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Appalachian Trail Hiking

Adventure outdoors in the Berkshires
Lenox, MASep 15—21, 2025

Included with Your Stay

offers available

Appalachian Trail Hiking

Sep 15—21, 2025

Included with Your Stay

Book your event today

Appalachian Trail Hiking

at Lenox, MA

Number of nights:

6 nights

Stay dates

Sep 15—21, 2025 (6 nights)

Guests

Program

Adventure outdoors in the Berkshires

Price

Included with Your Stay

Offers availableContinue booking

Overview

In this fantastic workout for mind and body, you’ll see spectacular streams, meadows, lakes and wildlife, and learn about the area’s fascinating history during this unique hiking retreat. Over the course of seven 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 this fantastic workout for mind and body, you’ll see spectacular streams, meadows, lakes and wildlife, and learn about the area’s fascinating history during this unique hiking retreat. Over the course of seven 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.

The Program

An unforgettable experience designed just for you. 

Mon

Sep 15

Tue

Sep 16

Wed

Sep 17

Thu

Sep 18

Fri

Sep 19

8:00 AM - 4:00 PM
Hike: Level 5 – AT to VT & the Pine Cobble 

The northernmost part of the Appalachian Trail in Massachusetts begins by crossing the Hoosac River. Then up to East Mountain and the Vermont border. Double back to Pine Cobble and descend into Williamstown. 6 miles. 1,100 ft. vertical rise. Sign up: CR App or with a Wellness Guide, Ext. 55423.

8:00 AM - 4:30 PM
Hike: Level 5 - Reynold's Rock over Mount Greylock 

Rolling terrain up to Saddle Ball Mountain followed by steep miles up Massachusetts’ highest peak. 8 miles. Lunch included.

8:00 AM - 2:30 PM
Hike: Level 5 – Shay's Rebellion to Guilder Pond 

Gentle rolling terrain to start. Strenuous uphill climb rewarded by vast, impressive views. 6.5 miles. Lunch included.

8:00 AM - 2:30 PM
Hike: Level 5 - Wilcox to Fernside 

A beautiful and rocky section featuring Benedict Pond and the county’s most impressive beaver dam. Hike ends at a Shaker Village in the hamlet of Tyringham. 8.1 miles. Vertical rise 2,000ft. Sign up: CR App or with a Wellness Guide, Ext. 55423.

8:00 AM - 2:30 PM
Hike: Level 4 - Boulders to Cheshire Cobble 

Enjoy a moderate climb through hardwoods to outstanding views from the cobble. Rolling forest miles to the village and the famous Cheshire Mammoth Cheese monument! 7 miles. Vertical rise 1,300ft. Sign up: CR App or with a Wellness Guide, Ext. 55423.

8:00 AM - 4:00 PM
Hike: Level 5 – AT to VT & the Pine Cobble 

The northernmost part of the Appalachian Trail in Massachusetts begins by crossing the Hoosac River. Then up to East Mountain and the Vermont border. Double back to Pine Cobble and descend into Williamstown. 6 miles. 1,100 ft. vertical rise. Sign up: CR App or with a Wellness Guide, Ext. 55423.

Always Included

Savor unlimited meals, snacks, and beverages at our on-site restaurants, each offering nourishing, seasonal dishes made with fresh ingredients.

EXPLORE DINING
Always Included Meals LenoxAlways Included Meals Lenox

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