Windsor MassachusettsATTRACTIONS & THINGS TO DO


Listed below are the best attractions and things to do near Windsor, Massachusetts.



1. Notchview

NORDIC SKIING AND HIKING


Notchview is a renowned Nordic skiing destination, attracting visitors year-round for cross-country skiing, hiking, and birdwatching. Spanning over 3,000 acres, it offers well-maintained trails through picturesque Berkshire landscapes. Outdoor enthusiasts flock to Notchview for its reliable snow, varied terrain, and peaceful natural beauty.


2. Windsor State Forest

DEEP WOODS & WATERFALLS


Windsor State Forest provides a tranquil retreat with deep woods trails, the scenic Westfield River, and sunny picnic fields. One of the highlights is Windsor Jambs, where a brook plunges between towering granite walls for a stunning waterfall display. Visitors enjoy hiking, mountain biking, fishing, and wildlife watching in this peaceful setting.


3. Wahconah Falls State Park

PICTURESQUE WATERFALL PARK


Wahconah Falls State Park is celebrated for its beautiful cascading waterfall surrounded by lush woods and tranquil picnic spots. It's a favorite destination for photographers, hikers, and families looking for a quiet day in nature. The waterfall, especially after rain, is a dramatic and memorable sight in the Berkshire landscape.


4. Eugene Moran Wildlife Management Area

WILDLIFE AND BIRDWATCHING


The Eugene Moran Wildlife Management Area provides a sanctuary for diverse bird and animal species across forests, streams, and wetlands. Outdoor lovers visit for birdwatching, hiking, and hunting in a serene, natural environment. The area's varied habitats make it especially appealing to wildlife photographers and nature enthusiasts.


5. Bas Ridge Golf Course

SCENIC PUBLIC GOLFING


Bas Ridge Golf Course, located nearby in Hinsdale, offers a scenic, well-maintained 18-hole course set against beautiful rolling hills. Golfers of all skill levels appreciate the relaxed atmosphere and welcoming staff. It's a popular outing for both locals and visitors seeking outdoor recreation in the Berkshires.



6. Berkshire General Store

LOCAL GOODS AND GIFTS


Berkshire General Store offers a wide range of locally made foods, crafts, and gifts with a Berkshire twist. Shoppers find jams, maple syrup, artisanal chocolates, and souvenirs that provide a taste of the region. It's a popular stop for those seeking unique mementos or edible treats from Western Massachusetts.


7. Windsor Jambs

GEOLOGICAL GORGE AND FALLS


Windsor Jambs is a striking geological gorge, where a brook cascades between 80-foot granite walls creating a dramatic chasm and waterfall. Adventurers and photographers are drawn to its rugged beauty and peaceful surroundings. The short hike to the falls is a favorite for families and nature lovers.


8. Guido's Fresh Marketplace

SPECIALTY FOODS & MARKET


Guido's Fresh Marketplace is known for its high-quality produce, artisanal cheese, and gourmet foods sourced both locally and internationally. Visitors enjoy browsing its vibrant aisles filled with organic groceries, baked goods, and specialty items. The market is a culinary destination for foodies exploring the Berkshires.


9. Hilltop Orchards & Furnace Brook Winery

ORCHARD TOURS & TASTINGS


Hilltop Orchards combines pick-your-own apple orchards with Furnace Brook Winery, offering tastings of locally produced wines and hard ciders. Visitors can enjoy scenic views, farm-fresh products, and miles of walking trails. Seasonal events and a welcoming farm store make it a favorite for families and couples alike.


10. Marketplace Cafe

CAFE DINING DOWNTOWN


Marketplace Cafe, located in downtown Pittsfield, is a popular eatery featuring sandwiches, salads, baked goods, and coffee made from high-quality local ingredients. The friendly, inviting atmosphere makes it a favorite for locals and visitors looking for a casual meal or coffee break. Art displays and live music add to its community vibe.



11. Otis Ridge Ski Area

FAMILY-FRIENDLY SKIING


Otis Ridge Ski Area is a classic, family-friendly ski hill offering affordable day and night skiing and snowboarding. Known for its welcoming vibe and gentle slopes, it's ideal for beginners and families introducing kids to winter sports. Ski and snowboard rentals are available on-site, making it easy for everyone to hit the slopes.


12. The Bookloft

INDEPENDENT BOOKSTORE


The Bookloft is an independent bookstore well-loved for its knowledgeable staff and wide selection of new releases, classics, and local authors. Bookworms enjoy browsing its inviting shelves and attending author events or readings. Its cozy atmosphere and carefully curated stock make it a must-visit for literary enthusiasts.


13. Bizen Gourmet Japanese Restaurant & Sushi Bar

JAPANESE CUISINE AND SUSHI


Bizen Gourmet Japanese Restaurant offers an extensive menu of expertly prepared sushi and Japanese dishes in an artful setting. Known for its fresh seafood and unique specials, it draws both locals and visitors seeking authentic Japanese flavors. The tranquil ambiance and attentive service make for a memorable dining experience.


14. Berkshire Museum

REGIONAL ART AND SCIENCE


The Berkshire Museum is a family-friendly attraction featuring engaging exhibits that span art, science, and history. Visitors explore everything from natural science dioramas and aquariums to hands-on children's areas and regional art collections. Its central location in Pittsfield makes it an accessible and popular stop for all ages.


15. Olde Forge Restaurant

FAMOUS WINGS AND PUB


Olde Forge Restaurant is famous for its award-winning chicken wings and extensive craft beer selection, served in a cozy, rustic pub setting. With hearty New England fare and a lively, welcoming atmosphere, it's a favorite with both families and groups. The Olde Forge's classic comfort food and laid-back style are beloved by locals and visitors alike.