TOP 30 Hiking destination in Lenox, Massachusetts

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Stonover Farm is a charming lodging institution located at 169 Under Mountain Road in Lenox, Massachusetts, United States. Surrounded by picturesque countryside, this tranquil farm offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. The property features beautifully appointed rooms, a cozy fireplace, and stunning views of the rolling hills. Guests can enjoy a relaxing stay in this idyllic setting, with opportunities for hiking, biking, and exploring the nearby attractions. Whether you're seeking a romantic getaway or a peaceful weekend retreat, Stonover Farm provides a warm and welcoming atmosphere for a memorable stay.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

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.

Arcadian Shop is a premier destination for outdoor enthusiasts located at 91 Pittsfield Road in Lenox, Massachusetts. This multi-faceted institution serves as a top-notch bicycle store, clothing store, shoe store, and general outdoor gear store all in one. With a wide selection of high-quality products and knowledgeable staff, Arcadian Shop is the go-to spot for all your outdoor adventure needs. Whether you're in need of a new bike, hiking boots, or the latest outdoor apparel, Arcadian Shop has you covered. Visit us today and gear up for your next outdoor excursion!

Welcome to Stevens Glen Trail Head, a serene and picturesque park located in the heart of the Berkshires at Lenox Road, West Stockbridge, Massachusetts. Nestled in the lush greenery of Richmond, MA, our park offers a tranquil escape for nature lovers and outdoor enthusiasts. Stevens Glen Trail Head is renowned for its breathtaking landscapes, featuring well-maintained trails that wind through dense forests, alongside babbling brooks, and past stunning waterfalls. Whether you're a seasoned hiker or just looking for a peaceful walk in nature, our trails cater to all skill levels, providing a perfect opportunity to reconnect with the great outdoors.

Welcome to Kennedy Park, a serene oasis nestled in the heart of Lenox, Massachusetts. Located at 275 Main Street, this enchanting park offers a perfect blend of natural beauty and outdoor adventure, making it an ideal destination for both locals and tourists alike. Spanning over 500 acres, Kennedy Park is a haven for nature enthusiasts, offering a network of well-maintained trails perfect for hiking, biking, and cross-country skiing. Immerse yourself in the lush landscapes and enjoy the stunning vistas that change with the seasons, from vibrant spring blooms to the rich tapestry of fall foliage. Whether you're seeking a peaceful stroll, a family picnic, or an invigorating outdoor workout, Kennedy Park provides a picturesque setting for all your recreational needs.

Welcome to Kennedy Park, a serene natural retreat located at 18 Evergreen Trail in the picturesque town of Lenox, Massachusetts. Spanning over 500 acres, Kennedy Park offers a perfect escape for nature lovers, outdoor enthusiasts, and families alike. Immerse yourself in the beauty of New England's landscapes as you explore our extensive network of trails, ideal for hiking, mountain biking, and cross-country skiing in the winter months. The park is home to diverse flora and fauna, providing a peaceful sanctuary for wildlife observation and photography. With its well-maintained paths and scenic vistas, Kennedy Park is a favorite destination for both locals and visitors seeking tranquility and adventure in the heart of the Berkshires.

Welcome to Chester Granite and Polishing Works, a historic gem nestled in the heart of Chester Factory Village at 7 Prospect Street, Chester, Massachusetts. This unique park, recently acquired by the Western Mass Hilltown Hikers, a dedicated 501(c)(3) organization, is a testament to the region's rich industrial past and natural beauty. Originally established in the early 1800s, the Granite Works played a pivotal role in the local industry, cutting and finishing granite sourced from the nearby Beckett Quarry. Visitors can marvel at the historic granite saw, once powered by steam, and the ingenious mechanisms designed to handle massive stone blocks. Thanks to the efforts of the Hilltown Hikers, this remarkable site has been preserved for future generations, preventing its loss to history.

Welcome to Western Mass Hilltown Hikers, your gateway to the breathtaking beauty and rich history of the Hilltowns in Western Massachusetts. Located on Round Hill Road in Chester, MA, our park and hiking group is dedicated to preserving and promoting the natural and historical treasures of this unique region for all to enjoy. In an exciting development, the Western Mass Hilltown Hikers recently acquired the historic Chester Hudson and Granite Works property. This landmark, near the old Chester Railway Station, dates back to the early 1800s and was pivotal in the granite industry, with its impressive granite saw and mechanisms originally powered by steam. Thanks to our dedicated efforts, this piece of history will be preserved for future generations, with plans to apply for National Historic Landmark status.

Welcome to Great Barrington Resort House, your serene getaway nestled in the picturesque landscapes of Lenox, Massachusetts. Located at the heart of the Berkshires, our resort offers a perfect blend of luxury, comfort, and natural beauty. Whether you're seeking a peaceful retreat or an adventure-filled vacation, our resort is the ideal destination. At Great Barrington Resort House, we pride ourselves on providing exceptional hospitality and personalized service. Our elegantly designed rooms and suites offer breathtaking views and modern amenities to ensure a relaxing stay. Enjoy gourmet dining at our on-site restaurant, unwind at our spa, or take a dip in our heated pool.