2025 Holiday Events in Great Barrington & the Southern Berkshires

winter lights sign at

Holiday Events in Great Barrington & the Southern Berkshires (2025 Guide) 

Winter in the southern Berkshires is full of small-town charm, festive lights, and timeless New England traditions. If you're staying at East Rock Inn, you’ll be minutes from some of the region’s most beloved holiday happenings. We've put together some of our favorite 2025 holiday events in Great Barrington, Stockbridge, and Lenox. 


⭐ Great Barrington Holiday Shop, Sip & Stroll 


December 13, 2025 — 3:00–8:00 PM 


Downtown Great Barrington 


This annual community celebration fills Main Street with festive lights, music, art installations, family activities, warm drinks, and extended shopping hours. A perfect way to enjoy the holiday spirit, just minutes from East Rock Inn. 


Event page:  https://www.facebook.com/events/747667967663433 



⭐ Charlie’s Trains! at Saint James Place (Great Barrington) 


December 13–14, 2025 


Saint James Place 


A free, family-friendly holiday tradition featuring elaborate model-train displays inside the historic Saint James Place. Perfect for kids, collectors, and anyone who loves festive holiday villages. 


Event listing: https://saintjamesplace.net/events/ 



⭐ Stockbridge Main Street at Christmas 


December 6–7, 2025 


Stockbridge, MA 


An iconic New England holiday celebration inspired by Norman Rockwell’s famous painting. Includes historic home tours, wagon rides, caroling, concerts, and the famous full Main Street reenactment. 


Official info: https://stockbridgechamber.org/visit/stockbridge-main-street-at-christmas/ 



⭐ Winterlights at Naumkeag (Stockbridge) 


November 28, 2025 – January 3, 2026 (Wednesdays–Sundays) 


Naumkeag, Stockbridge 


A magical light show that transforms the Naumkeag gardens into glowing winter pathways and artful light displays. Ideal for families, couples, and visitors looking for a festive Berkshire tradition. 


Tickets & details: https://thetrustees.org/program/winterlights-massachusetts/ 


 

⭐ Holiday Marketplace at Berkshire Botanical Garden 


December 5–7, 2025 


Housatonic, MA 


A charming artisan market offering handcrafted gifts, winter plants, wreaths, and seasonal décor. A great place to find locally made holiday gifts just minutes from Great Barrington. 


Event details: https://www.berkshirebotanical.org/events/2025-holiday-marketplace 


✨ Celebrate the Holidays at East Rock Inn 


With cozy rooms, easy parking, and a central location close to Great Barrington, Stockbridge, and Lenox, East Rock Inn is the perfect home base for enjoying these festive winter events. Whether you're here for holiday shopping, seasonal lights, or small-town celebrations, book now and enjoy all the Berkshires offers for a warm and memorable holiday getaway. 


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The Berkshires offer a delightful sip for every palate, from award-winning breweries to cozy wineries and innovative distilleries. We’ve compiled a few of our favorites. Great Barrington: A Craft Beer Lover's Paradise Barrington Brewery & Restaurant in Great Barrington is a local favorite renowned for its commitment to sustainability. Its solar-powered brewing process produces a lineup of award-winning beers, perfectly paired with its delicious pub fare. Craving a relaxed vibe? Head to Big Elm Brewing , also in Great Barrington. This brewery boasts a constantly rotating selection of local favorites, offering a chance to discover the unique styles and flavors crafted by the region's independent brewers. Craft Beers Beyond Great Barrington For a wider exploration, venture out to Bright Ideas Brewing in North Adams. This innovative brewery pushes boundaries with its experimental brews. If ciders are your thing, don't miss Berkshire Cider Project , also in North Adams, offering handcrafted ciders made with locally-sourced apples. The Berkshires craft beer scene continues to evolve with the recent arrival of Hot Plate Brewing Co. in downtown Pittsfield. This Latina-owned brewery offers a unique perspective on the craft beer world, with a focus on innovative recipes and a welcoming taproom experience. Local Berkshires Wineries and Vineyards Les Trois Emme Vineyard and Winery is less than five miles from East Rock Inn and hosts weekend wine tastings in its comfortable tasting room. This locally owned vineyard is minutes from Great Barrington, and you can try a range of whites and reds. For an experience that marries wine tasting with breathtaking scenery, venture out to Four Winds Vineyard in nearby Canaan, Connecticut (just a 23-minute drive). Specializing in estate-grown Bordeaux varietals, they offer tastings and tours, allowing you to discover the unique terroir and meticulous craftsmanship behind each sip. For those seeking off-the-beaten-path tastings, explore hidden gems like Balderdash Cellars in Richmond. This boutique winery produces ultra-premium wines from world-class California vineyards, offering a unique experience for discerning palates. Local Berkshires Spirits and Cocktails The Berkshires aren't just about beer and wine. If you're looking for a unique spirit experience, look no further than Berkshire Mountain Distillery in Great Barrington. Their small-batch gins and vodkas, crafted with locally sourced ingredients, are a testament to the region's commitment to quality and innovation. Sample their award-winning spirits neat or ask the bartenders to create a signature cocktail for you. Want to learn more about the craft beverages we’ve suggested? Here are helpful links to get you started: Barrington Brewery & Restaurant: https://www.barringtonbrewery.net/ Big Elm Brewing: https://www.bigelmbeer.com/ Bright Ideas Brewing: http://brightideasbrewing.com/ Berkshire Cider Project: http://www.berkshire-cider.com/ Hot Plate Brewing Co.: https://www.hotplatebeer.com/ Four Winds Vineyard: https://crowleywines.com/vineyard/ Balderdash Cellars: https://www.balderdashcellars.com/ Berkshire Mountain Distillery: https://berkshiremountaindistillers.com/our-products/ Les Trois Emme Vineyard: https://www.ltewinery.com/ Be sure to drink responsibly and plan to have a designated driver or take a rideshare/taxi to and from your destinations. You’re just a short drive away to any of these experiences from East Rock Inn. Book Now and make East Rock Inn your home base in the Berkshires.
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