Dinner and a Show in Pittsfield, MA

Pittsfield’s downtown, known as the Upstreet Cultural District, boasts a lively roster of music, dance, theatre, community festivals, and celebrations, including two highly acclaimed professional theatres – the Colonial Theatre, part of Berkshire Theatre Group, and Barrington Stage Company.

Make it a full evening with dinner beforehand at one of our local restaurants. Whether you are looking for fine dining or something more casual, our downtown has got you covered.

 

Patrick’s Pub and 101 Restaurant & Bar

Patrick’s Pub is a great casual option. This family-owned restaurant offers a variety of menu items from soups, salads & sandwiches to burgers and entrees. If appetizers are your thing, you will want to order Patrick’s famous buffalo wings and their nachos which were voted Best in the Berkshires. Patrick’s sister restaurant, 101 Restaurant & Bar, on the second floor of The Holiday Inn, features an original, southern-inspired menu, that is sure to delight.

 

RARE 297 Steakhouse and RJ’s Restaurant

For a top-of-the-line experience, RARE 297 Steakhouse provides tender steaks, savory seafood, and pasta dishes in an elegant atmosphere. RARE is known for their signature dish, the Filet Mignon Oscar. Their sister restaurant, RJ’s Restaurant, offers seafood, chops, and pasta, and The Berkshire Eagle’s Best of the Berkshires award-winning “Best Steak”.

 

Espetinho Carioca, Tito’s Mexican Bar & Grill, and BB’s Hot Spot at The Lantern

If international cuisine tickles your taste buds, choose from Brazilian, Mexican, or the mouthwatering flavors of the Caribbean.

Espetinho Carioca brings the best of Brazilian cuisine to the Berkshires, focusing on authentic dishes like feijoada and churrasco to share the Brazilian culture through the culinary arts.

 

Tito’s Mexican Bar & Grill, winner of The Berkshire Eagle’s Best of the Berkshires award for Best Mexican Restaurant, is a family-owned restaurant offering burritos, fajitas, tacos, enchiladas, quesadillas, amazing margaritas, and many more Mexican-inspired dishes.

 

Ronny B., chef and owner of BB’s Hot Spot at The Lantern, will entice you with the home-grown flavors of his native Grenada, known as the Island of Spice. Savor the tastes of true cinnamon, nutmeg, mace, saffron, cloves, ginger, and cocoa in his jerk and BBQ specialties. Come in and taste the islands!

 

Sibaritas and Methuselah Bar and Lounge

Sibaritas has Italian flavors covered with homemade pasta and other Italian-fusion offerings on the menu, and Methuselah Bar and Lounge is a casual, rustic chic award-winning bar specializing in craft cocktails, craft beer, sustainable/organic wines, and succulent tapas.