We visit here as a family ritual for someone's Bday. Been here forever, mostly padded booths, old school vibe. Extremely locally popular with very personable + attentive waitresses who have been working here forever + know their stuff. Full bar, and mainly Italian menu but with American mainstays(roast turkey dinner, burgers,etc). I'm not a big Italian meal fan- but they're also known for their phenomenal fried scallops (app or dinner/either gives you about same amount). Also, pretty good portion size. Finally good, decent sized salads and really great blue cheese dressing. Everything about this place is good+ reasonable- it's casual, comfortable + home cooking- but not high end. read more

I started going to the Highland as a little girl in the 60s. I love that it still feels old school. When Pasquale is behind the bar he always welcomes you by name. The waitresses have been there forever and are friendly, quick to wait on you and happy to work there. My husband always gets the sausage and peppers and I always get the scallop sandwich. Best in town! read more

Good food,friendly staff nice atmosphere. Locally owned by same family since 1936. Definitely will go back

My husband used to go to the Highland as a kid growing up in Pittsfield. He hasn't been there since, so when the Berkshire Eagle did a story on the Highland, we said "Let's go." And, we weren't disappointed. He had the Buffalo wings, an order of fries and a beer. I had the Italian trio (side salad, sausage, meat ball and chicken parm, plus what looked like a half a box of spaghetti.) The blue cheese dressing that came with his wings, and which I also got on my salad, was the best we have ever had. It was rich and creamy and had huge chunks of blue cheese in it. Celery with the wings was fresh. Didn't look like it had been sitting around forever. Everything was delicious, and we took tons of food home, including 4 huge slices of Italian bread that we hadn't even touched. Total before tip for the two of us was $54. This is definitely going to be one of our favorite restaurants from now on. read more

the BEST meal i've ever had in my life. been coming here consecutively for 26+ years, use to refer spaghetti as "highland". do yourself a favor and stop into this gem/staple of Pittsfield! amazing service, owner, and ambiance. the bread is to die for, and the fried chicken dinner is a must every time I visit home! read more

Highland Restaurant - fried chicken dinner - Italian Near Me - Pittsfield, Massachusetts

My Highland restaurant has been a staple of Pittsfield Massachusetts for more than a half a century. The food is always fresh and very well done, service is extremely nice the service make you feel like they know you for years the ambience is very clean and nothing to write home about but with good food and a great staff, I think we can all overlook that part. read more

The Highland, for 50+ years you know what you're going to get, good old school Italian food, in a nice old school setting. The food has been good and consistent since I was a kid. They always have many homemade pies for dessert as well. One of my favorites is the broiled mushrooms and spaghetti or fried scallops. The wait staff is always friendly. The owners are not just owners, the entire family works there from the kitchen to the bar to running the floor. You will always get a hello how have you been followed by a we really appreciate your business on the way out. What more can I say, we eat there usually once a week. THANX read more

This place always delivers a solid old school meal. I don't think it's too clean by any stretch of the imagination but the service is friendly and the pasta sauce is great! read more

Stopped in on our way to see the leaves change in VT and NH. So glad we did--this place is a gem! Wonderful meal, wonderful service, and the owner took time to stop by our table to chat. Everyone--staff, customers--were so friendly. The portions are amazing and huge--we took home enough for lunch tomorrow. I had scallops with a side of spaghetti and salad with house Italian dressing (yum!) Hubby had chicken parmigiana with spaghetti. We shared an order of mozzarella triangles. Everything was delicious. Apparently this is their 88th year in business--I can see why. Hope our travels bring us back this way!! read more

Highland Restaurant - Mozzarella Triangles - STUFFED w/mozzarella! Yum!! - Italian Near Me - Pittsfield, Massachusetts

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Awesome food, and they had the best waitress of all time Mrs. Sharon Dewey. Been going there since I remember 1971 ish best Western Sandwiches hands down. read more

Good food. Good service. Feels like you are back in the 1960's when you're there. No computers. Personal service. A little slower than basic restaurants today reasonable prices. read more

My husband and I stopped in for dinner while in town visiting family. We've always heard great things about this restaurant, and it did not disappoint! The restaurant was busy for a Tuesday evening. When we walked in the door, were greeted by the owner and taken to our table. Our waitress was friendly, and efficient. I had the chicken Parmesan, and he had the manicotti. Both meals came with a salad and bread. Both were DELICIOUS ‼ This will be a regular stop for us every time we are in town! read more

The best plate of food you can get around amazing always 10/10 warm hot and delicious every meal

Brought my girlfriend here for her first experience of Highland love. We were both amazed at the size of the portion and flavor of the corned beef and cabbage dish. I also had the balboa sausage wrap. Everything was hot and delicious and served quickly. We talked to 4 or 5 really friendly employees and Pasqale himself one of the owners. Incredible food at hard to believe low prices. Don't miss it. read more

What a long time stable in the city. 86 years staying true to their routers. Family own delivering good food at a reasonable price. Staff super friendly. If your in the area you gotta give this place a try. read more

Food was very good and served nice and hot , the bread was very fresh , service was good, it's very comfortable

My favorite chicken parm in the Berkshires, paired with the coconut cream pie for dessert!

