Your guide to dining in Berkshire County

Opened in September 2021 in the former Rainbow Restaurant space on First Street, RJ’s Restaurant is the fourth dining concept launched by hospitality veteran José Reyes, who oversees front-of-house operations alongside his cousin and culinary partner, Chef David Reyes.

With more than 20 years of restaurant and catering experience in Long Island and New England, José Reyes brings a deep knowledge of upscale casual dining. He began his culinary journey training with the renowned Scotto Brothers before opening his own establishments, including Picante’s in Lakeville and Canaan (CT), and El Noa Noa in Chatham (NY). RJ’s is the latest chapter, combining his East Coast expertise with the welcoming charm of the Berkshires.

RJ’s offers a refined yet approachable take on American-Italian cuisine, with a strong focus on fresh seafood, handmade pasta, premium chops, and steaks. Signature dishes include lobster bisque, eggplant parmigiana, veal parmigiana, shrimp Alfredo, New York strip steak, and the ever-popular housemade chicken wings.

The dining experience at RJ’s is marked by its cozy and elegant ambiance, complete with white-linen table settings, friendly and attentive service, and a warm, relaxed atmosphere that continues to win over locals and visitors alike.

Whether you’re celebrating a special occasion or enjoying a casual night out, RJ’s blends big-city flavor with small-town hospitality—making it a must-visit culinary destination in Pittsfield.

An eclectic breakfast and lunch cafe located in the heart of the Berkshires, On a Roll Cafe and Catering Company has been serving fresh and exciting menu items for over 16 years. We strive to provide our customers with the highest quality food possible by making everything from scratch inhouse; from our salad dressings to our Sour Dough & 7 Grain breads to our Breakfast Sausages. Along with our tried and true breakfast and lunch menus, we have soup, frittata, and lunch specials that change daily. If you can't make it in for lunch give us a call! We deliver lunch with a minimum $25 order.

Located inside the historic Hotel on North, RARE 297 Steakhouse opened its doors to the public in the summer of 2024 and has quickly become Pittsfield’s go-to destination for elevated dining. Specializing in premium steaks, sushi and seafood. Rare 297 brings modern elegance and classic flavors together in the heart of the Berkshires.

Our signature dish—the Filet Mignon Oscar—is a guest favorite and a true reflection of our culinary craftsmanship. Guests can enjoy the convenience of online reservations and ordering, as well as an inviting atmosphere perfect for both intimate dinners and lively gatherings.

Cocktail Lounge & Banquet Space

After your meal, unwind in our stylish in-house cocktail lounge, where expert mixologists craft cocktails that pair perfectly with your dinner or stand alone as a reason to visit.

Rare 297 also features a private banquet hall with a capacity of up to 234 guests, making it an ideal venue for weddings, corporate events, birthday celebrations, and more. In addition, we offer conference rooms that can accommodate up to 49 people, perfect for meetings, workshops, and seminars. We proudly oversee several rental and event spaces within Hotel on North, providing full-service planning and coordination to ensure a seamless and memorable experience for every occasion.

Whether you're joining us for dinner, drinks, or a celebration, Rare 297 Steakhouse is proud to offer an unforgettable experience in the heart of downtown Pittsfield.