Massachusetts' Largest Ski Destination Is A Thrilling Winter Wonderland Bordering New York

There's no bad time to be in the Berkshires. Thanks to sunny weather, scenic trails, and a vibrant Massachusetts fine arts scene, historic towns like Williamstown are wonderful to visit in spring and summer. Samantha Brown chose the New England region as one of her top fall destinations. And in the coldest months, the Berkshires are a winter wonderland for skiers, snowboarders, and hikers, who head to mountain towns like Hancock to make the most of the season.

Located near the Massachusetts-New York border, Hancock is home to Jiminy Peak — the largest ski destination not just in Massachusetts but also in all of southern New England. With a summit of 2,380 feet, 167 skiable acres, and an average annual snowfall of 71 inches, it's a hotspot for winter sports enthusiasts throughout the season. The complex has 45 trails served by 12 lifts, as well as three terrain parks and snow tubing. Most ski trails at Jiminy Peak are beginner or intermediate (though, according to OnTheSnow, 27% are considered advanced, and another 7% feature expert terrain), which makes Jiminy Peak especially popular with families. It's no wonder the resort was honored several times as the "Best Ski Area for Beginners" by OnTheSnow's Visitors' Choice Awards. 

Another standout feature is that Jiminy Peak is the only ski center on the continent that uses alternative wind power to produce energy. It has a wind turbine that provides roughly a third of the resort's electrical needs throughout the year — and as much as half during winter, when the region's winds blow the strongest. Learn more about incredible eco-forward resorts exercising sustainable practices around the world.

Jiminy Peak typically opens in mid-November. By the time ski season is in full swing in December, all the lifts should be open, with operating hours from 8:30 a.m. to 10 p.m. On weekends and holidays, all-day lift tickets cost $124 for adults and $109 for kids, with slightly lower prices during the week. For those who don't mind colder after-dark temperatures, the resort offers night skiing on nearly two dozen illuminated trails. Twilight passes cost $69 for adults and children during peak times and $59 for all ages in non-peak times.

Apart from its ski resort, Hancock is a popular destination for winter activities both indoors and out. Bundle up for a hike or a snowshoeing adventure in the nearby Pittsfield State Forest, which has 30 miles of trails and is open daily from sunrise to sunset. Explore the scenic Shaker Trail, a tree-lined 5.4-mile loop near Hancock Shaker Village. One of Hancock's key attractions, this living history museum is dedicated to Shaker culture and is also the site of the oldest working farm in the region. Walk through the Hancock's permanent collections of Shaker furniture, art, textiles, and household objects; stop into the Woodlife Kitchen for a hot tea; or go for a snowy stroll on the village's one-mile Farm & Forest Trail.

This winter, in partnership with the Berkshire Museum, the village is hosting "Festival of Trees: Barn To Be Wild!" Open on weekends through December 28, the exhibition features trees that local organizations have decorated for the holidays. Tickets are $20 (children under 12 enter for free). 

Stay near the slopes at Jiminy Peak Mountain Resort (rooms from $209 per night), a ski-in, ski-out lodge with a ski shop and an indoor hot tub. Dining options at the ski center include the casual food court JJ's Lodge, coffee and sandwich shop Café Veloce at Crane Lodge, and the cozy John Harvard's Restaurant & Brewery, with views of the mountain through large picture windows.

Alternatively, rent an Airbnb in Hancock with scenic views, and go for dinner at Bluebird & Co., a rustic-chic eatery set on the banks of a mountain brook. With indoor and outdoor seating, gourmet comfort food, and a full bar, it's a local favorite — and it's located within walking distance of the ski resort. 

Hancock is less than an hour's drive from Albany — New York's oldest town, a history-rich gem with world-class museums — and its international airport. Expect a 45-minute ride with the usual traffic. You'll want a car to navigate the area, as it's not well served by public transportation.