The 30 Best Berkshires hiking trails in Pittsfield, Massachusetts

Berkshire Mountain Lodge is a charming lodging institution located at 8 Dan Fox Drive in Pittsfield, Massachusetts. Situated in the beautiful Berkshires region, the lodge offers a perfect blend of cultural attractions, historical sites, and natural beauty. Guests can explore nearby attractions such as The Mount, the former estate of American author Edith Wharton, and Tanglewood, the summer home of the Boston Symphony Orchestra. Berkshire Mountain Lodge is a family-friendly vacation destination that offers a variety of amenities and activities for guests of all ages. The resort has received numerous awards, including the RCI Gold Crown Status, Tripadvisor's Travelers' Choice Award, and the Hotels.com Loved by Guests Award, all of which recognize the exceptional service and hospitality provided by the lodge.

Life House, Berkshires is a charming lodging located at 194 Pittsfield Road in Lenox, Massachusetts. Nestled in the picturesque Berkshires region, this institution offers a peaceful and serene retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a welcoming atmosphere for visitors to relax and unwind. With its convenient location and warm hospitality, Life House, Berkshires is the perfect destination for a memorable getaway in the heart of the Berkshires.

Shaker Trail - Trailhead is a picturesque park located in Pittsfield, Massachusetts, United States. This tranquil institution serves as the starting point for the Shaker Trail, a scenic hiking and biking trail that winds through the beautiful countryside. Visitors can enjoy the natural beauty of the area, explore the historic Shaker sites, and take in the fresh air and peaceful surroundings. Whether you're looking for a leisurely stroll or an adventurous bike ride, Shaker Trail - Trailhead is the perfect place to connect with nature and enjoy the great outdoors.

Welcome to Pittsfield State Forest, a breathtaking natural sanctuary nestled in the heart of the Berkshires in Pittsfield, Massachusetts. Spanning over 11,000 acres, our park offers a perfect escape for nature enthusiasts, adventure seekers, and families alike. Explore miles of scenic hiking and biking trails, marvel at the stunning vistas from Berry Mountain, or enjoy a peaceful picnic by one of our serene ponds. Pittsfield State Forest is a haven for wildlife, providing opportunities for birdwatching and nature photography. In the warmer months, enjoy camping under the starry sky, while winter transforms the park into a wonderland for cross-country skiing and snowshoeing. Whether you're seeking solitude or adventure, Pittsfield State Forest is your gateway to the great outdoors. Visit us today and immerse yourself in the natural beauty of the Berkshires.

Welcome to Berkshire Knapsackers, your ultimate destination for outdoor adventure and relaxation located at 11 Churchill Street, Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape for nature enthusiasts and families alike. Explore our lush trails, perfect for hiking and bird watching, or enjoy a leisurely picnic amidst the stunning natural beauty. Whether you're seeking a peaceful retreat or an active day out, Berkshire Knapsackers provides a picturesque setting to reconnect with nature. Visit us today and discover the tranquility and charm of our beloved park.

Welcome to Pittsfield State Forest, a breathtaking natural haven located at 123-221 Potter Mountain Road, Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape for nature enthusiasts and adventure seekers alike. Spanning over 11,000 acres, Pittsfield State Forest is home to lush woodlands, sparkling streams, and stunning vistas that promise to captivate visitors of all ages. Explore a myriad of recreational activities, including hiking, mountain biking, and horseback riding along our extensive trail network. During the warmer months, enjoy picnicking, camping, and fishing in the tranquil setting of Berry Pond, the highest natural body of water in the state. In the winter, embrace the snowy landscape with opportunities for cross-country skiing and snowmobiling.

Welcome to Berkshire Mobile Home Park, your serene getaway nestled in the heart of the picturesque Berkshires. Conveniently located at 413 Pittsfield Road in Lenox, Massachusetts, our park offers a peaceful retreat for those seeking a unique lodging experience. Whether you're visiting for a weekend escape or an extended stay, you'll find comfort and convenience in our well-maintained facilities. Berkshire Mobile Home Park is not just an RV park; it's a community. We offer spacious lots with full hookups, ensuring you have everything you need for a comfortable stay. Our park is surrounded by the natural beauty of the Berkshires, providing a perfect backdrop for outdoor enthusiasts and nature lovers. Explore nearby hiking trails, enjoy the vibrant local culture, or simply relax and take in the tranquil surroundings.

Welcome to the Berkshire Natural Resources Council, a premier tourist attraction nestled in the heart of the Berkshires at 309 Pittsfield Road, Lenox, Massachusetts. Our mission is to preserve and protect the natural beauty and ecological integrity of the Berkshire region, offering visitors a unique opportunity to connect with nature. Explore our extensive network of scenic trails, perfect for hiking, birdwatching, and immersing yourself in the tranquility of the great outdoors. Whether you're a local resident or a visitor seeking adventure, our diverse landscapes of forests, meadows, and wetlands promise breathtaking views and unforgettable experiences.

