Yankee Magazine FEATURE: Holiday Weekend in Cambridge, Massachusetts

A user’s guide to cornering the Christmas spirit in and around Harvard Square.

Originally published in the November/December 2025 issue of Yankee Magazine
By Courtney Hollands. Updated October 23, 2025.

Cambridge is a city of squares, each one vibrant, personality-packed, and deserving of exploration. But if you’re looking to ring in the holidays, head directly to the Harvard Square area, the epicenter of seasonal merriment as late fall slips into winter.

These festive vibes are due, in part, to how the namesake university’s brick buildings take on an idyllic European feel when snowflakes swirl. “Everything looks perfect,” said Ned Hinkle, creative director of The Brattle Theatre, just a few blocks down from the campus. “It’s how I imagine the experience of Christmas in London might be.”

And Harvard Square’s pealing church bells did inspire the writer and longtime Brattle Street denizen Henry Wadsworth Longfellow to pen his 1864 poem “Christmas Bells”: “I heard the bells on Christmas Day / Their old, familiar carols play / And wild and sweet / The words repeat / Of peace on earth, good-will to men!”

But spending a weekend here in mid-December makes clear that the neighborhood’s holly-jolly reputation comes down to its enduring holiday traditions: Midwinter Revels at Sanders Theatre, The Brattle Theatre’s screenings of It’s a Wonderful Life, the Harvard Square Holiday Fair market. These long-standing annual events hold special meaning for generations of families and friends and engender deep community.

That was the same community we encountered on a Saturday at Formaggio Kitchen in nearby Huron Village. No, really: It seemed like half of Cambridge’s 118,000-strong population had descended on the specialty-food store for spruce-wrapped Harbison cheese from Jasper Hill Farm, tinned fish, Belgian beer, and panettone galore.

Taken together, Huron Village and Observatory Hill, a pleasant stroll from Cambridge Common, are among the best shopping enclaves in the city—and we took our time browsing Cambridge Mercantile for hygge-perfect candles and “Ski You Later”–emblazoned sweaters and admiring GrayMist’s funky ornament array (hello, felted Ruth Bader Ginsburg).

Our last stop there was Imagine, a bustling, croissant-focused café from the team behind the venerable Cambridge bakeshop Iggy’s. Patrons jostled for a seat on sheepskin-lined benches near the crackling kiva-style fireplace; my husband and I stood as we sipped our turmeric chai latte and “Higher Being”—a far-out take on a spicy hot chocolate with Loco Love adaptogenic cacao blend, macadamia milk, and cayenne.

Sated, we arrived at Harvard University’s Sanders Theatre for the afternoon Midwinter Revels show, “The Selkie Girl and the Seal Woman.” Shoulder-to-shoulder with regulars who tittered at long-serving emcee David Coffin’s inside jokes, we took in the Celtic and Cabo Verdean rhythms and sea chanteys. The story was somewhat meandering, but it didn’t matter: We fell under the Revels’ spell, especially during the group sing-alongs to “Deck the Hall,” “Silent Night,” and “Lord of the Dance.” “It’s joyful theater,” says Revels executive director Diane Kennedy. “It’s that moment of, we’re all in here, and we’re all singing the same thing.”

Even hardened journalists can’t resist a fa-la-la, and we emerged from the historic hall beaming; families, arms linked, literally skipped past us. Considering that there were a few more names to cross off my gift list, we ducked into the Harvard Square Holiday Fairs—billed as “Peace, Love & Holiday Shopping Since 1986”—temporarily occupying an empty storefront on Massachusetts Avenue, near the Harvard Square T stop.

“You see the same faces,” cofounder Leslie Gray told me. “It’s like meeting your old friends.” It’s also like reconnecting with a bygone nuttier, crunchier version of Harvard Square: Importers displayed riotous textiles and jewelry from Africa and India alongside chatty artisans offering pottery, soaps, and terrariums—all while Steve Winwood warbled about “The Low Spark of High-Heeled Boys” over the speakers. No Mariah “Queen of Christmas” Carey here, by design.

Dinner at Pammy’s capped off a day of shared experiences, especially since we were seated at the glowy dining room’s pièce de résistance, a long communal table. With the nearby fireplace and the oversized centerpieces—earthenware vases overflowing with winter greens, bittersweet, and unexpected pink peonies flanked by candles and giant pine cones—it felt as if we were at a dinner party thrown by a posh but slightly eccentric aunt. At one point, while tucking into my squid ink gnocchi with lobster and furikake, I caught the eye of a stranger-turned-dining-companion across the table—he nodded as if to say, How magical is this?

My husband and I weren’t ready for the magic to end, so we hit Zuzu’s Petals for something sweet. We practically had to, considering the name of this jewel box of a wine bar comes from a scene in It’s a Wonderful Life, in which Jimmy Stewart’s on-screen daughter implores him to fix a crushed flower. (It felt doubly important because we couldn’t fit a screening of the Frank Capra Christmas classic at The Brattle into our jam-packed weekend.) Diners around us who were observing a more European suppertime dipped bread into steamy fondue pots as we shared a crème brûlée.

On our way back to The Charles Hotel, we walked through the gates of a hushed Harvard Yard, gloved hands shoved into pockets while our breath, visible, hung in the air. Thankfully there wasn’t snow in the forecast, as we planned to wake up and participate in one last act of radical holiday community: running with thousands of costumed joggers in Somerville’s annual Bill Rodgers Jingle Bell Run & Walk. It wasn’t yet Christmas day, but bells would be ringing. Longfellow would surely approve.

This feature was originally published in the November/December 2025 issue of Yankee.

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