Win a Trip to the Berkshires

Click to enter 2021 Win A Trip Contest!*

A 2020 contest winner will be chosen soon. Package details for 2021-22 contest to be announced

2020 Berkshire Trip Itinerary:

Wigwam Western Summit

2019-2020 Win a Trip getaway contributors

Enjoy 2-night accommodations for two at Wigwam Western Summit in North Adams, MA, in a beautifully restored cabin featuring modern comforts, air conditioning, and full baths. Wigwam also features a Sky Bar, Coffee House, Café & Bakery, and a gift shop loaded with local crafts, ice cream, honey and maple syrup. Come for a visit and enjoy a glass of wine, a draft beer, or a cup of coffee to go with the most amazing VIEW in the Berkshires!


Get your art on with two admission tickets to the Massachusetts Museum of Contemporary Art.  Open year-round and housed in a restored 19th century factory, MASS MoCA is the country’s largest center for contemporary visual and performing arts. The campus features free parking, affordably priced cafés, a full-service restaurant, delicious ice cream, great coffee, and an innovative microbrewery. (Pictured: Sol LeWitt, Wall Drawing #1152 part of Sol LeWitt: A Wall Drawing Retrospective at MASS MoCA, North Adams, MA. Photo by Kevin Kennefick.)

Tourists Welcome

Enjoy dinner for two in the Lodge at TOURISTS with a $100 Gift Card. Seasonal suppers along with George Howell coffees and sweet treats. Cocktails, house-infused spirits, beer, and wine.

We All Need Bodywork

Relax with an individual chair massages for two at WE ALL NEED BODYWORK, located in Adams, MA. WE ALL NEED BODYWORK is a Massage/Bodywork studio dedicated to help you in your process of healing and wellness.

Enter now!


Congratulations to our 2018-19 Win a Trip getaway winner, Kathy F. She will enjoy two nights at the Courtyard by Marriott in Lenox, general admission for two at Hancock Shaker Village, dinner for two at Methuselah Bar and Lounge, and a $25 gift certificate to Dory & Ginger. Sincere thanks to our Win a Trip getaway contributors.



One entry qualifies you for a chance to win the getaway. Winner selected by random drawing; winner will be excluded from future drawings for 12 months; packages do not include transportation; entrants must be 25 years of age or older; one entry per household; taxes and gratuities not included; no cash value; offers subject to availability; prize is not transferable; additional restrictions may apply to some packages; 1Berkshire employees and their families and its vendors are not eligible; void where prohibited by law. The prize package is valid for one year from date of winner’s receipt of the package unless otherwise noted. The package does not include airfare.

*You can only enter to win once.