Date Night Dinner Spots: Pittsfield

Check out our favorite date night spots in downtown Pittsfield that offer our favorite apps, entertainment a little romance and of course, fun!

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  • 1
    Patricks Pub.jpg

    26 Bank Row, Pittsfield, Massachusetts 01201
    413-499-1994

    Wings, beer and the comfort of home

    Patrick's Pub is the casual spot to go if you and your other half want a relaxing, comfortable atmosphere. With 16 different draft beers and insatiable wings, Patrick's comfort food is second to none. Whether you start your night here or want to enjoy a nightcap, drop in and check out the warm, wood-toned space.

    Insider Tip: If you hate trying to find a parking spot as much as the next person, avoid the dinner rush, otherwise you'll be circling around for a bit. If you don't mind a little walk, try and snag a spot around the corner, near the Berkshire Museum. 

  • 2
    District Kitchen and Bar.jpg

    Marc J. Wrzesinski

    40 West Street, Pittsfield, Massachusetts 01201
    413-442-0303

    Everything you could want in an intimate atmosphere

    District is well known for its small, yet personal atmosphere. This is a great spot to take your date if you want the intimate feel, but not the complete romantic setting. From local beers to sparkling wines, this cozy bar offers more than meets the eye. Their food is exquisite and is sure to please your taste buds, offering American cuisine with gastropub influences.

    Insider Tip: You MUST try the house fries with garlic aioli. The perfect french fry with a twist.

  • 3
    Rainbow Restaurant.jpg

    109 First Street, Pittsfield, Massachusetts 01201
    413-443-0002

    Newly renovated, with much more to offer than delicious meals

    The Rainbow has called Pittsfield home since the early 1900's, and is a well known establishment where couples have gone to on a night out for years. Now with a more open space and a collection of craft beers, The Rainbow is a go to if atmosphere is what's most important. Their menu offers an array of divine food and any drink you desire, will be made perfect each time. You can't go wrong taking your date here!

    Insider Tip: If you're going to Shakespeare in the park, but want the Rainbow for dinner, they will deliver it to you across the street!

  • 4
    Mission Bar and Tapas

    438 North Street, Pittsfield, Massachusetts 01201
    413-499-1736

    Rustic setting with live music

    If you're in the mood to listen to live music while you enjoy your date, stop by Mission. They offer some delicious meals, with accommodating drinks in a laid back atmosphere. Since they're open until Midnight, Monday-Saturday, you and your date can come early or stay late, all while appreciating the unique music and atmosphere that Mission offers.

    Insider Tip: If you're there to talk more than listen to the music, sit in the back near the bar, that way you can hear your date better.

  • 5
    Elizabeth_s restaurant.jpg

    1264 East Street, Pittsfield, Massachusetts 01201
    413-448-8244

    Low-key Italian spot with delicious food

    Elizabeth's is the best place to take your date if you really want to get to know them. With limited seating, and a cozy atmosphere, this restaurant offers authentic divine Italian dishes. The owners are very personable and care about making your experience a positive one. If you want to spend an evening dining in a one of a kind place that offers amazing home-cooked dinners, be sure to put Elizabeth's at the top of your list! 

    Insider Tip: Make a reservation, as they fill up quickly!

  • 6
    Methuselah bar and Lounge

    391 North Street, Pittsfield, Massachusetts 01201
    413-344-4991

    Organic wine & craft beer in the busy downtown area

    Methuselah is well known for their array of craft beer and cocktails. If date night takes you here, be sure to branch out and try something different. In a low lighted, rustic setting, Methuselah is a quiet yet upbeat spot right in downtown Pittsfield. 

    Insider Tip: If you want to miss the party crowd, be sure to eat before 9:30PM

  • 7
    Roasted Garlic.jpg

    483 West Housatonic Street, Pittsfield, Massachusetts 01201
    (413) 499-9910

    Wood fired pizza, signature apps, & fresh ingredients

    If fun and lively is the type of spot you want to go on date night, look no further! The Roasted Garlic's upbeat atmosphere and signature appetizers make it a go to spot here in Pittsfield. High top tables and great drinks make for the perfect casual date night! If you haven't been, definitely give it a try and see what everyone's talking about.

    Insider Tip: If there's a sports game on, they tend to be busier than usual as they have 6 large TV's broadcasting.