Discovery Days

Waterfalls and Wildflower Hiking Week

Explore Spring Landscapes Shaped by Rain and Snowmelt
Lenox, MAMay 11—17, 2026

Included with Your Stay

Companion Rate Available

offers available

Waterfalls and Wildflower Hiking Week

LenoxMay 11—17, 2026
Included with Your StayCompanion Rate Available

Book your event today

Walk Among the Waterfalls - event

Waterfalls and Wildflower Hiking Week

at Lenox, MA

Stay dates:

Guests

Program

Explore Spring Landscapes Shaped by Rain and Snowmelt

Price

Included with Your Stay

Companion Rate Available

Offers availableContinue booking

Overview


Walk among cascading waterfalls and spring-fed trails during this immersive hiking week in the Berkshires. Guided hikes cover terrain shaped by seasonal rain and snowmelt, with routes designed for a range of fitness levels. As you move through forests and alongside flowing water, you’ll experience the calming effects of nature while building confidence, endurance, and connection outdoors.

Walk among cascading waterfalls and spring-fed trails during this immersive hiking week in the Berkshires. Guided hikes cover terrain shaped by seasonal rain and snowmelt, with routes designed for a range of fitness levels. As you move through forests and alongside flowing water, you’ll experience the calming effects of nature while building confidence, endurance, and connection outdoors.

The Program

An unforgettable experience designed just for you. 

Mon

May 11

Tue

May 12

Wed

May 13

Thu

May 14

Fri

May 15

8:00 AM - 2:00 PM
Hike: Level 4 - Keystone Arches to Glendale Falls 

Enjoy moderate climbs and rocky woodland terrain at this historic granite quarry. Then, jump in the van, and take a short trip to explore and hike at Massachusetts’ largest waterfall. Lunch included. 6 miles. 1,000ft vertical rise.

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9:00 AM - 12:00 PM
Hike: Level 3 - Monument Mountain 

Steady ascent with a rock scramble at the top. Great views! Steep Descent. 2.5 miles. 827ft vertical rise.

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1:30 PM - 3:30 PM
Hike: Level 2 - Steven’s Glen 

Steep descent to a waterfall, then moderate ascent back out of the glen.

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8:00 AM - 3:00 PM
Hike: Level 5 - Bash Bish Falls 

Moderate ascent, then a rolling ridge with sweeping views. Followed by a very steep descent with high drops to a spectacular waterfall. Lunch included. 8 miles. 1,230ft Vertical rise. Sign up: CR App or with a Wellness Guide, Ext. 55423.

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9:00 AM - 12:00 PM
Hike: Level 3 - Gorge Trail at October Mtn. 

Short but steep uphill along a river to a mountain lake and back. 3 miles. 600ft vertical rise.

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1:30 PM - 3:30 PM
Hike: Level 1 - Gould Meadows 

This gentle hike takes you along the shores of the beautiful Stockbridge Bowl, and through the surrounding forest and meadows. Underfoot you will experience grassy paths and rooty trails. Sign up: CR App or with a Wellness Guide, Ext. 55423

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4:00 PM - 4:50 PM
Walking Labyrinth Meditation 

Join us in a slow, guided walk along the path of the labyrinth to experience how it can be a powerful meditation tool

8:00 AM - 2:00 PM
Hike: Level 4 - Sanderson Falls 

A steep ascent on this loop hike leads to an expansive view of the eastern edges of Berkshire County and one of the headwaters of the Westfield River. Rolling terrain through reclaimed farmland brings you to Sanderson Brook Falls. 4.4 miles. Vertical rise 1,133 ft. Sign up: CR App or with a Wellness Guide, Ext. 55423

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9:00 AM - 12:00 PM
Hike: Level 3 - Lulu Cascade 

Moderate ascent with rocky terrain. Beautiful cascading water. Nice intermediate hike. 4.5 miles. 1,165ft vertical rise.

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2:00 PM - 4:00 PM
Hike: Level 2 - Katie’s Big Ash Trail 

Enjoy a scenic hike, passing by old oak trees and walking alongside a flowing stream. Rolling terrain with a steep incline.

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8:00 AM - 2:30 PM
Hike: Level 5 - Race Brook Falls 

A very steep, rocky ascent to the ridge, then rolling until another steep, rocky climb to the summit of Mt. Everett. Lunch included. 6.5 miles. 2,000ft vertical rise.

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9:00 AM - 12:00 PM
Hike: Level 2+ - Basin Pond 

Enjoy this scenic woodland hike on rocky, rolling trails and over several babbling brooks. 4 miles. 902ft vertical rise.

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1:30 PM - 3:30 PM
Hike: Level 1 - Pleasant Valley Beaver Ponds 

A leisurely hike on flat, mildly rolling wooded trails past several beaver ponds.

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8:00 AM - 1:30 PM
Hike: Level 4 - Money Brook 

Steady uphill hike, including a few stream crossings and rocky terrain. Savor lunch beside the falls. Reverse your footsteps down the valley while traversing beautiful brooks. Lunch included. 6 miles. 1,800ft vertical rise.

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9:00 AM - 12:00 PM
Hike: Level 3 - Pleasant Valley Overbrook Trail 

Steady, moderate ascent to the summit of Lenox Mountain and down again. 3 miles. 820ft vertical rise

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2:00 PM - 4:00 PM
Hike: Level 2 - Steven’s Glen 

Steep descent to a waterfall, then moderate ascent back out of the glen.

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8:00 AM - 2:00 PM
Hike: Level 4 - Keystone Arches to Glendale Falls 

Enjoy moderate climbs and rocky woodland terrain at this historic granite quarry. Then, jump in the van, and take a short trip to explore and hike at Massachusetts’ largest waterfall. Lunch included. 6 miles. 1,000ft vertical rise.

Learn More
9:00 AM - 12:00 PM
Hike: Level 3 - Monument Mountain 

Steady ascent with a rock scramble at the top. Great views! Steep Descent. 2.5 miles. 827ft vertical rise.

Learn More
1:30 PM - 3:30 PM
Hike: Level 2 - Steven’s Glen 

Steep descent to a waterfall, then moderate ascent back out of the glen.

Learn More

Always Included

When you want it all taken care of, it matters where you stay.

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

EXPLORE DINING
All-Inclusive Chef-Crafted DiningAll-Inclusive Chef-Crafted Dining

Frequently Asked Questions


This special event is open to all resort guests. You can come for two days, or stay all week and enjoy the programming featured in this event as part of your all-inclusive stay.

To get the most enjoyment from this event, we recommend you come on our Personal Discovery Designed Experience, which includes your choice from up to 35 of our guest-favorite services daily.

The spa is the beating heart of Canyon Ranch resorts. It is where you will attend fitness classes, receive services, or just luxuriate in our relaxing facilities. Each fully attended, gender-specific locker room includes luxurious showers, steam rooms, saunas, whirlpools, cryo-plunge pools, and relaxation areas.

Our standard policy requires a two-night deposit at the time of booking, fully refundable up to 21 days before arrival; deposit is forfeited with less than 21 days’ notice.