Win a Trip to the Berkshires

Click to enter 2020-21 Win A Trip Contest!

Enjoy a two-night stay for two at The Red Lion Inn, an iconic landmark in the Berkshires whose warmth and character expresses timeless traditions. Located in Stockbridge, The Red Lion Inn offers not only the best of New England lodging, it boasts fine dining in the Main Dining Room, tavern fare at Widow Bingham’s Tavern and, in season, outdoor dining in The Courtyard. Dinner is included for one night. Make sure to say Hi to Norman, the feline lobby ambassador! Blackout dates include Columbus Day Weekend, 2021; December 24-31, 2021, and July 1-4, 2022. Reservations must be made for lodging and dining and subject to availability.

Two admission tickets to the Norman Rockwell Museum, a must see in the Berkshires. Be surprised and delighted at the magnificence of Rockwell’s large scale original paintings and discover the highly relatable world of American Illustration – the art that tells our stories, with ever-changing special exhibitions and engaging programs on a scenic 36-acre campus. Advance reservations are required with timed ticket entry.

Enjoy a Cidery tour and tastings for two at Hilltop Orchards, home of Furnace Brook Winery. Hike the trails in summer, take a stroll for apple picking in the fall or cross-country ski in the winter, all on this 100 year-old, family run orchard with breathtaking views. Advance reservations are required.



One lucky winner will be chosen on August 31!


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.

Explore the Many things to do in the Berkshires!