Absolutely terrific everything you want in a hometown Italian joint I recommend the chicken Parm the eggplant Parmesan and they have one of the most underrated chicken wings in town read more

Very authentic American restaurant - Old-Style interior, friendly staff and a cuisine that claims to have some Italian influence (Hope that they never get real italian guests...) Beer selection is limited to megabrews read more

Highland Restaurant - Italian Near Me - Pittsfield, Massachusetts

We went for dinner last Friday night after reviewing many options on Yelp. We knew from the reviews that it was an 'old-time' Italian restaurant and we were not disappointed. The chickenparmspaghettiandsalad was excellent. The chicken was tender and the breading crisp. The salad was cold and fresh. The bread was fresh and served with butter. The italiansausagespaghettiandsalad was also excellent. Lean and spicy sausage with plenty of pasta and the sauce was tasty. The service was friendly and efficient. Customers were friendly too - our waitress Charlotte gave us a great tip to go to Mt Greylock on the weekend - which we were very glad we did! read more

If you want a low key atmosphere and an affordable, home cooked, delicious meal this is the go-to. The restaurant is a staple in the Pittsfield area and it's easy to understand why. The service is excellent and the staff treats everyone like family. The food is really good and they have weekly specials if you're looking to mix up the regular Italian dishes (though they are delicious!) No need to make a reservation or dress up. It's like popping into your moms house for dinner. It a perfect local spot. read more

Highland Restaurant - Spicy scallop special - Italian Near Me - Pittsfield, Massachusetts

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What can I say? This place has been around much longer than I have been, and I hope it continues to do so. If your looking for fine dining and gourmet food, you will have to go somewhere else. The Highland is consistent old fashion style Italian food. The spaghetti is not "al dente", it's more the like what Mom used to make, thick and a bit mushy. The house red sauce is a thick, meaty tomato sauce that's not to heavily seasoned, in other words... a bit flat. I got the old stand by veal Parmesan & spaghetti. It comes with a house salad, nothing fancy here... iceberg lettuce, cabbage, carrots and onions (optional). The house dressing is a simple Italian style ( oil, vinegar and some basil) but all in all verytasty. The salad is still served in those old wooden bowls, bringing back memories. Now the veal parm is not a select piece of milk fed veal, pounded thin, and dredged in panko. It is a machines formed meat patty that is frozen until its deep fried in the Highland kitchen., I mean what do you expect for $12.95? The patty gets covered with a slice of cheese and smothered in the meat sauce (Mom would get hers covered in brown gravy). Once again... not fancy, but tasty. I can't forget to mention that all meals are served with very fresh Vienna bread, sliced thick and served with real butter. Now onto dessert. I was lucky tonight that they had their famous "grapenut" pudding! A delicious custard pudding with a maple flavor. It has a very nutty flavored layer on top that will curl your toes. Puddings are always served with real whipped cream. If the grapenut is not available, the cornflake pudding is a close 2nd. So I leave tonight with a full stomach, $20 lighter in my wallet and a little heartburn, but so worth it. The Highland is a great dinner spot in downtown that's been around for 82 years. Good food, decent prices and even a sit down counter for those who choose to dine solo. Tonight I sat at the counter and a visiting stage actress sat next to me & told me it was here 3rd visit to the Highland this week. A few months ago, I ran into my old school teacher from 30+ years ago. It's a great hometown place to eat that's more and more difficult to find in these days of organic and vegan trends. You can't go wrong with " good American fare" read more

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Have been coming here for 50+ years and it is consistently the same as ever. Family restaurant, warm, friendly, honest food. It is comfortable and predictable. You'll either get it and love it or not. It's really an institution and cares for a lot of people like a family would. read more

Worst experience ever .... ordered take out and arrived was told 1/3 of the entire order was unavailable.... received cold greesy soggy food 40 dollars for two horrible meals the fried shrimp smelled like 10 day old dead fish and the turkey sandwich was cold and tasted like really bad deli meat....never will go again waste of hard earned money better off tossing the money out of a window while driving past there to a better spot read more

