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Discovery Days

Timeless Traditions in the Berkshires

A Month of Magical Moments & Holiday Merriment
Lenox, MADec 1—30, 2025

Included with Your Stay

offers available

Timeless Traditions in the Berkshires

LenoxDec 1—30, 2025

Included with Your Stay

Book your event today

a woman enjoying the warmth of a fireplace and a hot drink

Timeless Traditions in the Berkshires

at Lenox, MA

Stay dates:

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Guests

Program

A Month of Magical Moments & Holiday Merriment

Price

Included with Your Stay

Offers availableContinue booking

Overview


Celebrate the magic of the season at our Lenox resort in the heart of the Berkshires. Throughout December, delight in candlelit yoga, gingerbread village building, cocoa-fueled trail walks, reflective talks, and festive concerts. Cozy campfires, seasonal rituals, and surprise experiences fill your days with warmth, joy, and connection. Let the charm of the Berkshires and the spirit of the holidays inspire you, nourish your body and mind, and create lasting memories.

Celebrate the magic of the season at our Lenox resort in the heart of the Berkshires. Throughout December, delight in candlelit yoga, gingerbread village building, cocoa-fueled trail walks, reflective talks, and festive concerts. Cozy campfires, seasonal rituals, and surprise experiences fill your days with warmth, joy, and connection. Let the charm of the Berkshires and the spirit of the holidays inspire you, nourish your body and mind, and create lasting memories.

The Program

An unforgettable experience designed just for you. 

Mon

Dec 01

Tue

Dec 02

Wed

Dec 03

Thu

Dec 04

Fri

Dec 05

9:30 AM - 12:00 PM
Stockbridge Holiday & History Walk 

Join Outdoor Sports guides for a 2+ mile walk from Stockbridge’s holiday decorated historic downtown to the town’s cemetery & discuss town history. Able walkers only, sturdy walking shoes required. Sign up: CR App or with a Wellness Guide, Ext. 55423.

Learn More
4:00 PM - 4:45 PM
Soothe and Surrender 

Embrace pausing and sink into cozy calm. Gentle supported restorative postures, soothing music, and the option for comforting essential oils help your body and mind unwind. Rest deeply and reconnect with peace, presence, and gratitude.

Learn More
7:00 PM - 7:50 PM
Peace On Earth Sound Bath 

A meditative sound experience to quiet the mind and open the heart. This holiday sound bath brings a sense of peace, grounding, and gentle joy for the season.

Learn More
9:00 AM - 5:00 PM
Jane Iredale Makeup Consults 

Join a Jane Iredale Expert for a personalized makeup consultation with tips on application, product recommendations, and techniques to enhance your natural beauty using skin-friendly products. Sign up: CR App or with a Wellness Guide, Ext 55423.

Learn More
9:30 AM - 10:00 AM
Advent Candle Lighting 

Join Holly Benzenhafer for an interspiritual candle lighting this Advent season. As we gather during the year's longest nights, we'll reflect on the themes of Hope, Peace, Love, and Joy - nurturing and celebrating our inner lights together.

Learn More
10:00 AM - 12:00 PM
Lenox Holiday & History Walk  

troll through Lenox’s holiday-decorated historic sites and learn the stories of the Berkshire Cottages, including Ventfort Hall and Springlawn. Stop at Lenox Coffee! Must be an able walker. Sign up via the CR App or with a Wellness Guide, Ext. 55423

4:00 PM - 4:45 PM
Soothe and Surrender 

Embrace pausing and sink into cozy calm. Gentle supported restorative postures, soothing music, and the option for comforting essential oils help your body and mind unwind. Rest deeply and reconnect with peace, presence, and gratitude.

Learn More
5:00 PM - 7:30 PM
Winterlights at Naumkeag in Stockbridge 

Experience the sparkle of Winterlights at Naumkeag in Stockbridge. Dazzling light displays, festive music, seasonal treats, and time outside among the trees and snow. Winter boots recommended. Sign-up: CR App or with a Wellness Guide, Ext. 55423

Learn More
9:30 AM - 12:00 PM
Stockbridge Holiday & History Walk 

Join Outdoor Sports guides for a 2+ mile walk from Stockbridge’s holiday decorated historic downtown to the town’s cemetery & discuss town history. Able walkers only, sturdy walking shoes required. Sign up: CR App or with a Wellness Guide, Ext. 55423.

Learn More
4:00 PM - 4:50 PM
Holiday Mocktails: Cheers to Wellbeing 

A hands-on demo where guests learn to craft holiday-themed mocktails.

5:00 PM - 6:00 PM
Full Moon Trailwalk & Hot Cocoa Campfire 

Soak up the moon glow during this on-property trail walk that ends at our outdoor firepit where you’ll warm up with hot cocoa. 

10:00 AM - 12:00 PM
Lenox Holiday & History Walk 

Stroll through Lenox’s holiday-decorated historic sites and learn the stories of the Berkshire Cottages, including Ventfort Hall and Springlawn. Stop at Lenox Coffee! Must be an able walker. Sign up via the CR App or with a Wellness Guide, Ext. 55423

2:00 PM - 2:50 PM
Seasonal Skincare: Winter Hydration 

Expert advice on the best way to maintain healthy, glowing skin this season. Learn how changing seasons affect your skin and the tools you can use to maintain a healthy glow all year long.

Learn More
4:00 PM - 4:30 PM
Advent Candle Lighting 

Join Holly Benzenhafer for an interspiritual candle lighting this Advent season. As we gather during the year's longest nights, we'll reflect on the themes of Hope, Peace, Love, and Joy - nurturing and celebrating our inner lights together.

Learn More
9:30 AM - 12:00 PM
Stockbridge Holiday & History Walk 

Join Outdoor Sports guides for a 2+ mile walk from Stockbridge’s holiday decorated historic downtown to the town’s cemetery & discuss town history. Able walkers only, sturdy walking shoes required. Sign up: CR App or with a Wellness Guide, Ext. 55423.

Learn More
4:00 PM - 4:45 PM
Soothe and Surrender 

Embrace pausing and sink into cozy calm. Gentle supported restorative postures, soothing music, and the option for comforting essential oils help your body and mind unwind. Rest deeply and reconnect with peace, presence, and gratitude.

Learn More
7:00 PM - 7:50 PM
Peace On Earth Sound Bath 

A meditative sound experience to quiet the mind and open the heart. This holiday sound bath brings a sense of peace, grounding, and gentle joy for the season.

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

Speakers


Special Offers

Book with a limited-time offer to make your stay even more rewarding.

Frequently Asked Questions


How do I attend this event?

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.

Do you have early check-in or late check-out?

You may arrive at 8 am; your room may not be ready until 3 pm. Pack exercise wear in a carry-on for a quick start. Meet with a Wellness Guide. Lunch is included with early arrival. Check-out of your room is at noon, however you can stay on the property until 5pm with lunch being the last meal.

What is your cancellation policy?

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.

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