NO NEED TO REINVENT THE WHEEL when it comes to what to do and see this holiday season. We’ ve pulled together tried-and-true Berkshire traditions, plus a few events on their way to the coveted designation. From local marketplaces and old-fashioned holiday strolls to timehonored performances and historic venues at their most festive, these traditions have kept up with the times— with elaborate decorations, sustainable gifts, sophisticated food, and intricate textile arts.
Local Makers
Strolls & Light Shows
NO NEED TO REINVENT THE WHEEL when it comes to what to do and see this holiday season. We’ ve pulled together tried-and-true Berkshire traditions, plus a few events on their way to the coveted designation. From local marketplaces and old-fashioned holiday strolls to timehonored performances and historic venues at their most festive, these traditions have kept up with the times— with elaborate decorations, sustainable gifts, sophisticated food, and intricate textile arts.
Local Makers
If you consider shopping for the holidays a chore, these Berkshire markets will change your mind. Like farm-totable restaurants, workshop-to-table markets offer unique local items by local makers.( There is no entry fee to the events unless noted.)
First up is Festive Holiday Market at Greylock WORKS in North Adams on Nov. 22 from 10 a. m. to 4 p. m. Local farmers, designers and artisans showcase their fresh food and crafted goods in the 30,000-square-foot open market at 508 State Rd.
Visit Berkshire Grown’ s Winter Market from 10 a. m. to 1 p. m. at Greylock WORKS on Nov. 23 and Dec. 21 and at the Housey Dome in Housatonic on Nov. 22, Dec. 20, Jan. 17, and Feb. 21. Connect with community farms and farmers selling winter vegetables, meats, dairy, eggs, syrup, and baked goods.
Holiday Marketplace & Gallery of Wreaths at Berkshire Botanical Garden, 5 W. Stockbridge Rd., Stockbridge, returns Dec. 5 – 7. The legendary preview party( early wreath-buying, music, and hors d’ oeuvres) is Dec. 5 at 5 p. m. The Holiday Marketplace runs Dec. 6 – 7, 10 a. m. to 4 p. m., featuring 100 unique, one-of-a-kind designer wreaths, holiday-blooming amaryllis and paperwhites, succulent arrangements, garlands, hanging terrariums, and gifts by regional artisans. Tickets to the preview party can be purchased at berkshirebotanical. org.
First Congregational Church’ s Holly Fair in Stockbridge, presented by the Women’ s Service League with all proceeds going to charity, is a hometown fair with handmade crafts, gifts and decorations, holiday greens, baked goods, Tea Room, Grandma’ s Attic,
Santa Claus, and a silent auction crossstitch. It’ s on Dec. 6, 10 a. m. to 1 p. m., at 4 Main St.
The Holiday Shindy, now in its 18th year, is the Berkshire benchmark of spectacular sustainable tradition. It’ s your chance to shop directly from local farms and makers, from soaps and tinctures to cookies and calendars. It will be held on Dec. 13, 10 a. m. to 4 p. m., at the Masonic Temple, 116 South St., Pittsfield. $ 3 admission; children under 12 free.
GBAM( Great Barrington Art Market) Delightful & Delectable Holiday Market will be held this year on the second floor of the Great Barrington Food Co-Op, 34 Bridge St. It will feature 25 makers of local and regional handmade gifts and giftable treats, all thoughtfully curated. Mark your calendar for this market on Dec. 20, 10 a. m. to 5 p. m.
Pittsfield’ s Berkshire Winter Bazaar hosted by Thistle‘ n Thorn Floral is an extraordinary collection of handmade goods and handcrafted art from the Berkshires and beyond. The bazaar is on Dec. 6, 11 a. m. to 4 p. m. at the Holiday Inn & Suites, 1 West St., Pittsfield.
Berkshire Art Center’ s Faculty Show & Holiday Sale celebrates art, community, and the season of giving. The opening reception and cocktail party is Dec. 5, 5 to 7 p. m., and the Holiday Sale is Dec. 6, 10 a. m. to 5 p. m., 13 Willard Hill Rd., Stockbridge. Details can be found at berkshireartcenter. org.
Strolls & Light Shows
From Berkshire Main Streets dressed up for the holidays to historic properties that sparkle and shine with thousands of lights, outdoor holiday activities in the
Berkshires are the bomb! Bundle up and take in the magic of our small towns and beauty of our outdoor spaces.
Edith Wharton’ s The Mount brings back the winter sound and light show, NightWood for its sixth season, where visitors step into a fantastical landscape of music, light, and nature under the stars. This year includes two new encounters, a revised path, and enhanced lighting and sound. The illuminated three-quarter-mile route winds through the woods and gardens of The Mount in Lenox, with warming stations and seasonal drinks. NightWood is open from 5 to 8 p. m. on Nov. 21, 22, 26, 28, 29; Dec. 6, 12, 13, 18 – 23, 26 – 31; and Jan. 2 and 3. Purchase tickets at edithwharton. org.
LumiNAMA Lights in North Adams kicks off the season with the city’ s tree-lighting ceremony on Nov. 26 at 5 p. m. at Monument Square on Main Street, which includes a visit from Santa with free goodie bags for the children. Downtown businesses on Main, Holden, Center, and Eagle streets also flip the switch that weekend to show off their creative window light displays. Additional light displays at Pocket Park add to the sparkle of a holiday downtown to remember, until Jan. 2. Find updates at luminama. com.
Historic Naumkeag estate in Stockbridge, presents the eighth season of Winterlights, Wednesdays through Sundays, Nov. 28 – Jan. 3, 4:30 to 9 p. m.( closed Dec. 24 – 25). Thousands of shimmering, artfully designed holiday light displays along a three-quarter mile path guide the whole family through a world of magic and enchantment while listening to festive music and enjoying seasonal treats. Tickets can be purchased at thetrustees. org / program / winterlights-massachusetts.
NightWood ' s illuminated three-quarter-mile route winds through the woods and gardens of The Mount in Lenox.( Courtesy of The Mount)
Holiday 2025 2023 BERKSHIRE MAGAZINE // 11