If you are a city-dweller seeking a peaceful walk in the woods and a bit of fresh air, make sure to visit Pleasant Valley Wildlife Sanctuary – a property of Mass Audubon. With miles of extensive trails through a 1300 acre wilderness, it offers views, forests, wetlands, rare species, and terrain both friendly and challenging for walkers and hikers.

Kennedy Park – a town conservation property for miles of trails – is easily accessed from downtown Lenox by a moderate walk up past the Church on the Hill or via trail access from the Arcadian Shop parking lot. Trails here are open to dogs, mountain bikes, XC Skiers and snowshoers in the winter and is a great place for a traffic-free run. Maps are available at the Lenox Visitors Center.

Looking to get on the water? The Housatonic is a winding water walkway that twists itself around the Berkshires. Grab a friend and call ahead to the Arcadian Shop in Lenox. They’ll deliver two kayaks to Decker’s Landing and pick you up at Woods Pond after a few hours of paddling on the Housatonic and reconnecting with nature.

Want to climb to the stars? At 3,491 feet, Mt. Greylock is the highest peak in the state. With more than 50 miles of hiking trails and most summit trails with 2,000+ foot ascents, Mt. Greylock State Reservation ranks up there with any hiking destination in the Northeast. However, unlike many high peaks in the northeast, Mt. Greylock’s summit is also home to a rustic 1930’s lodge constructed by the Civilian Conservation Corps. You can even sleep and eat there!

Lenox Tree Crawl Camps & EducationHealth and WellnessOutdoors

Lenox Tree Crawl

The Lenox Tree Crawl, sponsored by the Lenox Land Trust, is a permanent exhibit for the town of Lenox for locals and visitors. People can learn more about the amazing trees that make our town so beautiful, year round. The Tree Crawl is free and open to everyone. The trees, permanently tagged with QR codes,…
Lenox Loves Music! Arts & CultureOutdoorsThings To Do

Lenox Loves Music!

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High Lawn Farm DessertsFoodOutdoorsRestaurantsSpecialty Foods and Beverages

High Lawn Farm

highlawnfarm.com 535 Summer Street, Lee, MA 01238 (413) 243-0627 Ext. 112 / mail@highlawnfarm.com A historic family-owned dairy farm located in the beautiful rolling Berkshire hills. Visit their Farmstead Creamery Shop open 7 days a week, where they offer farm-fresh artisanal cheese, butter, ice cream, and more made with pure Jersey cow’s milk. Enjoy an ice cream…
Homefarm at Undermountain Camps & EducationOutdoorsThings To Do

Homefarm at Undermountain

homefarmundermountain.org P.O. Box 733, 400 Undermountain Road, Lenox, MA 01240 413.637.3365 Year-round riding is a pleasure at HomeFarm at Undermountain -whether you are riding in the protection of our spacious indoor arena, or happily trotting through lovely fields and woods, we encourage all levels of ability to enjoy the equestrian life at HomeFarm at Undermountain.…
Arcadian Shop OutdoorsShoppingThings To Do

Arcadian Shop

arcadian.com 91 Pittsfield Road, Lenox, MA 01240 413.637.3010 • info@arcadian.com Established in 1974 The Arcadian Shop has been a leader in the outdoor industry since 1974.  We specialize in a variety of outdoor pursuits including biking, hiking, camping, kayaking, paddle boarding, running, climbing, snowshoeing, x-country, alpine touring and telemark skiing just to name a few.  We also offer…
Tanglewood Arts & CultureOutdoorsThings To Do

Tanglewood

tanglewood.org 297 West Street, Lenox, MA 01240 Information: 413.637.1600 Tickets: 888.266.1200 Join the Boston Symphony Orchestra at Tanglewood Music Center, their idyllic summer home in the Berkshires! Tanglewood is one of the world's most beloved music festivals, with an annual music series showcasing classical, pop and contemporary artists, and has been setting the standard for…
Norman Rockwell Museum Arts & CultureOutdoorsThings To Do

Norman Rockwell Museum

nrm.org 9 Glendale Road, Route 183, Stockbridge, MA 01262 413.298.4100 • questions@nrm.org Set in the artist’s hometown, housing the world’s largest collection of Norman Rockwell’s original art & the works of other contemporary & past masters. Open year-round. Rockwell’s Stockbridge studio & Terrace Café open May-Oct.  
Lilac Park OutdoorsThings To Do

Lilac Park

Main Street, Lenox, MA 01240 Town picnic and park, restored by the Lenox Garden Club to its original collection of named varieties of lilacs. Enjoy evening Concerts in the Park during the summer.
Kennedy Park OutdoorsThings To Do

Kennedy Park

Route 7 and 20, Pittsfield Road, Lenox, MA 01240 Town-owned & maintained hardwood forest with old carriage roads & nearly 15 miles of groomed trails, with a lookout point of a mountain vista. Ideal for hiking, picnics, & cross-country skiing. Trailhead access via Main Street, next to Church on the Hill, in Lenox town center,…