Top Berkshire Activities for Seasonal Stays

The Berkshires – A Year-Round Destination

Tucked into the rolling hills of western Massachusetts, the Berkshires are a place where each season brings its own kind of magic. Spring blooms with fresh greenery and maple festivals, summer hums with lakeside energy and outdoor concerts, fall transforms the hillsides into a portrait of color, and winter blankets the region in a sparkling wonderland perfect for skiing and cozy evenings by the fire.

With its lakeside cabins, open grounds, and central location, Prospect Berkshire makes the perfect basecamp. You can spend the morning exploring nearby trails or cultural landmarks, and be back in time to unwind by the water or relax in your garden-inspired suite.

Spring Activities in the Berkshires

Spring is one of the best times to enjoy fresh air and blooming landscapes in the Berkshires. The season brings a sense of renewal, making it perfect for travelers who want to reconnect with nature and slow down after the winter months.

Maple Sugaring Tours – March is maple season in Massachusetts, and local sugar houses like Ioka Valley Farm invite visitors to see how sap is collected and boiled into pure maple syrup. Many farms even offer tastings and homemade treats – a sweet way to start your day.
Scenic Nature Walks – Trails at Housatonic Flats and Pleasant Valley Wildlife Sanctuary come alive with spring wildflowers and migrating birds. It’s a wonderful way to ease into the outdoors with a gentle, family-friendly walk.
Garden Tours – Explore the lush landscapes at Naumkeag or the historic grounds of The Mount as tulips, daffodils, and flowering trees brighten the scenery. These spots offer picture-perfect moments for couples and families alike.
Spring Festivals – Celebrate the season at local events like maple festivals, community art fairs, and early farmers markets, where you can shop handmade goods and taste the flavors of spring.

Summer Activities in the Berkshires

Summer is when the Berkshires truly shine. Long sunny days mean more time to explore, while warm evenings invite you to linger outdoors under the stars. Whether you’re drawn to water adventures or cultural events, there’s no shortage of Berkshire activities to enjoy.

Kayaking & Paddleboarding – Launch a kayak or paddleboard right from Prospect’s private lakefront access, or head to Canoe Meadows for rentals. Calm waters make it a relaxing outing for beginners and families.
Swimming at Local Lakes – Take a dip in Onota Lake or Laurel Lake, both just a short drive away. These scenic swimming spots are ideal for cooling off and enjoying a day in the sun with friends or pets.
Farmers Markets – The Great Barrington Farmers’ Market and Pittsfield Farmers Market are summer staples, filled with local produce, baked goods, and artisan crafts. It’s a chance to meet local growers and bring a taste of the Berkshires back to your cabin.
Tanglewood Concerts – Nothing says summer in the Berkshires like an evening on the lawn at Tanglewood. Spread out a picnic, sip local wine, and enjoy live performances from world-class musicians as the sun sets over the hills.

Fall Activities in the Berkshires

Autumn in the Berkshires is an experience that draws travelers from across New England. The crisp air, golden sunsets, and fiery foliage transform everyday walks and drives into unforgettable adventures. If you’re searching for fall activities in the Berkshires, you’ll find the region brimming with seasonal charm.

Scenic Foliage Drives – Take in breathtaking panoramas along the Mohawk Trail or wind your way through quiet backroads in the Berkshire Hills. Every curve reveals another view of brilliant reds, oranges, and golds.
Hiking Under the Canopy – Trails at Mount Greylock State Reservation and Bash Bish Falls State Park are at their most spectacular in the fall. Bring your camera, pack a thermos of cider, and enjoy crisp, leaf-covered paths that lead to sweeping views.
Harvest Festivals – Local orchards celebrate the season with apple picking, hayrides, and cider donuts. Town greens host craft fairs and farmers markets filled with pumpkins, mums, and local specialties.
Pumpkin Patches & Corn Mazes – For a family-friendly afternoon, head to Whitney’s Farm Market in Cheshire, where kids can pick their perfect pumpkin, navigate a corn maze, and enjoy fall activities designed with families in mind.

Winter Activities in the Berkshires

When snow blankets the region, the Berkshires become a winter wonderland. Whether you’re an avid skier or simply love cozy evenings by the fire, this season is full of memorable experiences.

