The Berkshires become a magical place when winter transforms the area into a snow-covered wonderland. The charming fall festivals and leaf-peeping trips give way to twinkling light displays and exhilarating outdoor adventures. To make the most of the best winter activities the Berkshires have to offer, visit one of our Canna Provisions dispensaries to pick up some high-quality cannabis products.

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Things to Do in the Berkshires in Winter

1. Winterlights at Naumkeag: A Stockbridge Tradition

Naumkeag is a Gilded Age estate in Stockbridge. Each December, the estate transforms into an enchanted winter paradise as its Winterlights Festival begins. As you stroll through the beautiful gardens and grounds, you’ll see thousands of twinkling lights that create a storybook atmosphere. 

To stay warm, take advantage of the complimentary hot cider and cocoa. To enhance your appreciation of this dazzling display, consider having a puff or two of Super Sour Diesel sativa vape before you head out.

2. Stockbridge Main Street at Christmas: Norman Rockwell Come to Life

A walk down Stockbridge’s Main Street during its Christmas celebration feels like stepping into a Norman Rockwell painting. This historic streetscape becomes adorned with wreaths, lights, and festive decorations, fully embodying classic New England charm. 

Local shops and galleries along the street greet visitors with seasonal displays, while the Norman Rockwell Museum offers special exhibitions to celebrate the artist’s famous depictions of American life.

3. NightWood at The Mount: Edith Wharton’s Estate Illuminated

Each winter, The Mount, novelist Edith Wharton’s stunning estate in Lenox, hosts the spectacular NightWood event. To celebrate the holidays, the estate’s grounds come alive with artistic light installations. Cinematic music and scenic elements combine with beautifully placed lights to create an unforgettable evening walk. The contrast between modern lighting and the estate’s classic design makes it a must-see destination for culture enthusiasts. 

Winter Activities for Every Interest

4. Ice Skating Across the Berkshires

The Fitzpatrick Skating Rink in Holyoke provides easy access to ice skating for both residents and visitors. The rink is managed by the Department of Conservation and Recreation. This indoor rink is perfect for enjoying some winter fun without battling the snow. There are also several outdoor rinks in various Berkshire towns, each offering its own unique charm. 

5. Winter Festivals Berkshires & Seasonal Markets

Communities in the Berkshires love to celebrate the holidays. During the winter months, you’ll find no shortage of artisan craft fairs and holiday markets that showcase the region’s creative spirit. These events provide a wonderful opportunity to mingle with both locals and fellow travelers while enjoying the friendly atmosphere that Berkshire communities are known for.

6. Cozy Indoor Experiences & Cultural Events

In the colder months, the warmth of the indoors is often a welcome feeling. MASS MoCA is one of the largest contemporary art museums in the country, housed in a 19th-century factory campus. Its expansive galleries will provide hours of warm indoor exploration.

Meanwhile, the Canyon Ranch in Lenox offers day packages that provide a perfect winter escape. There, you’ll find spa services like facials, massages, and energy therapies. For those looking for something a little longer, you’ll also find some of the coziest accommodations in the region, along with five-star dining opportunities.

Winter Activities Near Holyoke & Lee

7. Close-to-Home Winter Fun for Locals

Both Holyoke and Lee serve as excellent home bases for winter exploration. Holyoke offers easy access to Mount Tom, which presents visitors with many opportunities for snowshoeing and winter hiking while taking in the valley’s stunning views.

Lee’s location in the heart of the Berkshires puts downtown Stockbridge and Lenox within a short drive. Both towns offer cozy restaurants and cafes that are perfect for warming up after outdoor adventures.

8. Day Trip Destinations from Both Canna Provisions Locations

Each of our Canna Provisions locations is within easy driving distance of the region’s top winter destinations. Jiminy Peak Mountain Resort in Hancock offers skiing and snowboarding across 45 trails, plus a mountain coaster, tubing park, and snowshoeing trails. You can also easily reach the charming villages of Great Barrington and Sheffield. These locations offer unique winter activities, dining, and shopping experiences.

Plan Your Berkshires Winter Adventure With Canna Provisions

As you plan your Berkshires winter experience, be sure to make Canna Provisions a part of your plans. Our dispensaries in Holyoke and Lee offer premium cannabis grown by Massachusetts’ finest cultivators. You’ll also find an array of edibles, concentrates, vapes, and everything else you need to enhance your winter excursions. 

Whether you need to energize yourself for the day ahead or wind down after a long adventure, you’ll find what you need on the shelves of Canna Provisions. If you’re in a hurry, order ahead through our online menu, and we’ll have your products ready when you arrive.

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