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A great date night calls for a fantastic dining experience. Whether you are on a first date or the grandparents are babysitting for a night, there's nothing like connecting over a meal. Preparation is key, from choosing your best outfit to choosing the best restaurant. For date nights, look for a restaurant with an appealing menu, classy ambiance, and great service.
Experience Pittsfield’s Best Date Night Restaurants
Pittsfield is known for its focus on delicious and diverse cuisine. If you are looking for the perfect date dinner, you'll have no problem finding a restaurant with a great menu, comfortable ambiance, and exceptional service.
Dining at Hotel on North: Berkshire Palate
Berkshire Palate features a modern American menu. It uses the freshest ingredients and focuses on local sources for the best farm-to-table experience. Berkshire Palate believes that food isn't an afterthought but an integral part of our lives.
Berkshire Palate's menu is seasonal to ensure the freshest ingredients. For example, during the summer, the restaurant offers several summer farm harvest options such as Radish & Butter, Broccoli & Honey, and Burrata.
Main plates include Local Steaks, Lamb Lollipops, Grilled Swordfish, and Cavatelli Gratin. In addition, Berkshire Palate serves beer, wine, and cocktails.
Located at Hotel on North, Berkshire Palate has a beautiful design with exposed brick walls and gorgeous artwork. If you’re visiting the area be sure to check out our beautiful Hotel on North rooms.
Cafe Triskele
Cafe Triskele is a French restaurant that serves homemade dishes in a delightful, cozy atmosphere. French restaurants are known to be romantic, and Cafe Triskele will ensure your date night is perfect with delicious food and attentive service.
Cafe Triskele is run by a husband and wife team focused on crafting comforting and delicious food that will keep you coming back time after time. The owner-chefs work with quality specialty suppliers and local sources. In addition, the cafe focuses on using organic ingredients as much as possible. The menu features gluten-free items, heirloom vegetables and grains, and daily specials.
For starters, try the Escargots a la Bourguigonne or French Onion Soup. Entrees include Crispy Duck Confit, Surf & Turf, and Cod Casserole. Guests can try craft beer, house cocktails, or choose from the extensive wine list.
The restaurant has three welcoming dining rooms and a summertime outdoor porch for the perfect date night dinner near Pittsfield MA.
Mazzeo's Ristorante
Mazzeo's Ristorante serves Italian-American meals. For a special treat, enjoy dinner on the outdoor patio. Mazzeo's is family-owned and has a warm and elegant ambiance.
The menu features all your favorite Italian dishes such as Eggplant Parmigiana, Lasagna, and Gragranelli Di Mia Carbonara.
Mazzeo's also has a gluten-free menu and an extensive dessert menu. Save room for House-made Tiramisu, Chocolate Lava Cake with Vanilla Ice Cream, or Cannoli. If you want to impress your date, order the Chocolate Piano with Rasberry Mousse.
Mazzeo's has an extensive wine list, so you can pair the perfect wine with an exceptional meal.
Prime Italian Steakhouse and Bar
Prime Italian Steakhouse and Bar has upscale indoor seating and refreshing outdoor seating. The menu focuses on exceptional Italian dishes and Prime meat cuts. Start with Sweet & Spicy Calamari, Caprese, or Bruschetta.
Entrees include classics such as Veal Marsala, Pasta and Meat Balls, Filet Mignon, and NY Strip. Prime Italian also has a vegan menu with dishes like Pasta Primavera and Arugula Salad. Try Limocello Mascarpone Cake or Italian Tiramisu for dessert.
RJ’s 109
RJ's opened in 2021 and brings fresh energy to Pittsfield's restaurant scene. All the food is prepared in-house and made to order. The menu has classic Italian items and seafood dishes. RJ's has an upscale interior, exceptional service, and live music.
Dishes include Musells, Baked Clams Oreganatta.
To impress your date, try the massive Two-Tiered or Three-Tiered Seafood Tower. RJ's serves all your favorite traditional Italian pasta dishes, Free Range Chicken, and Bone-in Rib Eye.
This classy restaurant is the perfect place for a date night.
Experience Pittsfield’s Hospitality
Date night can be fun, exciting, and nerve-racking. However, dining at one of our favorite date-night restaurants will make planning easier. Just remember to save room for dessert!