I've been coming here for forty plus years.... this was where my family came on Saturday nights. It is a blast from the past. It is more diner-ish then fine dining so set your expectations accordingly. There is a good chef in the kitchen that offers up Highland classics plus some really great specials. This is a favorite in my office, too. Scallop sandwich, veal Parmesan sandwich, spaghetti and sausage dinners are all good. Beef stew on Wednesdays and Corned beef on Thursdays. It's affordable and family owned. One of our all TMNT favorites for a quick dinner without a chain name. So tired of the chains. read more

This place is an old favorite for the locals. My father grew up in Pittsfield, and I can remember coming here as a child when we visited his family. The place has not changed since I've been coming here. The last time I went was my first time here in 11 years, and it was exactly the same. I think the prices were too! My all-time favorite is the spaghetti and meatballs. Extremely huge portion for a very fair price. The sauce is excellent and the noodles were cooked perfectly. The meatballs as others have pointed out have a "unique" flavor to them. I've seen other ratings calling it dog food or simple beef puree, so all I will say is that they are "unique". For me, it reminds me of my childhood and brings me a sense of nostalgia, so I like them. They do somewhat have a puree taste to them, but that's not indicate that they taste bad. Honestly, you will either hate them or love them as they don't taste like typical meatballs. The salad and bread were fresh and great as well. Luckily for me, I had a business trip in CT recently, so I was able to come visit my father's side of the family over the weekend and got to come to The Highland again. Since I've always ordered the spaghetti and meatballs, I decided to try something different. Based on the great reviews of the veal parm, I ordered that which I admittedly was disappointed with. I sat at the counter and could see into the kitchen. The veal parm is a perfectly oval frozen patty thrown into the deep fryer and covered with a single piece of sliced cheese that looks processed. Where's the fresh mozzarella??? I ate it and it was ok, but after seeing how it was prepped, I felt cheated. I always thought of The Highland as having family recipes made from scratch, so I was extremely disappointed to see them using frozen ingredients now. The sauce and spaghetti were still on point though, and saved the dish. You get what you pay for I guess. If you want to feed the family at a reasonable price, give them a shot. Even though the veal parm gets a D, the spaghetti and their sauce are up there with the best I've had. read more

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I love this place. Isn't that enough? No...ok, so you want to know why? We've been going the highland since I can remember, and we've taken our children since they can remember. The wait staff has been there for years, and they treat you like family. The dark paneled walls are comforting, as are the old red booths with their charming dark faux-wooden tables. This is as real as it gets baby! Down home, down-town, and down-right. Is that too cliche for you? Then this isn't the place for you. Us townies...we could care less. Good food, good friends, good god...LETS EAT! Favs: Spaghetti w/Meatballs (Like pate rolled into a ball) Spaghetti w/Southern Fried Chicken Open faced Turkey sandwich, gravy, cranberry, mashed potato...the works! Scallop sandwich Chicken parm (when they have it) All come with salad. Used to be a better deal....used to come w/ house wine and salad. That's my only complaint. Otherwise I would have given 5 stars. :) read more

Oh my God. It's still the same!! I love this place. My parents used to take us here when we were kids and we would always order the same thing: Vealcutletparmigianaspaghettisalad. And it still tasted just like I remembered it. Oh rapture! This is as authentic as Italian-American food gets, which is why Mario Batali makes the crucifix sign with his forefingers whenever you mention it . Great red gravy and to-hell-with-al-dente spaghetti served to a discerning townie crowd. What's not to like? read more

For the price of the food this place does ok. Portions are very filling and the atmosphere is very relaxed. I'm big on good tomato sauce, and this rates up there on my list. I've been half a dozen times or so for dinner, and it traditionally is an older crowd. read more

You just have to appreciate the 1936 decor! The food is so good! Straight up Italian! Vienna bread, salad with homemade Italian dressing! Nice meat sauce. Great service and great prices!! We were here Saturday for lunch and had a great time watching the locals and college football. It's fun and funky...be prepared to step back in time. read more

Highland Restaurant - Italian Near Me - Pittsfield, Massachusetts

Pros: Quick service, nice staff, very townie Cons: My burger was pretty dry and the meat was a little grainy, I can say it was one of the worst burgers I've ever had. Even at the peak of dinner time with the place being backed, there was a strong odor -- not sure what kind, there was bleach mixed in there and it was extremely unappetizing, I was happy that the service was so quick because I was ready to leave as soon as I sat down and smelled it. Yuckkk. read more

Always a good meal at excellent prices. The service is always perfect. Where else can you get a filet mignon for $15? read more

