Enjoy a Berkshire Season Filled with Festive Holiday Events

Thanksgiving is just a week away and that means it’s time to get in the holiday spirit! We’re here to help with a lineup of merry events and activities, from an old-fashioned candlelit evening to a thoroughly modern ski with Santa. So grab your calendar and plan a stay at Staveleigh House, where you’ll be close to all these area activities—and nestled down in cozy comfort when the day is done.A picture frame made of holly with these words inside of it: Festive Holiday Events in the Berkshire Mountains.

Festival of Holidays. The Old Stone Store here in Sheffield becomes a winter wonderland of wonderful gifts during this annual fundraiser for the Sheffield Historical Society. Not only can you find unique gifts, you’ll be gifting the museum too!
Old Stone Store
137 Main Street, Sheffield, MA
Information: 413-229-2694

Annual Holiday Marketplace. A highlight of this yearly event at the Berkshire Botanical Garden is always the stunning Gallery of Wreaths, a 28-year tradition that offers one-of-a-kind wreaths. Also available for purchase are traditional centerpieces and swags, flowering plants and hand made gifts by regional craft vendors.
December 1-2, 2018
Saturday, 11:00 a.m. – 5:00 p.m.
Sunday, 10:00 a.m. – 4:00 p.m.
Berkshire Botanical Garden
5 West Stockbridge Road, Stockbridge, MA

Stockbridge Main Street at Christmas. Bring the entire family for a magical weekend, imagined as painter Normal Rockwell envisioned it. The festivities include home tours, caroling by candlelight, antique cars and a real-life re-enactment of Rockwell’s New England village.
November 30, December 1-2, 2018
Main Street, Stockbridge, MA

Candlelit Evening. Tradition reigns at Hancock Shaker Village where the old-time setting is awash in twinkling lights. Stroll by lantern light to visit the animals and hear music in the historic 1910 Barn. Then settle in at the Brick Dwelling for a holiday reading, snacks and drinks. Finish the evening caroling by luminaria through the historic village. Next day, enjoy a Holiday Tea including savory and sweet treats, such as Shaker Tea Cakes, a specialty of the house.
Candlelit Evening
December 1 and 8, 2018
3:00 p.m. – 7:00 p.m.
$45/adults, $25/children
Holiday Tea,
December 2 and 9, 2019
12:00 p.m. – 4:00 p.m.
Hancock Shaker Village
1843 West Housatonic Street, Pittsfield, MA

Holiday Shop, Sip & Stroll. Great Barrington gets extra festive on December 8 with a central bonfire, holiday music, a food court, fireworks and more fun activities. It’s a great time to do a little Christmas shopping too!
December 8, 2018
3:00 p.m.
Downtown Great Barrington, MA
Information: 413-528-9697

It’s a Wonderful Life. It just isn’t Christmas without a viewing of this beloved classic. Catch the free screening on December 21 at Mahaiwe Performing Arts Center and see Clarence get his wings!
December 21, 2018
7:00 p.m. (first come, first serve)
Mahaiwe Performing Arts Center
14 Castle Street, Great Barrington, MA

Ski with Santa. The jolly old elf himself will be taking to the slopes on Christmas Eve at Ski Butternut and you can join him. Wear your merriest outfit , enjoy skiing and boarding, and get a complimentary Facebook photo with Santa.
December 24, 2018
11:00 a.m. – 2:00 p.m.
Ski Butternut
380 State Road, Great Barrington, MA

Ready for some R&R after all that activity? Head back to Staveleigh House Bed and Breakfast for a quiet night by the fire. Call today for a reservation or book online!