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Date Night Adventures in Pittsfield

Date Night Adventures in Pittsfield
Camille Reddick
Camille Reddick
September 27, 2024

It's date night in the Berkshires! With its beautiful views and moody atmosphere, it's no surprise that Pittsfield is one of the best spots for a date night. Couples can enjoy everything from dinner and drinks to a live show and museum tour. Get ready to fall in love in the mountains with these five date night activities in Pittsfield, MA.

Catch a Show at Barrington Stage Company

Show at Barrington Stage Company

Don't miss a chance to see a live show at the iconic Barrington Stage Company. Since its founding in 1995, Barrington Stage has put on a number of award-winning productions. It is also the recipient of several Elliot Norton/Boston Theatre Critics Awards, Berkshire Theatre Awards, Berkies, and Outer Critics Circle Awards. This date-night idea takes some planning because you'll need to book tickets ahead of time.

Go Bowling at K&M Bowling, Arcade, and Bar

Do you hate sitting still on a date? This fun bowling alley, arcade, and bar is open seven days a week. Cosmic bowling happens on Fridays and Saturdays.

Visit the Berkshire Museum

The Berkshire Museum is the perfect pick for a couple looking for an enriching date idea. Visitors can enjoy a newly renovated second-floor housing more than 40,000 treasured objects spanning multiple exhibits. Of course, the famous first floor of the museum is dedicated to the 3,000-square-foot Feigenbaum Hall of Innovation. You'll have plenty to talk about on your date as you move from room to room to discover exhibits covering mummies, reptiles, ecosystems, artifacts, and local artists right here in the Berkshires! With the museum being open until 5 p.m. every night of the week, this is something you'll need to plan as a before-dinner activity.

Get Some Drinks at Methuselah Bar and Lounge

This cozy bar and lounge is the perfect spot for enjoying conversation over some drinks. Choose from 16 craft beers on draft and a selection of flavor-infused cocktails. Methuselah also has some great "little bites" that are perfect for sharing. The pulled pork tacos, cheese bites, pigs in a blanket, and mushroom tarts hit the spot. Of course, you can also plan for drinks and dessert after dinner to enjoy homemade lemon chèvre cheesecake made with local goat cheese, lemon curd, and blueberry compote.

Enjoy a Nice Dinner at Mazzeo Ristorante

Mazzeo Ristorante

Mazzeo is widely considered the best spot for a dinner date in Pittsfield. The menu at this family restaurant boasts authentic Italian cuisine made with fresh ingredients. Dine on homemade pasta, succulent veal, chicken parmesan, and fresh seafood with sauce that's to die for! There's no better place in the Berkshires for authentic risotto or perfectly crispy calamari. The portions are also generous! The dessert menu at Mazzeo Ristorante boasts house-made tiramisu that always tastes better when shared with two forks.

Planning Your Date Night in the Berkshires

There's clearly no shortage of magical date night activities in Pittsfield, MA! Of course, not every date takes place after dark. If you have a busy day of sightseeing planned, plan for a romantic meal before noon at one of the best places for brunch in Pittsfield, MA.