5 Fun Holiday Activities in the Berkshires

Winter Holiday Activities in the Berkshires!

It’s that wonderful time of year, when thoughts turn to family or fun, or both! When you live in a winter wonderland like we do in the Berkshires, you want to be able to get out and enjoy it. We’ve got a list of 5 fun holiday activities around the Berkshires for you to do when you stay with us at Devonfield Inn. Take a look, figure out your itinerary, and get ready to enjoy the glory of a Massachusetts mid-winter!


Berkshire Holiday things to do - horseriding, holiday lights, room with fireplace

1. Holiday Winterlights at Naumkeag

In first place is the most excellent Winterlights at Naumkeag – a beautiful display of holiday magic at the gorgeous Naumkeag Estate in Stockbridge. The whole family can enjoy this event, or hold hands and cuddle with your sweetie while you wander under the thousands of glittering lights at this lovely Gilded Age estate, featuring a rare “Berkshire Cottage”. Advanced tickets are required – Register here.
Friday, November 27, 2020 – January 2, 2021
One hour reservations starting at 4:30pm, Final reservation at 7:45pm
5 Prospect Hill Rd, Stockbridge, MA 01262

2. Hancock Holidays

A beloved annual tradition for all ages in Hancock Shaker Village. Take part in cookie decorating and ornament making workshops, artisan demonstrations, Shaker talks, caroling, a gingerbread contest, a visit with the animals in the barn, and more. Most activities included with admission, but a small fee applies for a few.

– Hancock Holidays – Saturday, December 12, 2020, 10am – 4pm
– Admission is $20 for adults, $8 ages 13–17, and free for children 12 and under.

3. Hancock Hibernation Celebration

On December 31, ring out 2020 with artist demonstrations, Shaker Winter Tales, and s’mores over an open fire. New for 2020 – a Tree of Hope, so you can write a wish for 2021 and hang it on the tree.

– Hibernation Celebration – Thursday, December 31, 2020, 10am – 4pm
– 1843 West Housatonic St, Pittsfield MA, 01201     (413) 443-0188
– Admission is $20 for adults, $8 ages 13–17, and free for children 12 and under.


4. Nightwood

The Mount, American author Edith Wharton’s home, will be transformed into a magical winterscape. Collaboratively designed, this is a light and sound experience you will have to see and hear to believe! Nightwood “will immerse visitors in a series of vignettes designed to evoke elements of fantasy, mystery, and whimsy.” Tickets go on sale October 29, and must be purchased in advance. You will also be able to purchase concessions on site. Nightwood is an outdoor event, so you’ll want to wear your winter boots!

– 2 Plunkett Street, Lenox, MA 01240     413-551-5111
– Thursdays – Sundays from Nov. 20, 2020 to Jan. 3, 2021 (closed Nov. 26 & Dec. 24-25)
Purchase Nightwood Tickets


5. A Getaway to Devonfield Inn

When you plan your holiday escape to the Berkshires, make sure you book online with us so you can choose your favorite room or suite. Plan to experience wonderful Yankee hospitality. Enjoy these wonderful winter events, then return to your cozy room to anticipate your homemade, candle-lit breakfast fireside. When making your reservation, be sure to consider adding on a special enhancement, like a special guided hike through Lee, a horseback ride, or a massage. We will help make your season complete!


*Due to ever-evolving state and local restrictions, we recommend checking with any venue to make sure activities are still happening as planned.