Season’s Best: Winter Activities in the Northeast

Some Northeast towns are at their most dazzling in the dark days of winter, when they embrace the frosty clime and play host to annual festivals. We offer a guide to three one-of-a-kind celebrations in locales that are worth exploring at any time of year, but best of all when the winter wind blows. Button up your overcoat and head to Westchester, Connecticut, and beyond.

Holly Days, Westport, CT (Through Dec. 31)

Westport is always lively, even in the dead of winter. “Our downtown is very walkable and contained,” says Ramin Ganeshram, executive director of the Westport Historical Society. “There are cultural events and a really good restaurant scene, which draws people downtown.”The town center is situated along the Saugatuck River, which flows out to Long Island Sound. “It’s an outdoorsy town,” Ganeshram says, adding that residents walk on Compo Beach all year long as well as ice-skate on the popular outdoor rink in Longshore Park in the cold months. Westport has attracted artists since the late 19th century, and current cultural offerings include shows at the Westport Country Playhouse, which former locals Paul Newman and Joanne Woodward helped rebuild and actively supported.

Each December, there are holiday house tours, horse-and-carriage rides, and a popular First Night celebration on NewYear’s Eve. This year, the Historical Society launched
a broader monthlong Holly Days festival, which includes wreath-, candle-, and ornament-making workshops; boxwood and heritage-tree decorating; a winter solstice storytelling event; and a gingerbread house–making contest during which participants are encouraged to re-create some of the village’s best-known buildings, such as the Italianate/ Victorian home of the Historical Society, the seven-sided Bradley Wheeler Cobblestone Barn, and the two recognizable bridges that straddle the Saugatuck River.

Harvard Square Chocolate Festival, Cambridge, MA (Jan. 25-27)

Chocolate in all forms is the attraction at the Harvard Square Chocolate Festival, now in its 11th delicious year. All weekend long, restaurants in and around this Cambridge enclave offer specialty chocolate desserts and cocktails—and even incorporate essence of chocolate into pork, chicken, and beef entrées. The highlight of the weekend is on Saturday afternoon, when about 15 restaurants put out free chocolate samples for the 2,000 festival-goers, including students, residents, and tourists. “It’s usually very cold, and sometimes it’s snowing, but there’s free hot chocolate and a band playing, and it gives people a reason to be outside in the cold weather,” says Denise Jillson, executive director of the Harvard Square Business Association. History is palpable in the Boston suburb best known as the home of Harvard University, founded in 1636. “We also have Cambridge Common, where General George Washington commandeered troops to fight the British,” says Jillson, noting that Cambridge is actually an eclectic collection of neighborhoods. “MIT is at Kendell Square about a mile away from here, and it’s a completely different environment. In between is Central Square, and then there’s Inman Square, which is more village-like. They’re all little spaces with their own identity, but they come together in this lovely cohesion that we like to think of as the hub of the universe,” says Jillson.

Westchester’s Winter Wonderland, Valhalla, NY (Through Dec. 31)

In the shadow of architecturally stunning Kensico Dam, Westchester’s Winter Wonderland has drawn more than 100,000 merrymakers since its 2014 inception, according to Elyssa Martinez, program and recruitment coordinator for the Westchester Parks Foundation. “Most of our guests come from a 30-mile radius around the dam,” Martinez says. The wintry event is a major production: Organizers bring in an outdoor ice rink (complete with skate rentals), rides, a circus, and a light show set to holiday music. Santa Claus makes nightly appearances, as does an eclectic convoy of food trucks.

Kicking off with a tree-lighting ceremony the night after Thanksgiving, the festival lights up nights through NewYear’s Eve, which is celebrated with a pyrotechnic show and a family-friendly ball drop at 8 p.m.

The 307-foot-tall granite and concrete Kensico Dam, completed in 1917, and the surrounding public park, Kensico Dam Plaza, offer scenic vistas all year round. The site of The Rising—a soaring memorial to the 109 Westchester residents who died on 9/11—the park is the centerpiece of Valhalla, a small, quaint community in the heart of Westchester County. Home to Westchester County Medical Center—which sponsors the holiday festival—and Westchester Community College, Valhalla has a small, walkable downtown with restaurant options that include Chinese, Indian, and Italian cuisine, as well as Valhalla Crossing, which serves “American comfort fare” in a 1910 train caboose and an 1896 railway car.

—By Bernadette Starzee

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