Upcoming Events

Join us for an exhilarating exploration of the portion of the famed Appalachian Trail that snakes through the Berkshires. Stretching from Georgia to Maine, the trail is the longest hiking-only footpath in the world and a must-do for any outdoorsman.

Over the course of five days, our expert guides will lead daily hikes of six to 10 miles through this renowned natural area of Massachusetts. Seasoned outdoor experts from the Canyon Ranch Lenox team will share interesting facts about the trail and local history. Don't miss this one-of-a-kind opportunity.

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

Gray Simons, Outdoor Sports Guide, guides guests in a range of outdoor activities through all four seasons: hiking, biking, kayaking, canoeing, stand-up paddleboarding, cross-country skiing, snowshoeing, and more.

Wednesday, June 19

6 p.m. Adventures Along the Appalachian
In this opening session, Gray will share his expertise related to the hiking culture of New England. Learn facts about the Appalachian Trail and gain interesting insights before setting out on the trail this week.

Thursday, June 20

8 a.m.-3:30 p.m. Level 6 Hike: Connecticut Border to Guilder Pond
Strong climbs with magnificent views and rocky downhill sections. 8.6 miles. Lunch included.

Friday, June 21

8 a.m.-2:30 p.m. Level 5 Hike: Shay's Rebellion to Guilder Pond
Gentle rolling terrain to start, followed by a strenuous uphill climb where you'll be rewarded with vast, impressive views. 6.5 miles. Lunch included.

Saturday, June 22

8 a.m.-2:30 p.m. Level 4 Hike: June Mountain to East Mountain
A short steep ascent out of the Housatonic River Valley, including rolling sections along the historic Knox Trail. 7.6 miles. Lunch included.

Sunday, June 23

8 a.m.-3 p.m. Level 5 Hike: Pattison Road to Summit of Mount Greylock
Steep uphill hike from the reservoir to the summit of Mount Greylock, the highest peak in Massachusetts. 6 miles. Lunch included.