Upcoming Events

Discover the lively, charming region of the Berkshires, home to a vibrant cultural scene, historic landmarks, and some of the most scenic hikes in the Northeast.

Our expert outdoor guides will treat you to five days full of their "best of the best," a curated itinerary of hikes, history walks, and more. Enjoy 360-degree views from the inspiring Monument Mountain, hike a rolling ridgeline to the highest point in Massachusetts, visit one of North America's southernmost occurrences of boreal forests, and spend an evening at world-renowned venues like Tanglewood and Jacob's Pillow.

Don't miss this exclusive opportunity to explore one of New England's most beautiful regions during one of its best times of the year.

In addition to this event, you can enjoy all of the daily activities that Lenox, MA offers. Explore our sample schedule.

Monday, August 12

8 a.m.-2:30 p.m. Level 5 Hike from Sage’s Ravine to Eagle’s Perch
Explore the enchanting Sage’s Ravine, a steep valley cut by a stream that winds through the forest. Ascend to Bear Rock Falls’ primitive camping area and Eagle’s Perch for some wonderful views.

9:15 a.m.-12:45 p.m. Canoe-Hike Combo
Our outdoor guides will lead you on a Level 2 hike on the Appalachian Trail followed by a canoe ride on Goose Pond.

1:30-3:30 p.m. Level 3 Bike Ride Up Golden Hill
Enjoy a road bike ride through our neighboring town of Lenox Dale. After a warm-up and overview, this ride covers rolling ups and downs through Lenox Dale along the Housatonic River and back to Lenox.

6-8 p.m. Evening Observation Trail Walk
Traverse the valley that runs through our local Massachusetts Audubon Sanctuary. Travel woodland trails, bridges, and boardwalks. Guides will share their knowledge of how local wildlife supports and affects the forest ecology.

Tuesday, August 13

7-9 a.m. Stand-Up Paddle Board
Learn the basics of stand-up paddle boarding while soaking up the unique beauty of the Berkshires.

9:15 a.m.-12:15 p.m. Level 3 Hike to Monument Mountain
Enjoy a steady ascent with a rock scramble at the top and great views.

10 a.m.-Noon Lenox History Walk
Take a walking tour of Lenox’s historic sites. Learn the history, legends, and current status of Berkshire Cottages, including Ventfort Hall and Springlawn.

1:15-3:15 p.m. Level 1 Hike to Gould Meadows

1:30-3:30 p.m. Level 3 Bike Ride to Get Ice Cream At High Lawn
Take a hilly ride to get homemade ice cream at High Lawn Farm, a family-owned, 100-percent Jersey dairy farm. Midway through, we’ll stop at their creamery for farm-fresh ice cream.

4-7 p.m. Level 2 Hike to Tyringham Cobble
The Tyringham Valley offers beautiful rolling meadows, rocky outcroppings, and a storied history. Enjoy a stroll through the meadows to the top of the cobble for three distinct valley views.

Wednesday, August 14

8 a.m.-2:30 p.m. Level 5 Hike to Jones' Nose at Mount Greylock
Ascend to the highest point in Massachusetts, then connect with the Appalachian Trail to enjoy expansive views from the summit of Mount Greylock.

1:15-3:45 p.m. Level 2 Hike to Ice Glen and Laura’s Tower
Explore Ice Glen, a deep ravine surrounded by old-growth hemlock trees and filled with giant glacial erratics that can hold snow and ice into the summer months. We'll then ascend to Laura’s Tower, before reversing back down.

6-8 p.m. Evening Kayaking at Stockbridge Bowl
Enjoy a sunset kayaking tour.

Thursday, August 15

7-9 a.m. Stand-Up Paddle Boarding
Learn the basics of stand-up paddle boarding while soaking up the unique beauty of the Berkshires.

8:15 a.m.-12:15 p.m. Level 2 Bike Ride Along Ashuwillticook Rail Trail
Join our guides on a beginner-intermediate ride as we explore the former railroad corridor that runs parallel to Route 8.

10 a.m.-12:30 p.m. Stockbridge History Walk
Join outdoor sports guides for a more than two mile walk from Stockbridge’s historic downtown to the town’s cemetery as we discuss the local history.

1:15-3:15 p.m. Level 1 Hike to Kennedy Park Gazebo
Visit the former site of the Aspinwall Hotel, lost to a fire in 1931. The forest opens to a maintained picnic area and a view of Lenox and Tanglewood before wooded trails take us to the Gazebo.

1:30-3:30 p.m. Shinrin Yoku at The Mount
Experience the Japanese practice of taking in the forest atmosphere, or “forest bathing” at the historic house museum, The Mount. Join your guide on a slow, intentional walk into the woods to de-stress and reconnect with nature.

Friday, August 16

7-9 a.m. Kayaking
Enjoy a kayak tour on one of our beautiful local lakes. Instruction included. Must be an able swimmer. Weather dependent.

8 a.m.-2:30 p.m. Level 5 Hike to Haley Farm and Deer Run
Advanced hike with the two best views in the Berkshires, cascading streams and falls, heart-pumping climbs, and leg-burning descents. Steep, rocky climbs, and dramatic views of Mount Greylock.

1:30-3:30 p.m. Level 3 Gravel Grinder Bike Ride at Wood’s Pond
Enjoy a secluded ride featuring rolling carriage roads, gravel, paved, and dirt sections. This ride utilizes our mountain bike fleet on the picturesque backroads of Berkshire County.

6-8 p.m. Evening Kayaking at Stockbridge Bowl
Enjoy a sunset kayak tour. Instruction included. Must be an able swimmer. Weather dependent.