and Italian prisoners of war all have called Peddocks home at some point.) Start by taking a walk around the perimeter of the island, stopping along the rocky coastline for a swim or two. Feast on a packed lunch, then explore Fort Andrews before kicking back in some colorful Adirondack chairs on the beach.

—Madeline Bilis, Associate Editor


Allium toasts / Photo by Dominic Perri

For a Labor Day spent in content, (which these days means out of the path of tourists), I’d head to Coolidge Corner—Fenway’s cooler cousin. Start at Allium Market with a George Howell coffee and a loaded avocado toast. (Radishes! Runny eggs!) Spend a few hours browsing new fiction and coffee table books at Brookline Booksmith—I usually end up buying about three books from the bargain table. Since it’s the beginning of September and everyone you know just moved, head next door to Boston General Store, where you’re bound to find tons of locally made or globally sourced options for housewarming gifts. Grab a wood-fired pizza at Prairie Fire to hold you over until 7pm, which this year is the one-night-only showtime at Coolidge Corner Theater for the 1975 classic Jaws.

—Michele Snow, Art Director, Special Projects


ICA Watershed / Photo by Madeline Bilis

In part because it rules, and in part because it’s free on Labor Day, you’ll find me at the ICA’s flagship museum in the Seaport, which has some interesting and important exhibits right now. Then I’ll hop on one of the ICA’s free water taxis (big fan of being on the water for free) and head to the Watershed, its cavernous and very cool new satellite spot in Eastie. KO Pies is right next door and serves the best Australian food this side of the hemisphere, but sadly it’s closed on Mondays. So it’s back across the harbor for a burger and old fashioned at Drink. Cheers!

—Spencer Buell, Staff Writer


For a true staycation, I stay put in my favorite little ‘hood, JP. Iced coffee and bagels from Exodus is perfect fuel for a walk (or sail) around Jamaica Pond, followed by a stroll on Centre Street. Kitchenwich and On Centre are two of my favorite shops but I always save the best, Boomerangs, for last. I dare you to leave that store without a new treasure tucked under your arm. Take an afternoon bike ride to Allandale Farms to wander among the plants and get snacks for a pondside picnic. Close out with happy hour at Turtle Swamp Brewing, dinner at Tres Gatos, and a nightcap at Galway House, which is always decked out in seasonal decorations. Happy Labor Day!

—Abby Bielagus, Lifestyle Editor


Flavor overload at the Ice Creamsmith in Dorchester / Photo by Anthony Adamick (OV Stills)

Though I’m a year-round ice cream addict, Labor Day weekend marks one of the few remaining times of the year where you can use scorching temps as an excuse to devour ice cream like it’s a primary food group. I say, take advantage of that by spending your Monday off visiting all of your favorite local ice cream shops, from Fomu, to Gracie’s, to J.P. Licks, and more. (Perhaps you should consult our list of Boston’s 28 essential ice cream shops.) So, in other words, eat as much ice cream as humanly possible in one day.

—Rachel Kashdan, Staff Writer


places to propose arnold arboretum

Photo by Jon Hetman/Arnold Arboretum of Harvard University

Renting a bike and pedaling along the Esplanade, through Harvard Square, and along the Cambridge side of the Charles is one of my favorite ways to see the city. But on Labor Day, I figure I should switch things up and head the opposite direction to explore all 281 acres of the Arnold Arboretum. (Hello there, fog sculptures.) This literal urban oasis is home to 15,000 living plants, representing 4,000 kinds of trees, shrubs, and vines. It’s a really nice getaway from the hustle and bustle—which is really what we need on a day off, amiright? Afterward, I’m heading straight to Juicygreens for that magical-looking blue smoothie.

—Tessa Yannone, Wellness Editor