Outdoor Activities

Little Lion Inn is your perfect home base for outdoor adventures in the Berkshires. Located just minutes from Monument Mountain, guests can enjoy scenic hiking trails, breathtaking summit views, and peaceful nature walks right across the street. The surrounding area also offers easy access to biking routes, kayaking, skiing, and year-round exploration of the region’s natural beauty.

Outdoor Activities

Sunset over a mountainous landscape with forests and rocky ledge in the foreground

  • 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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A white lighthouse standing on a grassy hill with a gravel path leading up to it, under a blue sky with scattered white clouds.

  • 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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Trail sign for Appalachian Trail Northbound with directions and distance to Old Trail.

  • 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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Three people kayaking on a calm river surrounded by colorful autumn trees.

  • 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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A girl picking apples from an apple tree in an orchard during daytime.

  • 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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A scenic view of Ashwulitcoock Rail Trail with a wooden fence, trees in fall foliage, and a lake in the background on a clear day.

  • 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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Children and adults walking on a rope bridge and platform course in a forested adventure park surrounded by tall trees and lush green leaves.

  • 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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A scenic park view with a bridge over a pond, green grass, tall trees, and a house in the background under a blue sky.

  • 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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A person walking on a dirt trail through a wooded forest with rocks and trees covered in moss.

  • 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 serene lake with trees and greenery surrounding it, clear blue sky overhead, and a sign in the foreground indicating "Hubbard Pond".

  • 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 group of six people smiling and paddling in an inflatable raft through a river with rocks and greenery, wearing helmets and life jackets.

  • 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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People at an outdoor adventure park in a forest, with wooden climbing structures and platforms among tall trees, and individuals wearing safety gear, including helmets.

  • 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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Person hitting a golf ball on a lush golf course with trees in the background.

  • Located in Lanesborough, this is one of the Berkshire’s most unique public golf courses with spectacular views on a championship layout.

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A wooden bridge over a lake surrounded by colorful autumn trees.

  • 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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Two people paddleboarding on a calm lake surrounded by trees and rolling green hills.

  • 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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A river flowing through a forested area with autumn foliage, distant mountains, and a partly cloudy sky.

  • 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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A family of five standing on snow with skis and poles, dressed in winter gear including helmets and goggles, on a snowy mountain with a cloudy sky.

  • 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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Two people walking on a golf course, carrying golf bags, with a lush green background and trees.

  • An 18-hole course with character, incredible greens and spectacular views! Open to the public. Affordable golf at its best.

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Group of children with backpacks hiking on a wooded trail, with one child holding a walking stick.

  • 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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Sunset over a mountain range viewed from a park with benches and trees in the foreground.

  • 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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Person riding a horse through a grassy field with trees in the background on a sunny day.

  • 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.

Three people kayaking on calm water during the day, with trees visible in the background.

  • “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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Skier descending a snowy slope in a forested area with other skiers and a ski lift in the background.

  • 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.

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Four golfers walking on the golf course with golf bags, approaching a green and sand trap, during a sunny day.

  • Picturesque 18-hole, premier course in the central Berkshires. Excellent conditions. Challenging play. Titleist rentals. Lessons. Range. Pub.

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Front porch of a white house with a red door, decorated with black and white chairs, potted plants, trees, and hanging flower baskets.

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.

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A couple sitting on a park bench with their dog, surrounded by greenery, smiling at each other, with large open grassy area and trees in the background.
A bedroom with a bed featuring an orange headboard, white bedding, and pillows. There are two bedside tables, one with a small clock. A framed picture hangs above the bed. To the right, there is a standing red lamp, a small closet, and a window with white curtains. Two gray armchairs and a small table with magazines are near the window, with an air conditioning unit below.
A bedroom with a bed covered in white bedding and pillows, a white nightstand with a lamp, a mirror on the wall, and blue curtains over a window.
A fluffy brown dog with a colorful bandana sitting on a wooden park bench, smiling with its tongue out, next to a person in a light-colored shirt whose face is not visible, outdoors in a park with green trees and a building in the background.
Two beds in a warmly lit hotel room with a stone accent wall, framed artwork, and windows with curtains, one showing greenery outside.

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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