Highland Restaurant - a man sitting at the bar - Italian Near Me - Pittsfield, Massachusetts

The atmosphere is dark and littered with paintings/pictures of baseball stars and memorabilia. This place would be scary at night. Here's why I like The Highland. It's a homey restaurant. People treat you as if they know you and welcome you with big smiles. The service is always quicker than you expect. The food experience is a unique one. If there were a spectrum from crappy food to gourmet, the food at The Highland wouldn't be on it. It's on its own plane of existence. It's on that plane of home-cooked that many institutions try to tap into but always inevitably fail because it's an untouchable realm. The Highland is a portal. Bare with me, this is hard to explain but very specific. You'll start with bread and a salad. Upon seeing these guys, you might think "that's it? this looks like it came from a frozen dinner plate." If you think that it's because you looked at the food. BUT you'll find that it's strangely better than some of the fanciest bread and salad that you've had. Like..."this isn't good - but I really like it". Or maybe I'm insane and most people simply call it "good". Your meal will unimpress you upon first look in the same way. The size is big. The smell is good. But you can't help but look at your veal parm (what I always get) and think "that looks like plastic". And they place it smiley in front of you and ask you if you need anything else. No, thanks. And you look over your meal again. It smells so good! And the cheese is melted just right. It just looks like rubber. Strange. Saw a bite off with your fork and it crunches through the breaded meat as easily as unfastening crossed Legos. Dip it in the balloon-colored sauce. And it tastes amazing. The noodles' texture is like nothing you've enjoyed before. Like they were made from some sort of sculpting material. The sauce has so little meat you'd think it was from a rainbow-colored can. But somehow it's perfect. In one sentence: The food at The Highland may throw off some diners by it's unique presentation but never fails to please through flavor in much the same way a meal at a new friend's home can be. My mom swears by the scallop sandwich to the extent that they make the correct assumption that she'll be eating it every time we go. Also: Order some pie. read more

This is a genre that is rapidly disappearing from the American landscape: The local, family-owned restaurant where you see the same folks frequently, and it feels good to be a regular. The Highland is an Italian-influenced, comfort-food, family-friendly place, where the food is plentiful, the cocktails are realistically priced, and the check won't bust your bank account. Uniquely flavored home-style meals will surprise the newcomer, and give truth to the oft-heard argument that Italian families all had their own way of making things. Departing from the Italian parts of the menu, you can get a great strip steak, the freshest of fried scallops, or juicy pork chops. Fantastic hand-breaded fried onion rings come in one size only, a large plate for sharing, which makes a great appetizer with conversation and drinks before dinner. Weekday specials are worth a look, as is the revised menu insert with items this place never used to offer, such as wings, prime rib, and Marinara sauce (the house sauce is a mildly spicy meat-based sauce). Nice pies, custards, and other dessert choices, too, if you still have room. You will eat large quantities of good homestyle food for relatively small amounts of money. read more

very nice people, great service, and food is great. If you're looking to get a classic burger and fries, this is where its at!

As you will see....the staff is great and on point. The food on the other hand is best left for senior citizens. The food is bland and tasteless... and unfortunately comes in big quantities.. I swear the meatballs are nothing more than ground beef puree, shaped into a ball and baked. The flavor and texture are morally repulsive. If you need to take your grandparents out to dinner, it's great.... but, if you want a real meal, there are tons of better places out there! read more

I came here while on vacation. Off beaten path for travelers but worth it. Great local restaurant with awesome friendly service and great food. If I lived near here I'd be here every day read more

Awesome food and great service by Sarah!!!! The chicken parm is very homey and everyone was so nice and accommodating!

Awesome food...chicken parm is the best ever...great homemade pies...great family place with great atmosphere, the owner was there working the bar welcoming most customers by name...we sat right across from the counter and he personally checked on us and everyone else a number of times...overall a great experience read more

Persuaded by a positive review, my best friend and I ate here. We are both mid-twenties but look young and the first thing our waitress asked was if we'd be looking for separate checks (not, for example, "How are you doing today?") We ordered their "award winning" buffalo wings for an app which were not really even buffalo but instead in some sort of sweet teriyaki sauce. When we mentioned that to our waitress, her response was "Oh, I don't know." Then my salad came, THEN bread and butter which is generally the first thing to come after you've been seated. As promised by that other review, it was fairly cheap and the portion was pretty big, but I would happily have taken quality over quantity here. The "homemade, cooked for hours" sauce that sounded so enticing could easily have been from a can and I'm betting that the line forming out the front door was only due to the scarcity of dining establishments in the area. I regard this as the worst restaurant experience of my life. read more