Six Fabulous Berkshires Holiday Traditions

Wreath of evergreens decoratoed with colorful holiday ornatments and pine cones.Creating a portfolio of fabulous holiday traditions is easy to do in the Berkshires. Home to a bevy of artists and artisans, musicians and performers, the small towns and villages in western Massachusetts break out the best and brightest for the holiday season. Fill your calendar with music, theater, nostalgia and more by visiting the Berkshires. The innkeepers at Staveleigh House Bed and Breakfast invite you to sample true Berkshire hospitality this season with a line-up of magical holiday events.

Stockbridge Main Street at Christmas: December 6, 7, & 8
Inspired by Norman Rockwell’s painting Stockbridge Main Street at Christmas, this weekend of festive events aspires to re-create the feeling of a quintessential small New England village during a simpler time. Highlights of the celebration include a popular house tour of some of the area’s historic homes, a caroling and luminaria walk, a holiday concert, and the Sunday spectacular event where the Main Street of Stockbridge magically transforms into the vision captured by Rockwell’s painting, complete with vintage cars.

Mistletoe and Martini Cabaret Train: Saturday, November 30 and December 14
Imagine riding the rails while being serenaded with popular holiday tunes. It’s a “you bring the martinis and we’ll bring the mistletoe” event hosted by the Berkshire Scenic Railway Museum in Lenox, MA. This often sold-out event is a spirited way to get into the holiday groove. Have kids? Book the Tinseliner Trains with Santa and tag your tree at PopCares tree lot for pick up later.

Handels’ Messiah Sing Along: Saturday, November 30 at 4:00 PM
Always planned for Thanksgiving weekend, this annual traditional singalong signals the start of the holiday season. Lead by professional choral director, Frank Nemhauser and accompanied by the Berkshire Bach Players, everyone is invited to join in the chorus and sing the Hallelujahs. No musical talent? Just sit and listen to the glorious music composed by Handel in 1741.

Handmade Holiday Festival: December 7 & 8
Looking for some one-stop holiday shopping? Head out the the annual Handmade Holiday Festival at The Stationary Factory in Dalton, MA. You’ll find all manner of hand crafted items for sale: jewelry, pottery, food items and more, showcased by local and regional artisans, farmers, and food producers. Show your support for local entrepreneurs and shop local this holiday season.

A Christmas Carol: Dates and Times vary, December 7 through 21
Can the holiday season truly be complete without seeing a performance of Dicken’s classic A Christmas Carol? On stage at the Colonial Theater in Pittsfield, MA, the Berkshire Theater Group presents this traditional tale of the miser, Scrooge, and his redemption by visits from four spirits.

Holiday Shindy: December 14th and 15th, 10 AM to 5 PM
Held at the former Shire City Sanctuary (now the Al-Khalil Cultrual Center), the 13th annual Holiday Shindy is perhaps one of the most amazing holiday fairs in the Berkshires. Featuring artisans working in varying mediums from jewelry to wood , you’ll find unique and beautiful items to delight everyone on your shopping list.

Book your holiday getaway today and make your way to the southern gateway to the Berkshires at the Staveleigh House Bed and Breakfast in Sheffield, MA.

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