Whether you are trying to impress that first date, cozy up with your honey, take a night off from the kids or just head out for a night of fun (with or without romance on the table), it is important to pick the right combination of activities. With three hours to spend, you can enjoy some of the very best in Pittsfield.
Heed the call of the outdoors with a sunset picnic.
If the weather cooperates, there is nothing more impressive than watching the sunset over the Berkshire Hills. Layout a picnic dinner and you have a perfect way to see one of the best shows in the sky.
Start by picking up dinner and beverages at Guido’s Fresh Market on Pittsfield’s south side. It’s a popular one-stop-shop to get everything from cooked entrées, salads, cheese from around the world, side dishes, and wine or beer. Another option is to pick up a complete dinner for two at K. J. Nosh Catering Company. Its tagline is “Real Food Real Local.” They have weekly dinner specials like pesto shrimp tortellini and steak and pepper stir fry.
Take out a tasty BBQ platter big enough to share from Smokey Diva’s, the home of 92nd Sauce, which is sold at markets across the state and into New York. Their tender ribs, succulent brisket, or pork with just the right amount of pull taste great with their side dishes and peach cobbler for dessert. Or, try something a little different and thrill your taste buds with Caribbean food from B.B.’s Hot Spot with jerk or grilled chicken, jerk quesadillas, and other specialties. Enjoy with their homemade fresh Sorrel, a celebratory drink from the West Indies.
Picnic in hand, head out to any number of Pittsfield spots with a great view of the western sky. Burbank Park has a grassy knoll that points out into Lake Onota. Spread your blanket or sit at one of the nearby picnic tables and see the sun and its reflection on the water. Or, head to a spot near the top of the Pittsfield State Forest. The overlook near Berry Pond, which is the highest body of water in the state, provides a view of the sunset over three states. Or, set up near the Pittsfield Airport and watch the planes take off and land.
Dine in at a hip restaurant.
Kick-off a great evening of food and entertainment at one of three different restaurants on upper North Street that offer light bites and unique drinks.
The newly renovated Mission Bar & Tapas under chef Jeremy Berlin is known for its inspired set of small plates that can be shared with a glass of beautiful wine, beer, and cocktail selection. Berlin spent a decade working in Michelin-starred restaurants and an eight-year stint with renowned chef Gordon Ramsay in Los Angeles, New York, and Las Vegas. The food is a celebration of the bounty of the Berkshires and incorporates artisanal and seasonal ingredients into delicious combinations.
District Kitchen and Bar is hip and classy, without being pretentious. District serves a contemporary cooked-to-order American menu that changes weekly based on what is fresh and in season. From burgers and pan-roasted salmon to curry coconut vegetable stew and grilled Statler chicken, you won’t go wrong. It has an extensive wine, beer, and cocktail list. We advise making a reservation.
Enjoy a cozy dinner.
Escape to Italy for a night. Trattoria Rustica has an intimate ambiance with its brick-lined walls, candles on the tables, and images from Italy. Its wood-fired brick oven brings out ancient flavors from baked and grilled dishes. Savor amazing specialties and fine wines. Remember to leave room for dessert. We’ve heard songs sung about their chocolate bomba.
Have a romantic outdoor experience at the Proprietor’s Lodge Restaurant. From its beautiful deck on Pontoosuc Lake, you can see the sunset to the left and views of Mount Greylock, the highest point in Massachusetts, to the north. Or just watch the pleasure boats go by. Mazzeo’s Ristorante is well known by locals for its full Italian-American meals. You can get a complete dinner served on the outside patio. The restaurant is popular so be sure to make a reservation.
After a long workday, a night out at a pub-style restaurant can be the perfect date night meal. Patrick’s Pub is a local favorite frequented by regulars. Enjoy a variety of comfort foods, such as New England Clam Chowder, Jack Daniels® Tenderloin, chili, and fish and chips. Unwind with your date among the brick archways and wood-toned furnishings.
Then catch a show or live music.
Pittsfield is the home of more year-round entertainment than any other place in the Berkshires. There is almost always something going on.
Check out the live theater at the Barrington Stage Company or the Colonial Theater. Barrington Stage is known for its many award-winning productions that later make their way to Broadway. The Colonial Theater, part of Berkshire Theatre Group, one of the oldest theater companies in the country, brings in productions and music from around the world. Both theaters host shows all year-round. Check their schedules.
The newly remodeled Beacon Cinema offers heated reclining loveseat-style pods that allow you to be close to your date. They have a power reclining feature that provides virtually limitless relaxing positions. The theater shows the latest releases with wall-to-wall digital projection and immersive sound.
Live music venues abound in Pittsfield. You’ll find live music many nights of the week at Mission Bar & Tapas, Methuselah Bar and Lounge, The Flatburger Society, Patricks’ Pub, and Proprietor’s Lodge Restaurant.
Don’t forget to check our list of special events for live festivals, such as the fall’s Pittsfield Jazz Festival or the winter’s renowned 10×10 festival. Each Friday in the warm weather features First Friday’s Artswalk during which local artists and artisans open their studios to the public for a great evening.
The night is still young.
Keep the night going. One of the liveliest spots in town is the Zagat-rated Methuselah Bar and Lounge.
Some of the most knowledgeable bartenders in the area serve up craft beers, curated wines, and craft cocktails. They also serve local charcuterie and cheeses, specialty tacos (the portobello tacos with garlic aioli are amazing), and creative Korean bites inspired by the owner’s family heritage.
Across the street, Mission Bar & Tapas keeps things going late into the night and often features live music to finish off the evening.