The Berkshires
Little Lion Inn is ideally located for exploring everything the Berkshires have to offer. Just minutes from Great Barrington and a short drive to Stockbridge, you’ll have easy access to hiking trails, local shops, art and culture, and some of the region’s best dining.
Whether you're here for a nature-filled getaway, a cultural escape, or simply a change of pace, Little Lion makes a perfect home base.
Outdoor Attractions
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From the 1,642-foot summit of this popular peak—which once drew 19th-century literary giants—gaze across the splendor of the Housatonic River Valley.
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The granddaddy of Berkshires hiking - Mount Greylock. Located in North County, the Berkshires’ primo natural landmark looms high above the surrounding Berkshire landscape reaching 3,491 feet. (Pet Friendly)
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The AT’s 2,000-mile trail cuts directly through the Berkshires over the top of Mt. Greylock and there are numerous entrances to the trail through the area, many connected off of local paths. (Pet Friendly)
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Bordering Washington, Becket, Lee and Lenox, October Mountain’s 16,500 acres is the largest state forest in Massachusetts offering trails for hiking, mountain biking and XC skiing and snowshoeing. (Pet Friendly)
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Best known for apples and the Furnace Brook Winery, Hilltop offers miles of groomed moderate and challenging terrain with separate trails specifically designed for snowshoeing. (Pet Friendly)
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This 11.2-mile former rail trail is an easy circuit for those looking for a less challenging bike path. This mostly flat surface runs from the Berkshire Mall in Pittsfield to Adams. (Pet Friendly)
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An exciting aerial forest adventure that provides a variety of courses that are fun for all ability levels. With 12 treetop courses of varying difficulties, you'll cross bridges and climb obstacles.
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Founded in 1895, this exclusive golf and tennis club is nestled in a tranquil mountain setting on the banks of the Housatonic River.
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This quiet, wooded 1.5-mile trail ascent winds through pines and hemlocks by Ice Glen (a glacial ravine) and ends at a summit tower with panoramic view of mountains in three surrounding states.
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A sprawling 1000-acre forest located in the town of Pittsfield, this year-round destination offers 30 miles of trails – many specifically marked for winter activity. It’s a pretty rustic set-up.
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A leader in outdoor adventure offering white water rafting in Massachusetts and Vermont, zip line canopy tours in the Berkshires, plus kayaking and canoeing trips.
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A tree-to-tree adventure destination, eight aerial obstacle courses meander through the trees at various heights and include 15-17 elements including high wires, zip lines, and rope ladders.
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Set amidst more than 1,000 lush acres, Pleasant Valley’s varied trails wind through forests, meadows, and wetlands along the slopes of Lenox Mountain.
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Stockbridge Bowl (Lake Mahkeenac) is a scenic 372-acre lake in Stockbridge, MA. It's a popular spot for boating, swimming, and enjoying the beautiful Berkshire views.
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View scenic woods, fields, and wetlands in this wildlife sanctuary which attracts warblers, turtles, ospreys and otters, at different times of year.
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The area’s most popular ski resort also offers an off season aerial adventure park, mountain biking and an adventure park with mountain coaster, zip line, alpine slide and scenic chairlift rides.
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One of the longest hikes in the Berkshires, the 10.5-mile Bear Mountain trail is an ambitious, all-day hike winding from Salisbury, CT to Sheffield, MA. Spectacular vistas of Bear and Race Mountains. (Pet Friendly)
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A pleasant surprise just minutes from historic Lenox, Kennedy Park is hardwood forest whose groomed trails snake their way through 502 acres of tree-lined forest.
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HomeFarm at Undermountain is a 501(c)3 nonprofit that commands a 95-acre property at 400 Undermountain Road in Lenox, Massachusetts. Overlooking the scenic Parsons Marsh, HomeFarm has historic farm buildings, working equestrian facilities such as stables and a large indoor riding arena, and grazing pastures. Discover the magic of the Berkshires on horseback.
Our guided trail rides and donkey treks offer a unique way to explore the landscape while connecting with our gentle rescue animals. Whether you're an experienced rider or a curious beginner, our programs invite you to slow down, ride mindfully, and savor the journey.
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“Quietwater” paddling means scenic canoeing or kayaking on lakes, ponds, and relatively calm rivers. Western Massachusetts has some splendid rivers and lakes for “quietwater”.
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With tubing on weekends and holidays, a terrain park, 1,000-foot vertical and 22 trails, this ski area, located in Great Barrington, appeals to little ones, novices and experts alike.
Our Sister Property, The Red Lion Inn
Little Lion Inn is a sister property to the historic Red Lion Inn in Stockbridge, a landmark destination known for its rich history and warm hospitality. Guests of Little Lion can easily enjoy the best of both experiences: modern simplicity paired with access to one of the Berkshires’ most iconic inns. From dining in the Main Dining Room or Widow Bingham’s Tavern to enjoying live music in the Lion’s Den, seasonal outdoor experiences, and classic New England charm, the Red Lion Inn offers an extension of your stay just a short drive away. It’s the perfect balance of laid-back, design-forward lodging and timeless Berkshire tradition.
Our Rooms & Amenities
Our guestrooms at Little Lion Inn offer a comfortable, design-forward stay in the Berkshires, blending retro-modern style with thoughtful amenities. Each room features plush bedding, modern conveniences, and inviting details designed for a relaxing and effortless experience. Guests enjoy easy, contactless check-in, pet-friendly accommodations, and access to nearby dining, shopping, and outdoor activities. Whether you're planning a weekend getaway in Great Barrington or an extended Berkshires stay, Little Lion Inn provides the perfect mix of comfort, convenience, and boutique charm.
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