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Highland Restaurant

100 Fenn St, Pittsfield, MA 01201-6230
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Ranked #31 of 152 Restaurants in Pittsfield
Tue - Sun 11:00 am - 9:30 pm
Cuisines: American
Most recent review
- Jun 19, 2014
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13 reviews from our community

Visitor rating
Rating summary
Date | Rating
  • English first
  • Any
English first
Waltham, Massachusetts
Senior Reviewer
6 reviews 6 reviews
4 restaurant reviews
4 of 5 stars Reviewed June 19, 2014

The Highland has been in business for many years -- even before I was born. It is one of those great old Italian restaurants with good spaghetti and meatballs. Career waitresses are always the best and the Highland has them -- they know that menu backwards and forwards. It's not fancy, but it's definitely worth the trip.

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Pittsfield, Massachusetts
12 reviews 12 reviews
10 restaurant reviews
2 helpful votes 2 helpful votes
2 of 5 stars Reviewed March 10, 2014

I have eaten there a couple of times and was just there last week with our friends. They do a great business but I really don't understand why. Everything about the place along with the food is medicore. Waitstaff and the hostess are friendly enough, but everything elso is surely lacking. I had the pot roast and it was horrible.... More

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Top Contributor
97 reviews 97 reviews
46 restaurant reviews
32 helpful votes 32 helpful votes
4 of 5 stars Reviewed October 11, 2013

Where else could four people go for lunch for $30 including tip & tax? My husband raves about the Spaghetti and sausage and ALWAYS orders TWO sausages! (it usually comes with one) Family owned for 77 years and consistently good predominately Italian fare. What they call Vienna bread is more what I'd call Italian and is from Pittsfield Rye ...... More

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Dalton, Massachusetts
Senior Contributor
24 reviews 24 reviews
20 restaurant reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed August 21, 2013

Small neighborhood restaurant and bar. Menu has old time favorites. They are REALLY great about addressing food allergies. Every time we have dined there, each server listened and assured our meals were prepared to guarantee a safe experience. From meatloaf to sandwiches and daily specials, you will be reminded on meals that were made when you were a kid.

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Top Contributor
63 reviews 63 reviews
51 restaurant reviews
17 helpful votes 17 helpful votes
5 of 5 stars Reviewed August 10, 2013 via mobile

My husband has been going to The Highland since he was a baby. We go about 3 times a month. This is a place where everyone knows you and at least one of the Arace brothers will come out of the kitchen to say hello and ask how you and your family are doing. My favorites on the menu are... More

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Top Contributor
50 reviews 50 reviews
39 restaurant reviews
20 helpful votes 20 helpful votes
5 of 5 stars Reviewed July 16, 2013 via mobile

Try this restaurant if you are looking for genuine good home cooking. Try the chicken parm and spaghetti. Delicious every time. Comes with a small salad and fresh bread. Reasonable pricing but cranky waitresses that have worked there 20years too long.

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Windsor, Massachusetts
1 review
5 of 5 stars Reviewed May 18, 2013

Have been going to the Highland with my family for years. When our out of state relatives come into town, it's the first place we go.

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Pittsfield, Massachusetts
Senior Contributor
45 reviews 45 reviews
28 restaurant reviews
10 helpful votes 10 helpful votes
1 of 5 stars Reviewed April 7, 2013

Worst sauce, tasted like ketchup. Pasta is horrible, no one should eat here ever, food is cheap and you get what you pay for.

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Williamstown, Massachusetts
Top Contributor
64 reviews 64 reviews
49 restaurant reviews
34 helpful votes 34 helpful votes
5 of 5 stars Reviewed November 20, 2012

The Highland always delivers on its promise to provide a wholesome, hearty meal at very affordable prices. It is not gourmet, nor does it want to be, but it provides an honest, stick-to-the-ribs, satisfying meal with generous portions in a relaxed environment. Some may describe it as a family restaurant, but I have yet to suffer the screams and shenanigans... More

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Pittsfield, Massachusetts
Senior Contributor
30 reviews 30 reviews
23 restaurant reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed November 18, 2012

The spaghetti is popular with plate after plate passing by but my favorite is the roasted pork tenderloin. It is tender, moist, and lean. I don't believe it's on the menu on Fridays though. And keep in mind they are closed on Mondays. I've heard their onion rings are great and I plan to order them next visit. The restaurant... More

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