Highland, an esteemed American restaurant nestled at 100 Fenn St in Pittsfield, MA, has garnered a loyal following since its inception in 1936. The warm and inviting ambiance mirrors the charm of a family-run establishment where comfort food reigns supreme. Customers frequently rave about the homemade dishes that deliver both satisfaction and nostalgia.
Duke Avearl highlights the enticing buffalo wings, praising their unique sauce that stands out from typical offerings. AnnMarie echoes this sentiment with her commendation of the Chicken Parm, which she describes as hearty and perfectly cooked, draped in an exquisite old-world sauce. Meanwhile, Don M's touchstone—the veal parm & spaghetti—is a family favorite, complemented by the best bread in the county. The portions are generous, making it a fantastic spot for family dining, as noted by Lincoln Wettenhall.
Service is generally attentive, with friendly staff members enhancing the experience. Although some reviews mention occasional service hiccups, the fantastic food makes it more than worthwhile. Highland's legacy as a beloved local spot shines brightly, inviting newcomers to savor a piece of Pittsfield history. It's an ideal destination for those craving timeless, flavorful American cuisine.
Amenities and More
Accessibility
Has wheelchair-accessible car park
Has wheelchair-accessible entrance
Has wheelchair-accessible seating
Has wheelchair-accessible toilet
Service options
Offers takeaway
Serves dine-in
No delivery
Highlights
Serves great cocktails
Serves great coffee
Serves great dessert
Good for watching sport
Popular for
Popular for lunch
Popular for dinner
Good for solo dining
Offerings
Serves alcohol
Serves beer
Serves cocktails
Serves coffee
Serves comfort food
Serves food
Quick bite
Serves small plates
Serves spirits
Serves wine
Dining options
Serves lunch
Serves dinner
Serves dessert
Has seating
Amenities
Has bar on site
Has toilet
Atmosphere
Casual
Cosy
Historic
Crowd
Family friendly
Good for groups
Popular with tourists
Planning
Accepts reservations
Payments
Accepts cheques
Accepts credit cards
Accepts debit cards
Accepts NFC mobile payments
Credit cards
Children
Good for kids
High chairs available
Has kids' menu
Parking
Free of charge street parking
Free parking lot
Paid parking lot
Paid street parking
Plenty of parking
Photos
Reviews For Highland
Duke Avearl
Jul 2,2025
The food was yummy and satisfying. I got some buffalo wings and the sauce was good and didn't just taste like they used a bottle of Frank's, not that I don't like Frank's, but I like restaurants to do there own unique sauce as well. Got the eggplant parmesan as well and it was pretty basic but gave me what i wanted. Got this as takeout and it was securely packaged. The lady that brought me my food was friendly.
Don M
Jun 20,2025
Family favorite. I always get veal parm & spaghetti, never disappointed. Also recommend the scallops. Service has some issues at times but it’s hard to find good help these days, not to mention enough good help. The food makes up for all. Also best bread in the county.
Kevin Sullivan
Jun 15,2025
What a wonderful place. Reminds me of one of those places my parents took us when we were kids. Easy to understand why they have been in business so long.
Lincoln Wettenhall
Jun 10,2025
Terrific local spot in Pittsfield. Family size portions here and great service. Sausage, Peppers and Onions with Spaghetti was great here and some left for later on. Been open since 1936 and the there was definitely a strong regular presence a good sign.
AnnMarie
Jun 7,2025
While the outside is quite unassuming, the interior is an inviting, comfortable atmosphere. The staff is super sweet. Our server Jackie was full of smiles, I wanted to hug her! She made our night. The food was like homemade comfort food. I ordered the Chicken Parm, and I loved it. Chicken was hearty and tender, perfectly breaded and fried without being heavy, smothered in mozzarella. The sauce is a simple old-world style that compliments the chicken perfectly. Pricing and portions were on point. Would highly recommend for a charming datenight.
Scott C
May 29,2025
Been coming here since a child. Love the food and atmosphere. Plates were piled full and we left stuffed! AAA Veal Parmigiana was great! Italian sausage Parmigiana was great! Wife's roast beef was 3 inches thick and delicious also!
John Kruszyna
May 28,2025
Always enjoy a great lunch with reasonable prices. We enjoy the hot veal parm, eggplant parm and chickem parm open faced sandwiches smothered in thick sauce.
Paul Oleskiewicz
May 15,2025
A family owned business where one of the owners will come out to greet you no matter how busy it is. The food is amazing and the portions are huge. Definitely a place I would recommend to anyone who loves home cooking where you're treated like you're part of the family
Reviews For Highland