Skiing & Snowboarding – The Berkshires are home to some of the best Berkshires winter activities. Mountains like Jiminy Peak and Bousquet Mountain offer everything from beginner slopes to challenging runs, plus lessons for all ages.
Snowshoeing & Winter Hikes – Explore serene snow-covered forests at Notchview Reservation or Canterbury Farm, where trails are groomed for snowshoeing and cross-country skiing. It’s a peaceful way to enjoy the quiet beauty of winter.
Sledding & Skating – Families love finding local hills for sledding or heading to outdoor rinks like the one at Paterson Field House for a fun afternoon on the ice.
Cozy Fireside Evenings – After a day of snowy adventures, return to your spacious cabin at Prospect Berkshire. Curl up with a blanket, sip hot cocoa or mulled cider, and watch snowflakes fall across the lake – the perfect end to a winter’s day.

Family-Friendly Fun All Year

The Berkshires are as much about culture and creativity as they are about the outdoors, making them a destination the whole family can enjoy no matter the season.

MASS MoCA (North Adams) – One of the largest centers for contemporary art in the country, MASS MoCA is both kid-friendly and endlessly inspiring.
Norman Rockwell Museum (Stockbridge) – A must-see for art and history lovers, showcasing the iconic illustrator’s works.
Berkshire Museum (Pittsfield) – A family favorite with hands-on science exhibits, aquarium tanks, and a planetarium.
Seasonal Events – From summer outdoor concerts to winter holiday lights and markets, there’s always something happening if you’re looking for activities in the Berkshires this weekend.

Why Stay at Prospect Berkshire?

Amid all these incredible Berkshire activities, you’ll want a place to return that feels like a retreat in itself. That’s where Prospect Berkshire comes in.

Here’s why guests love staying with us year-round:

Lakeside Gatherings

Stroll down to the resort’s private lakefront, enjoy the peaceful water views, or take a kayak or paddleboard out for a relaxed morning adventure. Dogs will love cooling off by the shoreline just as much as you.

Modern, Spacious Cabins

Stay in thoughtfully refreshed cabins with cozy interiors, plenty of space for families and pets, and direct access to the outdoors for easy morning walks.

Outdoor Wellness Features – The resort’s seasonal saltwater pool invites leisurely dips under the sun, while the Finnish-style saunas – both lakeside and in the pool house – offer rejuvenating warmth with stunning views and thoughtful amenities like tea, showers, and lockers.

Tennis & Pickleball Courts – For active guests, the well-maintained tennis and pickleball courts provide a playful, energetic alternative to lakeside lounging.

Close to Everything

Located in the heart of the Berkshires, Prospect is just a short drive from hiking trails, cultural landmarks, and popular Berkshires family activities, yet far enough from the bustle to feel like a private escape.

Culinary Excellence at The Cliff House

A restored 1876 timber structure at the heart of the property houses this divine restaurant. With both indoor and outdoor seating, local fare, community events, and lake views, it’s where guests come to connect

Pet-Welcoming Atmosphere

With no breed restrictions, complimentary treats, bowls, and waste bags, Prospect ensures your four-legged friends feel just as cared for as you do.

Plan Your Berkshire Escape

Whether you’re dreaming of wildflower hikes in spring, Berkshires winter activities, or a cozy family weekend full of fireside board games, the Berkshires are a destination for every season.

At Prospect Berkshire, comfort and connection come naturally. Taking a look at our offers, and start planning your trip with lakeside cabins, open-air spaces, and unbeatable access to the best of the region, it’s the perfect home base for exploring everything the Berkshires have to offer.

FAQs

What are the best family activities in the Berkshires?

Families love exploring the Berkshire Museum, hiking at Kennedy Park, and visiting local farms and seasonal festivals.

What can you do in the Berkshires in winter?

Top Berkshires MA winter activities include skiing at Jiminy Peak, snowshoeing at Notchview, sledding on scenic hills, and enjoying cozy evenings by the fire.

Where to stay for Berkshire activities?

For a central location near lakes, trails, and cultural attractions, Prospect Berkshire offers spacious cabins, lakeside access, and a welcoming, pet-friendly atmosphere.