Holiday Weekend in Falmouth, Massachusetts

A crowd was gathering near the bandshell in Falmouth’s Marina Park, puffy parkas buttoned to the top against the brisk early-December breeze. Kids rolled down the hill toward the water as dogs donning antlers milled about—and all eyes scanned the horizon.

Suddenly, the Quickwater puttered into view and the merry mob cheered. There, at the bow of the Vineyard shuttle, was Seafaring Santa, alternately waving and making a heart with his gloved hands. The boat docked and Santa, with a hearty “Ho-ho-ho!” stepped ashore and began passing out candy canes to the little ones surging forward. Just in front of me, a man in an elf hat turned to his friends. “This town takes Christmas seriously,” he said.

He’s right. Thanks in large part to the long-standing annual Falmouth Chamber of Commerce’s Holidays by the Sea weekend, the Upper Cape town offers festive opportunities both raucous (the bustling Falmouth Village Holiday Stroll, the Jingle Jog 5K, the Christmas Parade) and relaxing (moonlight caroling in Woods Hole, a walk in the Ashumet Holly Wildlife Sanctuary) come yuletide.

We’ll get to all that—but first, wine. My inaugural stop in town Friday afternoon was at East Falmouth’s Cape Cod Winery, where I braved temps in the mid-20s with steaming mulled wine at a picnic bench warmed by a tabletop firepit. From my perch near a hedge bedazzled with ornaments and glitter letters spelling “M-E-R-R-Y,” I counted no fewer than 16 wreaths. A handful of other patrons took their wine-based cocktails straight to the heated enclosed deck; the bartender told me the winery was expecting hordes for an upcoming ugly-sweater party.

I had my own evening festivities to get to, so I paid the tab and dropped my bags at The Coonamessett before continuing to the village of Woods Hole. While it seemed quiet at first, people quickly formed a long, winding line down Water Street at 5 p.m. sharp for the trolley strung with twinkling lights to Nobska Light.

As if an end-of-the-world bluff illuminated by the year’s final supermoon wasn’t a magical-enough setting, there was a brass ensemble playing “Silver Bells” in the base of the 40-foot-tall lighthouse as Mrs. Claus awaited visitors with hot chocolate and cookies in the keeper’s house. It felt special, a sneak peek into a historical place not everyone gets to see, and I couldn’t help beaming on the short ride back to the village.

The dulcet sounds of yet more carolers drew me to Waterfront Park after I hopped off the trolley. There, the Solstice Singers and a small crowd ringed a stacked lobster-trap tree, snapping photos, singing along in hushed tones, and sipping cocoa. The tree’s creator, Greg Dolan, a commercial fisherman, carefully scaled the sculpture to place a buoy “star” at the top. Back on solid ground, he proudly told me that construction took two days and 87 (!) traps.

I capped off the cold, clear night with dinner at Water Street Kitchen’s welcoming bar. It seemed that everyone in Woods Hole that evening had the same idea, and what a good idea it was: going from the lighthouse tour to caroling to cioppino and craft cocktails.

While my husband and 6-year-old daughter arrived too late the next morning to see Seafaring Santa make his grand harbor entrance, we caught up with him at the Marine Lodge downtown, where he spent most of the day receiving families and handing out candy canes, cookies, and, yes, more cocoa (truly, the Holidays by the Sea weekend runs on free hot chocolate).

Properly fortified and not a little high on sugar, we drove to the circa-1878 Highfield Hall & Gardens for its 19th annual Holidays at Highfield display. The theme changes each year, and for “The Shopkeepers’ Noël,” the historical estate’s rooms had become charming Victorian-era stores. My daughter was most enchanted by the story room, brimming with holiday books and child-sized wooden toadstools for reading them, and the crafts nook, where we made tussie-mussies from cardstock, pipe cleaners, and greenery, and tucked pine cones and tinsel into clear plastic ornaments.

The midday rain cleared, and when we returned downtown, several jolly inflatables bobbed at the edge of the Falmouth Public Library lawn: Frosty, Rudolph, a nutcracker, and Santa hat–wearing dinosaurs among them. My husband and daughter set off for Mullen-Hall School for a free ride on the Carousel of Light (a local institution hand-carved in the ’90s by artist Lance Shinkle), and I hit Main Street for the Holiday Stroll. Going on the early side had its advantages—it was easier to browse the well-curated bookstore Eight Cousins and cutest-ever kids’ boutique Caline for Kids, and there were zero lines for the adult beverages and treats on offer—but rowdier fun arrived with the masses.

