Winter Fun In Pittsfield

Winter is a magical time in the Berkshires, and Pittsfield is at the center of it all. Ski on our action-packed downhill slopes or explore pristine trails on your cross-country skis, snowshoes, or hiking boots at several scenic parks and the gorgeous Pittsfield State Forest. With three hours to spend, you can create loads of outdoor family adventures.

Don’t miss the 10×10 arts festival held every February for 10 days. It’s a celebration of winter and the arts with family-friendly indoor and outdoor activities at locations throughout the city. Pittsfield is definitely the happening place to be all winter long!

Start Your Outdoor Adventure

Before heading out on your winter adventure, fuel up with a hearty breakfast or lunch at one of our tasty cafes where you’ll find satisfying delights like homemade omelets, blueberry pancakes with locally-sourced maple syrup, homemade pastries, artisan burgers, pizza, salads, and more.

Or re-charge at one of Pittsfield’s many coffee shops with comforting drinks like golden turmeric milk, chai lattes, and fresh locally-roasted coffees.

Make Sure You Are Equipped

Exciting outdoor fun is all about making sure that you are warm and have the right clothing and gear. As the Norwegians like to say, “There is no such thing as bad weather, only bad clothing.” 

The family-owned Plaines Bike Ski Snowboard has you covered from head to toe. They have an extensive collection of winter clothing, including base layers, gloves, and boots. You can get high-quality skis, snowboards, bindings, boots, and helmets to buy or rent.

Kids and adults also love The Garden, in the heart of downtown, for all their snowboarding needs. Their selection of boards, boots, and bindings for purchase or rent will enable you to tackle the snow in style. With its trendy outdoor clothing lines, accessories, and expert staff, you’ll not only have some of the best gear around, but you’ll look amazing too.

Berkshire Bike and Board offers snowshoes as well as gloves, helmets, and goggles. For the adventurous biker, they have winter clothing to keep you warm on your wheels.

Hit the Slopes

The much anticipated, newly renovated 200-acre Bousquet Mountain is on everyone’s list this winter for skiing, snowboarding, and tubing. Located in South Pittsfield on the northern summit of Yokun Ridge within the Taconic Mountain Range, it’s just minutes from downtown. It boasts 23 trails, a 750-foot vertical drop, and 85% snow coverage.

A family-friendly ski resort dating back to 1932, Bousquet is a beloved Pittsfield treasure. It’s not unusual to meet skiers here who have been coming for over half a century, who brought their children and now their grandchildren to ski its time-honored slopes.

There are many pricing options from 4-8 hrs, discounted night skiing (after 4 pm) and season passes. Group and Private lessons are available for skiers & snowboarders ages 2 and up, and adult and kid racing clubs are popular with locals.

If tubing is your preference, Bousquet offers up to 8 tubing lanes, and a Carpet Lift that makes getting back to the top of the tubing hill easy. One-hundred percent snow-making coverage ensures there is snow, even when you may not have it in your backyard!

After several rounds of runs, you’ll want to warm up in the newly built, open-aired, modern lodge with amazing views of the mountain. Locals will especially appreciate the mural wall of photos as they recognize familiar faces from years past.

Enjoy a drink or a meal as you take in panoramic views of the mountain at the Lift Bistropub, located on the second floor of the lodge. A full-service bar and restaurant, Lift features everything from quick snacks to dinners and desserts. Soups, salads, and flatbreads round out the menu along with an assortment of cocktails, wines and local beers.

Back Country Snow

Hike up your long johns. grab the cross-country skis, snowmobile, or snowshoes after a snowfall and head out.

The 11,000-acre Pittsfield State Forest is the ideal place for backcountry skiing, snowmobiling, or snowshoeing. It offers 30 miles of trails that wind through the mature woods. Many trails are specifically groomed for snowmobiles by the non-profit Berkshire SnowSeekers Snowmobile Club. Others are too narrow and reserved for non-motorized travel. (If you take your snowmobile, be sure you have a valid Massachusetts snowmobile registration. It is required to ride on public lands in the state.)

Canoe Meadows or Springside Park offers a one-of-a-kind x-country skiing or hiking experience. Even in the winter at Canoe Meadows you may spot ducks, birds, and other woodland creatures. You can’t miss the large beaver dams in the middle of the waterways and it’s the perfect spot to explore animal tracks. As the largest municipal park in Pittsfield, Springside covers 237 acres on the north side of the city and has miles of trails perfect for snowshoeing, cross-country skiing, or hiking any time of year.

Sledding

If you’re looking for a zero-cost family bonding experience, explore sledding on Pittsfield’s many hills at locations throughout the city, including Clapp Park, Osceola Park, Kirvin Park, and Reid Middle School.

There’s nothing like a good old-fashioned morning or afternoon of sledding with the kids to take you back to those halcyon days of youth where the joys of a snow day were only matched by the exuberant cheers of zooming down freshly fallen snow.

Skating

Practice your Hamill Camel or hockey maneuvers downtown at the Boys and Girls Club of the Berkshires Skating Rink. Open skates are every Saturday & Sunday from 3:30 pm – 4:30 pm and the cost is between $5-7. Skates can be rented for $5 per session (while supplies last). Hours may be affected by Covid-19 protocols so be sure to check the website or call before heading out.

Ice Fishing

Ice fishing enthusiasts from all over New England come to Pittsfield’s signature lakes, Pontoosuc and Onota, to catch the big one. Once the lakes freeze in the Berkshires, you’ll see folks camped out for a day of ice fishing on both of these gorgeous lakes. Be sure to stop at Onota Boat Livery for ice fishing supplies including equipment, tackle, and bait.

Hiking + Wildlife Tracking + Forest Bathing

Spending time in the woods in the winter is medicine for the soul – the quiet simplicity of the forest is instantly gratifying as it strips away our worries and tension. Studies show that as little as 40 minutes of walking in the forest can bring about elevated mood and lower cortisol levels!

A popular Pittsfield pastime is pursuing animal tracks and endeavoring to guess what type of animal created them. Take your time strolling through the woods to see what delights you might find. Or try a nighttime jaunt – looking (and listening) for owls during prime mating season is a great excuse to be in the woods. (Be sure to bring your ice cleats/spikes and trekking poles as there can be icy spots.

Check out the programs at Berkshire Natural Resources Council (BRNC) and Mass Audubon/Canoe Meadows for guided hikes and talks that are entertaining and educational for the whole family as well as our online event calendar.

Indoor Fun

When you’re ready for a break from outdoor adventures, spend an afternoon at the newly renovated Berkshire Museum where children can explore their curiosity walking through their permanent and changing exhibits as well as experience the many hands-on events the museum offers.

Maybe you’d prefer to luxuriate in heated reclining seats as you catch a feature film at the downtown Beacon Cinema, where the stadium seating guarantees a great seat for everyone. (A full concession stand as well as beer and wine are available.)

For the adults, there’s no better way to beat the winter blues than with live music and a hot toddy or cocktail at various venues throughout the city.

The cultural highlight of the winter in Pittsfield is the annual 10×10 Arts Festival, now in its 11th year. A collaboration between more than a dozen arts and cultural organizations, it brings more than 10,000 people downtown for ten days in the middle of February to enjoy indoor and outdoor activities for every age. Experience hand-crafted ice sculptures, theater, educational events, fireworks, and more! Meant to coincide with school vacation, the full lineup of events will keep the kids and adults busy all week long. Be sure to get your tickets early for the popular 10×10 Play festival performed by actors at the award-winning Barrington Stage Company. Ten original plays, each ten minutes long, filled with funny and poignant moments make this a beloved 10×10 tradition.