There's something about a mountain town in the winter. Cozy restaurants, Adirondack chairs around a fire pit at a lodge, family-friendly ski mountains, a classic diner, and decorated Main Streets. Vermont, New York, Maine, and New Hampshire offer some of these quintessential and oh-so-nostalgic mountain towns. They do, however, come with a longer travel time and higher cost.
A solution for the coastal Connecticuters who want a more budget-friendly option that is also a little closer to home? The Berkshires. The Berkshires are a section of Western Massachusetts where the Vermont-based Green Mountains spill into the Bay State.
The largest municipalities associated with the Berkshires cultural region include Pittsfield, North Adams, Great Barrington, Williamstown, Stockbridge, Lee, and Lenox. The highlands of Massachusetts don't boast towering jagged peaks but instead, host smaller peaks ranging from about 700 to 1,200 feet. The area is home to a few different ski resorts, Butternut, Berkshire East and Jiminy Peak being the most well-known. The mountain towns on a small scale which generally means easy access, less crowded, and more affordable options.
Couples trip, girls weekend, solo exploring, a long day trip, or a weekend away with the family. If you want to explore mountain towns in the winter, the Berkshires are a great option.
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| Norman Rockwell Museum |
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| Downtown Stockbridge, MA |
Towns to visit
Lee - Visit the outlets, stop by High Lawn Farm (working dairy farm), walk the classic downtown Main Street
Lenox - Visit the Ventfort Hall Mansion and Gilded Age Museum or The Mount (estate of Edith Wharton)
Stockbridge - Walk the quaint Main Street, hike to Laura's Tower, visit the Norman Rockwell museum
Pittsfield - Hike Pittsfield State Forest, visit the Berkshire Museum, Hancock Shaker Village
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| Winter Lights, Berkshires |
Holiday Events
Winter lights at Naumkeag
"Winter Festival: Solstice Celebration" at the Berkshire Museum
Nightwood at The Mount
Stockbridge Main Street at Christmas
Hancock Shaker Village Holiday Nights
Romantic Relaxing
The Berkshires are dotted with quaint inns and resorts that offer the ultimate one-stop shop for R&R. Check out this list of spas in the area which includes favorites like Canyon Ranch (Lenox), Cranwell Spa & Golf Resort (Lenox), and the Lotus Salon and Spa (Pittsfield).
With Kids
We brought our son to the Berkshires with us and we were happy to see so many family-friendly options. Winter Lights is the perfect event to bring the kiddos. The Norman Rockwell Museum has a large property with trails where kids can get the wiggles out before enjoying some quiet time in the museum. Check out some of the playgrounds in the area - the playground at Stockbridge was the perfect start to a chilly Saturday morning in Stockbridge.
Ski
Butternut: 5 lifts, 22 km of trailsBerkshire East: 4 lifts, 13 km of trails
Jiminy Peak: 7 lifts, 9 km of trails
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| Laura's Tower and the Ice Glen Trail |
Hike
Hiking is a little limited in the winter months - unless you have the right gear! Snowshoes and microspikes allow you to get out into the trails even when they are snow-covered or icy.
The Appalachian Trail - the famous AT traverses through the Berkshires. Hike a segment!
Laura's Tower and the Ice Glen Trail (Stockbridge)- this gorgeous trail departs right from downtown Stockbridge. We did this in the fall but a great option in the winter with the right gear.
Mount Greylock - Massachusetts's tallest peak sits in the Berkshires. We hiked this in the summer and again in the colder months and it was pretty dreamy every time.
Stevens Glen (West Stockbridge) - A 1-mile loop trail that is great for all ages.
Bash Bish Falls (Mt Washington)- 2 mile hike and a great scenic option to see the frozen waterfall in the winter months.
October Mountain (Lee) - Great snowshoeing option in the winter - 7 mile loop for advanced hikers
Eat
Joe's Diner (Lee) - Classic Berkshires old-school diner
Red Lion Inn (Stockbridge) - historic inn serving up great classic dishes
BB's Hot Spot (Pittsfield) - Caribbean food
Gateways Inn (Lenox) - beautiful dining room, great menu
Main Street Cafe (Stockbridge) - fantastic lunch option
Brava (Lenox) - great for late night
Alta Restaurant and Wine Bar (Lenox)
Timothy's Restaurant (Lee) - great Italian and pizza
Weekend Itinerary
Friday: Head up to the Berkshires after lunch. Plan an early dinner in the area before heading to Winter Lights (grab tickets early!)
Saturday: Start off a slow morning with coffee at one of the local coffee shops and a trip to the playground. Peruse one of the Main Streets and warm up during lunch. Head out after lunch to the Norman Rockwell museum. Enjoy dinner and drinks before heading back to your hotel or inn.
Sunday: Pack up for your return trip home and leave out a hiking bag or your ski gear. Check out some of the local trails, our favorite being the Ice Glen Trail in Stockbridge. If you prefer to spend the day on skis, check out our favorite Berkshire mountain, Ski Butternut. Rather relax? Check out one of the local spas.
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