The party continued as I reunited with my family and we joined the throngs moving toward the Falmouth village green. Kids clutched flashlights and glow sticks as the countdown began … 10, 9, 8, 7, 6, 5, 4, 3, 2, 1 … and the lights switched on. The central tree, a menorah, Santa’s sleigh, shadow-box vignettes sprinkled around the green—all were illuminated. “It’s electric,” Falmouth Chamber of Commerce deputy director Maura Aldrich told me. “Everyone is just so joyful.”

So much joy that we all slept in the next morning. The promise of Maison Villatte finally got us out of bed—a croissant aux framboises and a pain au chocolat for a little sweet, and a quiche champignon for something savory. And for a quiet start to Sunday, we decamped to Ashumet Holly Wildlife Sanctuary, just a short drive from downtown. My daughter and I strolled hand in hand on winding paths through the almost 50-acre East Falmouth property, home to 65 varieties of the wintry flora. We peeped robins snacking on bright red berries and posed for a selfie with the “Tallest Holly” (45-feet-plus tall) on the Mystery Tree Trail.

Although we’d soon head back to civilization for the 62nd annual Falmouth Christmas Parade and its flotilla of decked-out floats, this was a moment for reflection, for fresh, bracing air, for simply enjoying each other’s company in a fleeting holiday season.

This year’s Holidays by the Sea weekend is 12/4–12/6. For more information, go to capecodchamber.org/falmouth-chamber.

Holiday Weekend in Falmouth, Massachusetts: The Guide

Things to Do in Falmouth, MA

Ashumet Holly Wildlife Sanctuary

In winter, the 1,000 holly trees at this Mass Audubon property are “in their full berrying glory,” says sanctuary director Ian Ives. See for yourself with a reinvigorating stroll on 1.5 miles of mostly flat trails.

Eight Cousins

After a few years of operating at two locations, indie bookstore Eight Cousins has consolidated its kid and adult offerings under one roof at 199 Main Street. In other news: The community mainstay—named after the children’s novel by Louisa May Alcott—just celebrated its 40th birthday.

Holidays at Highfield

While Highfield Hall & Gardens offers artist talks, live music, and classes throughout the year, the estate especially shines during Holidays at Highfield. Thursday through Sunday from late November to mid-December, catch whimsical decorations to match the annual theme, an artisan market, and more.

Masterson Made

Need gifts for your foodie friend, your Zoomer niece, or your crafty neighbor? Check (a chic cutting board), check (Atlantic Soap Co. lip shimmers), and check (a seascape paint-by-numbers kit). Stocking stylish items from near and far, this Woods Hole shop—helmed by husband-and-wife designers Patrick and Melissa Masterson—has your Christmas list covered.

Dining in Falmouth, MA

Maison Villatte

Choux à la crème, berry clafoutis, and croissants à la cannelle, mon Dieu! With two cheery locations—downtown and Woods Hole—this boulangerie keeps Falmouth blissfully stocked with oh-so-craveable French pastries.

Osteria La Civetta

Civetta means “little owl” in Italian, but don’t let this eatery’s cutesy name fool you—it’s got big pasta energy, serving up perfectly al dente tagliolini ai gamberi and butternut squash–filled tortelloni in a boisterous space on Main Street. All in all, it’s, um, a real hoot.

Pickle Jar Kitchen

Cucumbers are so pedestrian. The house-made fermented foodstuffs at this homey breakfast and lunch spot include pickled carrots, cauliflower, radishes, and more, and come alongside the stacked sandwiches. The Town Hall—with roast beef, Jarlsberg cheese, and red onions on toasted rye—is a standout.

Water Street Kitchen

Water views may beckon at this sea-to-table Woods Hole restaurant, but choose a seat at the convivial bar instead. Not only will you be closer to the expertly crafted cocktails, but you can also rub elbows with the regulars savoring shiso-scented swordfish belly in dashi and grilled oysters. Cozy indeed.

Lodging in Falmouth, MA

The Coonamessett

Done up in soothing neutrals, the guest rooms and common spaces at this classic-feeling Cape inn and events center are surely coastal grandma–approved. Close but not too close to downtown, The Coonamessett is also a short jog to the scenic Shining Sea Bikeway.

Woods Hole Inn

Stay where visiting scientists and researchers do: at this sleek 14-room bed-and-breakfast that’s allegedly 189 steps from the Martha’s Vineyard ferry. (We didn’t check their math, but it’s close by.) If you’re looking for more privacy or space, the inn also rents out three vacation homes, all walkable to the main drag’s restaurants and shops.

This feature was originally published in the November/December 2026 issue of Yankee.

Courtney Hollands

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