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
Part of “Cool & Collected” at Kenise Barnes in Kent.D.H. Callahan
The Re Institute’s Holiday Show features more than 400 works by over 200 artists through Dec. 6, with a closing party from 1 to 4 p.m. that day.D.H. Callahan
Jennifer Terzian’s gallery showcases emerging and mid-career artists, with a focus on drawing, works on paper and painting.Provided
“From Ground to Gravity,” 2026, Oil on Canvas, 77 x 65 inchesProvided
“Nature Eternal,” 2026, Oil on Canvas, 77 x 47 inches.Provided
