8 Best Bars in Pittsfield

Mazzeo's Ristorante Italian • $$
1015 South St, Pittsfield

Customers` Favorites

Chocolate Lava Cake with Vanilla Ice Cream
Chocolate Piano with Raspberry Mousse
Chicken Parmigiana with Cavatelli
Vanilla Bean Creme Brulee
Linguini Zuppa Di Pesce
House Made Tiramisu
Fettuccini Alfredo
Chicken Francese
Calamari Fritti
Marsala

“We had an awesome meal! The food was just delicious, the staff was amazing and we will be coming back the next time we are in town. We have always driven by and never thought to give Mazzeo a try. So glad we did!----FYI - We had another trip to the Berkshires (most notably Jiminy Peak) but made sure we made reservations to Mazzeos again.“

4.2 Good123 Reviews

2
Teo's

Teo's Hot Dogs • $
1410 East St, Pittsfield

Customers` Favorites

2 Hot Dogs with Sauce and Cheese Cheese Tater Tots
Hot Sausage Patty Sandwich
French Fries Tater Tots
Teo's Hot Dogs
Cheeseburger
Hamburger
Chili Dog

“I didn't know Yelp went through GrubHib, sorry! I do not usually eat hot dogs or raw onions but something about these little bun wrapped wieners just speaks to my soul. I drive an hour occasionally to get a few of these. Love this spot.“

4.3 Superb68 Reviews
Methuselah Bar and Lounge Wine Bar • $$
391 North St, Pittsfield

Customers` Favorites

Pigs in a Blanket
Marinated Olives
Chicken Tacos
Korean Kalbi

“We were traveling and spending the night at the Hotel On North. They recommend this place for a drink and it did not disappoint. We had the cheese board with drinks and then came back after dinner. The bartenders were great! We will be back.“

4.1 Good60 Reviews
Jae's 7 Winter American • $$
7 Winter St, Pittsfield

Customers` Favorites

Country Style Mashed Potatoes
Fried Chicken Wings

“We had the pleasure of dining at Jae's twice in recent months. On both occasions, we were indeed very fortunate to have Brian as our server. Brian was friendly and welcoming, and he made us feel at home due to his positive energy. Food-wise, the highlight of my dinner on the second occasion was the Jae's Special Roll - delicious! We will be back, and we will ask for Brian.“

4.1 Good39 Reviews
Thistle & Mirth Bar • $
46 West St, Pittsfield

Customers` Favorites

Chashu Pork Belly Ramen
Mushroom Banh MI
Marinated Egg

“Found this place while briefly passing through Pittsfield on a recent Saturday afternoon. Immediately struck by the lived-in charm, character, and vibe of the place. Unfortunately 99% of the bars in Boston were built brand-new over the last 30 years and try to be all things to all people. Loved people watching the regulars at the bar and hearing cool retro rock on the speakers (as others have remarked: at somehow JUST the right volume).Also, the waitress/bartender was very friendly and welcoming to me and my two young daughters, even if they probably weren't in the typical age of the clientele.Had an early dinner of Ramen which was also delicious and very filling for the price. Would definitely come back here if I pass through the town again.“

4.1 Good33 Reviews
Crossroads Cafe Bar •
195 Onota St, Pittsfield

“Can there be some sort of vaccination karaoke night lol. 5 years ago the last time I went there it was awesome I don't drink but it was cool to hang out with all the local townies everybody was cool there as long as you're an alpha male but I would really like to see some karaoke“

4.3 Superb9 Reviews
Italian-American Club Bar • $$
203 Newell St, Pittsfield

“...we are very blessed that my daughter can have her wedding be the "first event back" at The Italian American Club since the covid 19 outbreak...the hall is beautiful...and we couldn't happier with the inhouse catering...everything is just perfect...highly recommend any event to be held there...❤“

4.3 Superb7 Reviews
Sideline Saloon Bar • $$
434 Fenn St, Pittsfield

“I've been in search for a great old throw back feel to Brooklyn Irish pubs. The great pubs are usully Irish ones. I found sideline and I must say with in minutes I felt a level of comfort. The owner Colleen was smart and engaging , fun to talk with.The GUINESS was the highlight for my husband it was perfect. There was no food but that didn't matter. The best Irish pubs have no food and offer good conversation and,the customers were filled with good conversation. I love this place. I will return to listen to their music when they have music. First time there but not the last time there. I was beginning to lose hope in finding a good Irish pub.I can't wait until football season to catch a game. They promised us the Steallers !! LolGreat establishment.Annie“

4 Good10 Reviews
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