Where to find music in The Berkshires

Thanksgiving’s over, the leftovers are gone, and now it’s time to get out of the house and see some live entertainment. 

Luckily, there are many options to choose from in the region. Winsted has gradually seen its options for live music expand. Located at 524 Main St., 2nd Home Lounge serves tapas, wine and beer on draft in a cozy setting that lives up to its name. Grab an armchair or a sofa and share a charcuterie board with beers from Little Red Brewing, Norbrook, and Great Falls, as well as locally produced wines and spirits while you watch local musicians or comedians perform. 2nd Home Lounge is unique in that it emphasizes local. Hours vary so check the website for specifics: 2ndhomelounge.com

The Gilson Theater at 345 Main St. has live jazz every Sunday from 5 to 7 p.m. Seating is limited and tickets are typically $15 and are available at the door or online at gilsoncafecinema.com

Further on up the road, Little Red Barn Brewers (LRB) features a wide range of handcrafted brews in a former factory. With ample seating inside and out, it’s a popular spot, with live acoustic music and trivia nights throughout the week. Partnering with the Old Riverton Inn, LRB has recently expanded into a massive adjacent space where it will have live events. For more info, check the website: lrbbrewers.com

Continuing north, Norbrook Farm Brewery in Colebrook serves some of the best beer around in a bucolic setting with great views overlooking hop vines, grazing sheep and stunning sunsets. Surrounded by 450 acres of wooded land, it also boasts trails popular with mountain bikers, hikers and Frisbee golfers. In warmer weather, the parking lot is usually packed with food trucks, and Thursdays nights in August are cruise nights with vintage cars on display. Inside, there’s ample seating; outside, fire pits allow year-round libation. Norbrook has a regular schedule of live acoustic music, typically on weekends. For a complete schedule, see www.norbrookfarm.com

Undoubtedly, one of the finest live event spaces in northwestern Connecticut, Infinity Music Hall in Norfolk has top-notch booking with an approximately 300-person capacity. Built in 1883, it’s a gorgeous venue with wainscoted walls, colorful stained glass windows and a state-of-the-art sound system. Run by Good Works Entertainment, Infinity Music Hall has resumed a full booking schedule. Downstairs the bistro serves small plates and drinks in a convivial atmosphere. Check the website for popular national touring acts: www.infinityhall.com

With recent efforts to beautify and revitalize, Canaan is looking better than ever. The Music Lab’s mission is “To Teach, Inspire and Promote Music in the Community.” Located at 93B Main St., The Music Lab serves as a practice space and a recording studio, and hosts an acoustic night hosted by Mark Yard every Thursday from 6:30 to 9:30 p.m.: www.musiclabct.com

The Colonial Theatre just up Route 7 occasionally offers live music, usually in the form of sponsored benefit concerts and, lately, free movies in a gorgeous, mid-century movie theater. Performances have been held downstairs in the main space, but there’s also a stunning upper level: www.canaancolonial.com

Crossing the state line into Massachusetts, Dewey Hall on Route 7 in Sheffield is a beautiful events space featuring folk music, contra dancing, open mics and community events. The focus is on the traditional. See the calendar at www.deweyhall.org

Just off of Route 23, The Egremont Barn in Egremont is one of the coolest venues around. As the name implies, the action happens inside a beautiful barn built in 1786. Comedian Jenny Rubin and musician Nick Keene curate a hip booking schedule open from Wednesday to Sunday from 5 p.m. onward. It features food and drink, and has become one of the most desired places to play in the Berkshires. There’s also accommodation at the adjacent inn. See the site: www.theegremontbarn.com

Tucked way back on Undermountain Road, Race Brook Lodge in Sheffield offers eclectic musical and cultural programming, often with a global flavor. Live performances typically happen in the large barn situated on stunning property that also features an inn and a restaurant. Check the website for complete listings: rblodge.com/events

The Mahaiwe Performing Arts Center in Great Barrington is one of the more stunning venues in the area, with a capacity of 681 that makes it ideal for larger live events. High-brow programming includes movies, plays, comedy, and music that ranges from classical to rock ‘n’ roll. For a full list of programming, see mahaiwe.org

For those seeking something really different, Familiar Trees bookstore at 80 Railroad St. in Great Barrington programs music from time to time in its adjacent gallery. Recent shows have included electronica soundscapes and avant garde jazz. Check the site for listings: www.familiartrees.com

Big Elm Brewery at 389 Stockbridge Road in Great Barrington has live acoustic music in a lively setting where great beer and spirited conversation flow: www.bigelmbeer.com

Latest News

Legal Notices - November 6, 2025

Legal Notice

The Planning & Zoning Commission of the Town of Salisbury will hold a Public Hearing on Special Permit Application #2025-0303 by owner Camp Sloane YMCA Inc to construct a detached apartment on a single family residential lot at 162 Indian Mountain Road, Lakeville, Map 06, Lot 01 per Section 208 of the Salisbury Zoning Regulations. The hearing will be held on Monday, November 17, 2025 at 5:45 PM. There is no physical location for this meeting. This meeting will be held virtually via Zoom where interested persons can listen to & speak on the matter. The application, agenda and meeting instructions will be listed at www.salisburyct.us/agendas/. The application materials will be listed at www.salisburyct.us/planning-zoning-meeting-documents/. Written comments may be submitted to the Land Use Office, Salisbury Town Hall, 27 Main Street, P.O. Box 548, Salisbury, CT or via email to landuse@salisburyct.us. Paper copies of the agenda, meeting instructions, and application materials may be reviewed Monday through Thursday between the hours of 8:00 AM and 3:30 PM at the Land Use Office, Salisbury Town Hall, 27 Main Street, Salisbury CT.

Keep ReadingShow less
Classifieds - November 6, 2025

Help Wanted

Weatogue Stables has an opening: for a full time team member. Experienced and reliable please! Must be available weekends. Housing a possibility for the right candidate. Contact Bobbi at 860-307-8531.

Services Offered

Deluxe Professional Housecleaning: Experience the peace of a flawlessly maintained home. For premium, detail-oriented cleaning, call Dilma Kaufman at 860-491-4622. Excellent references. Discreet, meticulous, trustworthy, and reliable. 20 years of experience cleaning high-end homes.

Keep ReadingShow less
Indigo girls: a collaboration in process and pigment
Artist Christy Gast
Photo by Natalie Baxter

In Amenia this fall, three artists came together to experiment with an ancient process — extracting blue pigment from freshly harvested Japanese indigo. What began as a simple offer from a Massachusetts farmer to share her surplus crop became a collaborative exploration of chemistry, ecology and the art of making by hand.

“Collaboration is part of our DNA as people who work with textiles,” said Amenia-based artist Christy Gast as she welcomed me into her vast studio. “The whole history of every part of textile production has to do with cooperation and collaboration,” she continued.

Keep ReadingShow less