Berkshires New Year's Eve 2020

Ring in 2021 in style with a Berkshires New Year’s Eve getaway at the Inn at Stockbridge. Book two nights or more and we’ll help you celebrate with a complimentary bottle of champagne and 6 delicious chocolate-covered strawberries!

The Berkshires make an excellent getaway no matter what the time of year. Museums, galleries, shows, festivals, dining, shopping, history, the great outdoors. You name it, the Berkshires have it. What better destination for seeing out the old year and ringing in the new?

Especially after a year like 2020!

This year’s NYE celebrations are bound to be a bit different. Masks, social distancing, and so many annual events that have gone virtual, or just plain gone. Still, nothing stops the calendar and there are still lots of fun things to see and do here in the Berkshires during the holiday season.

Most traditional New Year’s Eve parties and get-togethers had to be rethought this year but that doesn’t mean there’s nothing fun to do. Far from it! Below are just a few of the bigger holiday events and attractions in the Berkshires this New Year’s.

Berkshires New Year’s Eve Events

Winter Wonderland Walkway Dec 4 through 31
Enjoy a free stroll through the light bedecked Holiday Tree walkway at the Stockbridge Library. Masks and social distancing required.

free champagne New Year's Eve 2020

Festival of Trees: Legends of the Berkshires – Nov 28 through Jan 10, 2021
Festival of Trees is an annual holiday exhibition presented by the Berkshire Museum. This year’s event sees trees decorated around the “Legends of the Berkshires” theme. Trees are on display in the Berkshire Museum, shops, restaurants, offices, and other locations around Pittsfield.

Winterlights at Naumkeag – Nov 27 through Jan 2, 2021
Enter a wonderland of twinkling lights and fantastic landscaping with a visit to Naumkeag’s annual, outdoor Winterlights event. The fun and safe outdoor experience includes food, refreshments, and more. Tickets and more information.

NightWood at The Mount – Nov 19 through Jan 3, 2021
Visit Edith Wharton’s The Mount and see the property transformed into a fantastical winter landscape for the holidays: NightWood. The opening night gala on November 19 includes a pop-up bistro dinner, fire pits, seasonal cocktails, and a food truck. Learn more at

Bach at New Year’s – Dec 31, 6pm to 7:30pm
Eugene Drucker returns to lead a celebratory program for Bach at New Year’s in collaboration with the Mahaiwe Performing Arts Center, recorded on the Mahaiwe stage and streamed directly to you. Read more.

Lucinda Williams – It’s Only Rock and Roll: A Tribute to the Rolling Stones – Dec 31, 8pm to 9:30pm
Stream award-winning, singer/songwriter Lucinda Williams for a New Year’s Eve Tribute to the Rolling Stones. Visit for more information.

Inn At Stockbridge 2020 New Year’s Eve Package

free chocolate covered strawberries New Year's Eve 2020

Spend your Berkshires New Year’s Eve at The Inn at Stockbridge and we’ll help you celebrate with complimentary chocolate strawberries and champagne!

Best of all, the only requirement is a stay of 2 nights or more at our Berkshires inn over the New Year’s Eve holiday. There’s no special code to type in or request to make when booking to receive this free gift. You don’t even have to mention it, ever. Just book 2 nights or more over New Year’s and the champagne and chocolate-covered strawberries are automatically added to your room!

Our New Year’s Eve Package isn’t the only special offer we have for you, either. There is also a spa lodging package, a romance lodging package, a variety of of add-ons, and more. See them all on our Specials Offers and Packages page.

Happy Holidays!