Welcome to the Ashuwillticook Rail Trail Parking Area, conveniently located at 850 Crane Avenue in Pittsfield, Massachusetts. This well-maintained parking facility provides easy access to the picturesque Ashuwillticook Rail Trail, a popular destination for outdoor enthusiasts. Whether you're planning a leisurely walk, a scenic bike ride, or a peaceful jog, our parking area offers a safe and accessible starting point for your adventure. Situated in a serene setting, it is the perfect spot to begin your exploration of the trail's beautiful landscapes. Ample parking spaces are available to accommodate both local visitors and those traveling from afar. Visit us today and enjoy the natural beauty of the Berkshires right from your doorstep.

Welcome to Camp Arrow Wood, your premier destination for outdoor adventure and relaxation in the heart of the Berkshires! Nestled at 195 Cloverdale Street, Pittsfield, Massachusetts, our camp offers a serene escape from the hustle and bustle of everyday life. Whether you're seeking a weekend getaway, a summer retreat, or a place to connect with nature, Camp Arrow Wood is the perfect spot. Our beautiful grounds boast a variety of amenities and activities for all ages. Explore our extensive hiking trails, enjoy a leisurely paddle on our scenic lake, or challenge yourself with our ropes course and climbing wall. For those looking to unwind, our tranquil setting provides the ideal backdrop for meditation, yoga, or simply soaking in the natural beauty.

Welcome to the Barkerville Conservation Area, a serene and picturesque park located at 320 Barker Road, Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, this hidden gem offers a perfect escape for nature enthusiasts and tourists alike. Explore the lush landscapes and immerse yourself in the tranquility of the great outdoors, as you wander through well-maintained trails that wind through diverse ecosystems. At Barkerville Conservation Area, visitors can enjoy a variety of outdoor activities, including hiking, birdwatching, and picnicking amidst the stunning natural beauty. The park is home to a rich array of wildlife and offers ample opportunities for photography and quiet reflection. Whether you're seeking a peaceful retreat or an adventurous day out, Barkerville provides an ideal setting for all ages.

Welcome to Wild Acres - Observation Tower, a hidden gem nestled in the heart of Pittsfield, Massachusetts. Located on South Mountain Road, our park offers a serene escape into nature, perfect for families, adventurers, and nature enthusiasts alike. At Wild Acres, you'll find an array of natural beauty and outdoor activities to enjoy. The centerpiece of our park is the stunning Observation Tower, providing breathtaking panoramic views of the surrounding Berkshire landscape. Whether you're here to hike our scenic trails, enjoy a peaceful picnic, or simply take in the sights from the tower, Wild Acres offers an unforgettable experience for visitors of all ages.

Welcome to Balance Rock State Park, a serene natural oasis located on Balance Rock Road in Pittsfield, Massachusetts. Nestled in the picturesque landscapes of the Berkshires, our park offers a perfect retreat for nature enthusiasts, families, and adventure seekers alike. Explore the park's scenic trails, where you can enjoy hiking, birdwatching, and the breathtaking beauty of the surrounding forest. The park is named after its iconic geological feature, a massive boulder perched precariously atop a rock formation, which serves as a fascinating focal point for visitors.

Welcome to Mahanna Cobble Reserve Trailhead, your gateway to nature's serene beauty in Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, our park offers a tranquil escape for outdoor enthusiasts and families alike. Whether you're an avid hiker, a nature lover, or simply seeking a peaceful retreat, Mahanna Cobble Reserve Trailhead provides an array of scenic trails that wind through lush forests and offer breathtaking views of the surrounding landscape. Our well-maintained paths cater to all skill levels, ensuring an enjoyable experience for everyone. As you explore, you'll encounter diverse flora and fauna, adding to the park's vibrant ecosystem. Picnic areas are available for those who wish to relax and enjoy a meal amidst nature's splendor.

Welcome to The Boulders Reserve - Dalton Ave Trailhead, a serene and picturesque park located in the heart of Pittsfield, Massachusetts. Nestled on Dalton Avenue, this natural haven offers an escape into the great outdoors, perfect for nature enthusiasts and adventure seekers alike. Explore our extensive network of trails that meander through lush forests and rocky landscapes, providing an ideal setting for hiking, biking, and bird watching. Whether you're looking for a leisurely stroll or a challenging trek, our trails cater to all levels of outdoor enthusiasts.

Welcome to The Boulders Reserve, a serene and picturesque park located in the heart of Pittsfield, Massachusetts. Nestled in the scenic beauty of the Berkshires, The Boulders Reserve offers an idyllic escape into nature for both locals and visitors alike. Spanning a lush landscape, our park is renowned for its stunning rock formations, tranquil walking trails, and diverse wildlife. Whether you're seeking a peaceful retreat, an invigorating hike, or a family-friendly outing, The Boulders Reserve has something for everyone. Explore our well-maintained trails that wind through dense forests and open meadows, offering breathtaking views and ample opportunities for birdwatching and photography. Our park is also a perfect spot for picnicking, with several designated areas providing a relaxing setting for outdoor meals.