PACK YOUR BAGS for a good time in the hub of the Berkshires. We scouted the city of Pittsfield and its surrounding areas, touching on some of the many places to eat, drink, stay and be entertained. There are many things to do and see for visitors of all ages.


HOTEL ON NORTH is the place for comfortable accommodations while experiencing the charm of the historic city of Pitts field. The hotel embraces the antiquity of the old Bess e-Clarke building; the menswear and sporting goods emporium was an exemplification of the industrial, active character of the city. The folks at Hotel on North went about the restoration to honor that history. Architectural features such as brick walls, tin ceilings, and obstructive columns are embraced and complimented through thoughtful design, while keeping a commitment to providing comfort for visitors. Each of the 45 rooms is unique in both floor plan and amenities. The collection of furnishings blend modern convenience and historic charm. The hotel opened its doors in 2015 and established itself as a go-to for the region, surviving the long stabilization period that independently owned hotels face. The hotel now serves as a sort of “living room” of the city, offering lodging, food, and entertainment.

Most weekend rates start under $200/night.
297 North St., Pittsfield


METHUSELAH BAR AND LOUNGE is a self-described “parallel universe where all the world’s problems are solved through belly laughs, love, edible and quaff able works of art.” This lounge features a small stage for live music, low couches and tables to help you relax while enjoying Cheesy Morsels or Piggy Parts. Perhaps more importantly, Methuselah boasts whiskeys from around the world on their menu. Enjoy one straight up, or perhaps a signature cocktail or one of 16 craft beers on tap.

391 North St., Pittsfield

If you prefer a shorter walk back to your room after dinner and drinks, EAT ON NORTH (owned and operated by the Hotel folks) features a larger space than most others along North Street, great for chatting at the bar or grabbing a more private table for your party. The American fare is prepared by executive chef Ron Red a, former supervisor of the White House kitchen during the Clinton Administration. Eat on North boasts the region’s first raw oyster bar, but also serves new variations of the ever-accessible chicken wings, cheeseburgers, and flat breads. They feature theatre menu selections to get you off to your show at Barring ton Stage Company on time.

297 North St., Pittsfield


Check the calendar for what band is playing on Saturday afternoon at BALDERDASH CELLARS. Balderdash is open for tastings each Saturday and Sunday from 1 – 5:00 p.m. Tastings are $8 per person and include seven wines. If you have a group of 12 or more, book a private tasting to hear even more about their offerings from the winemaker.

502 East St., Pittsfield
413.464.4629 (call for private tastings)

A night at the theatre is perfected by BARRINGTON STAGE COMPANY, bringing both new productions and re imagined classics to theatre-goers in the Berkshires. Their 2018 season will include the world premiere of The Royal Family of Broadway, loosely based on the Barrymore family, as well as the beloved West Side Story.

122 North St., Pittsfield

If you are in town during the week, catch a show at the COLONIAL THEATRE, specifically in their Comedy Garage on Thursday nights. With tickets going for just $5, you will enjoy sets from the next generation of great comedians. (That ticket also gets you a $5 drink at Methuselah)

111 South St., Pittsfield

THE BERKSHIRE MUSEUM is currently featuring an exhibition entitled Morgan Bulkeley: Nature Culture Clash. The paintings and sculptures by Bulkeley, a Berkshire native, are curated by Geoffrey Young, of the Geoffrey Young Gallery in Great Barrington, and will be on display through Feb. 4.

39 South St. (Route 7)

If you prefer the great outdoors, Pittsfield offers a short drive to dozens of hiking, biking, and skiing destinations. PLEASANT VALLEY WILDLIFE SANCTUARY in nearby Lenox is a great option for hikers of any experience, including an accessible All Persons Trail. The sanctuary also boasts an active beaver colony, so keep an eye out for dams. PITTSFIELD STATE FOREST offers 1,100 acres and 30 miles of trails whether you prefer to hike, mountain bike, or go horseback riding.

Pleasant Valley Wildlife Sanctuary
472 West Mountain Road, Lenox

Pittsfield State Forest
1041 Cascade St., Pittsfield


Before you leave, pick up some locally produced goods for your friends and family:

The folks at Shire City Herbals took a German grandmother’s recipe and turned it into FIRE CIDER. Made with all raw, organic, health-promoting ingredients, the result is “potent and energizing.” Fire Cider can be served simply as a tonic, mixed into a cocktail for extra kick, or baked into your next desert. Available at several Pittsfield locations including Dottie’s Coffee Lounge and Methuselah Bar and Lounge.
Shop online at

Annie Selke has been producing fun and beautiful home textiles since she started PINE CONE HILL in 1994. Your access to the nationally-recognized, locally-based company is their outlet. Add Pine Cone Hill bedding, curtains, or table linens to your collection — perhaps something in Greylock Navy?

125 Pecks Rd, Pittsfield

If you didn’t already stop by BALDERDASH CELLARS, you can pick up their latest vintages at several shops around Pittsfield.

502 East St., Pittsfield