The Berkshires Blog

Music After Dark

By Darcie Sosa

One of the most popular things to do in the Berkshires is to attend a live musical performance. Most days of the week you’re able to find a great live performance somewhere in the region. There are many types to choose from and they continue to expand with more choices being added all the time. There is truly something for every taste including the upcoming Solid Sound, Wilco’s music and arts festival and Fresh Grass, a grassroots music festival at MASS MoCA.

If you start in the Northern part of the county, you’re situated perfectly to explore the exciting recent expansion at MASS MoCA, now the largest contemporary art museum in North America. After checking out the extraordinary exhibits during the day, you can enjoy refreshments at a pop-up bar and then take in a live show. This is a perfect way to enjoy a full day of culture and entertainment in the Berkshires.

MASS MoCA offers a variety of world, funk, indie-rock, punk, and hip-hop shows every month all year-round in their larger Hunter Center (be sure to check out their Solid Sound Festival: Wilco’s music and arts festival and Fresh Grass) as well as smaller performances in more intimate spaces. Past performances by Iron & Wine, Beck, My Morning Jacket, Steve Earle, Dinosaur Jr., and local band Whiskey Treaty Show are examples of what you can expect to find. Make sure you check their website for tickets to larger performances in advance.

Get grooving.

Location: Mission Bar & Tapas in Pittsfield.

Moving towards the center of the county, you will find Mission Bar + Tapas in downtown Pittsfield. Mission has frequent live music in an intimate setting. Sit at the bar or choose a cozy table to enjoy a glass of Spanish wine and tapas from the late night menu. The band performs from the front bay window under the glow of warm string lights. Whether it’s open mic night, a local or touring band, jazz or blues it’s going to be hard not to be moving in your seat and singing along. Some nights the audience can’t be contained and dancing breaks out. Mission can fill up so if you know you want to participate, get there early.

If you are interested in something more mellow, try the Gateways Inn, located in downtown Lenox. The Gateways offers live music starting at 7:30 Friday and Saturday nights and every night in July & August. Popular local artists fill the newly remodeled Garter Room lounge where a full bar menu is offered. The Gateways features an extensive wine list, an outstanding collection of single malt scotch and Italian grappa. No reservation is necessary but seating is first-come first-choice.

The Lion’s Den in Stockbridge is another great option for live music. The Lion’s Den has free live performances every night. A casual tavern located downstairs from the Red Lion Inn, this cozy and casual bar serves pub fare and cocktails. The Lion’s Den is the perfect choice for dessert and coffee, date night dinner, or just a fun spot to drop in and enjoy the music. Find out what’s on the calendar here, The Lion’s Den at The Red Lion Inn.

Many of our historic theaters present nationally known performers and bands, including the Mahaiwe Performing Arts Center in Great Barrington. Their 2017 summer schedule boasts Rusted Root on Monday, May 29th (Memorial Day), and The Beach Boys on August 15th. Berkshire Theatre Group offers up an eclectic mix of performers in The Garage at their Colonial Theatre location in Pittsfield.

Hoping to find something off the beaten track and not known to the masses? We have your pick. The Down County Social Club, also known as DCSC, is a speakeasy in Sheffield. Located in the basement of Race Brook Lodge’s Stage Coach Tavern, the DCSC features a selection of world, folk and rock groups. They have a full selection of wines and local brews served up in a funky atmosphere surrounded by mountains and the scenic Race Brook Falls is nearby.

Another hidden gem for live music is the Dream Away Lodge. The Dream Away is a legendary restaurant tucked deep in the woods of Becket, Mass. Over 90 years old, and originally thought to be a brothel and speakeasy, it became famous for hosting musicians, actors and society’s well to do. A visit in 1975 by Arlo Guthrie, Bob Dylan, and Joan Baez, solidified its’ place in local legend. The current proprietor has kept the tradition of live music most nights in the living room and has expanded the outdoor space to host larger bands. Community music night welcomes all to bring their acoustic instruments and share old-timey tunes in a decades-old tradition. The funky old house with a menu full of made-from-scratch, farm-to-table ingredients, makes this a musical place in the woods not to be missed.

Music and the Berkshires go hand in hand. You can depend on the large concert halls to continue to bring you world class entertainment but when you are looking for a more intimate or unique experience, you are now in the know. Try something new and discover more about what makes the Berkshires not only a beautiful destination but unique and entertaining as well.


Darcie Sosa is a Berkshire marketing/PR professional, who when isn’t working loves being outside hiking with her dogs, going to live music and theater shows, networking, trying new restaurants and volunteering for local nonprofits. She is an alum of Berkshire Community College, Massachusetts College of Liberal Arts, and the University of Massachusetts, Amherst.