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15 Food Favorites | Pittsfield, Mass

15 Food Favorites | Pittsfield, Mass

During my 15 years in the Berkshires, Pittsfield has been a city that’s grown on me the longer I’ve lived in the region. Over the past few years, I’m glad to have had a chance to meet with the chefs and people putting out food in the area.

For those visiting Pittsfield or the Berkshires, I put together a guide of 15 of my favorite food experiences. Whether you’re in town to visit a relative, on a business retreat, or attending one of the many cultural events, there are plenty of options to have a good meal in the largest city in the Berkshires.

Table of Contents:

  1. Coffee & sweet treats at Dottie’s Coffee Lounge (444 North St, Pittsfield, MA 01201)

  2. Burgers at The Lantern Bar and Grille (455 North St, Pittsfield, MA 01201)

  3. Milkshakes at Joannes Pittsfield Luncheonette (123 Elm St, Pittsfield, MA 01201)

  4. Cocktails at Methuselah Bar and Lounge (391 North St, Pittsfield, MA 01201)

  5. Bread at Berkshire Mountain Bakery Pizza Cafe (180 Elm St, Pittsfield, MA 01201)

  6. Frozen yogurt at Ayelada (505 East St, Pittsfield, MA 01201)

  7. Craft beer goodness at Thistle & Mirth (44 West St, Pittsfield, MA 01201)

  8. Tacos and margaritas at Tito’'s Mexican Grille (34 Depot St, Pittsfield, MA 01201)

  9. Coal fired pizza at East Side Cafe (378 Newell St, Pittsfield, MA 01201)

  10. Eggplant Parmesan at Mazzeo’s Ristorante (1015 South St, Pittsfield, MA 01201)

  11. Baseball eats at Wachonah Park (105 Wahconah St, Pittsfield, MA 01201)

  12. Craft beer to go at Chico’s Wine & Spirits (1245 W Housatonic St, Pittsfield, MA 01201)

  13. Vegan Eats at Thrive Diner (145 Wahconah St, Pittsfield, MA 01201)

  14. All things local at Downtown Pittsfield Farmers Market (The Common, First Street, Pittsfield, MA 01201)

  15. Ice cream at King Kone (133 Fenn St, Pittsfield, MA 01201)


#1 Coffee and desserts at Dottie’s Coffee Lounge

This North Street spot is the place to do in downtown Pittsfield for espresso drinks and sweet treats. I’m partial to seating by the windows, but really, any seat is good.


#2 Burgers at The Lantern

Grass fed burgers, meets local bar vibes. This is one of my favorite spots eat in downtown Pittsfield. Owned by Bjorn Somlo, he and chef Ray Stalker put an updated spin classic American and diner-style dishes. If you are vegetarian or vegan, go for the Carrot a la flat top.

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#3 Milkshakes at Joanne’s Pittsfield Luncheonette

A classic American diner in the Elm Street neighborhood of Pittsfield, this is the spot is not only a place to grab a short stack of pancakes, but to grab a milkshake!


#4 Cocktails at Methuselah Bar & Lounge

Located on Pittsfield’s North Street, this is the spot to grab a craft cocktail in downtown Pittsfield. A short walk from Barrington Stage Company, stop by Methuselah before a show or for a night cap!


#5 Bread at Berkshire Mount Bakery Pizza Cafe

While the bakery’s flagship location is in nearby Housatonic, the Pittsfield outpost is a spot where you can get all of the baked goods that Richard Boudon has to offer, including his famous Bread & Chocolate.


#6 Frozen yogurt at Ayalada

Family owned, and all the toppings! A short drive from downtown Pittsfield, grab a cone from their list of rotating flavors and top with with a range of sweet additions (from fresh fruit to boba and cereal!)

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#7 Craft beer at Thistle & Mirth

On the tail end of downtown Pittsfield, Thistle & Mirth offers about a dozen rotating taps, an extensive whiskey list and more. A casual atmosphere, bring a group, grab some brews and settle around a board game for a fun night in the Berkshires!

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#8 Tacos and margaritas at Tito’s Mexican Grille

If you’re looking for a low-key spot for tacos and margaritas Tito‘s is the place for you! They’re expensive lunch and menu options to offer something for everyone. Coming in for a weekday lunch? In my experience the service has been quick, service friendly and food hot.

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#9 Pizza at East Side Cafe

The East Side Cafe is a Pittsfield landmark and one of the few places one can get a coal-fired pizza. The Pizza toppings are simple — customers can build their own, or go for the local’s favorite: The Special with sausage, mushrooms, garlic and hot peppers. I’m a simple girl and go for pepperoni pizza all the way.


#10 Eggplant Parmesan at Mazzeo’s Ristorante

Thin layers of eggplant breaded and layered to make a small tower of sauce cheese that is the epitome of Italian-American comfort food. Eggplant parmesan is of of my favorite meals and Mazzeo’s does it well.


#12 baseball eats at Wahconah Park

Whatever team is playing at Pittsfield’s home stadium at Wahconah Park, grabbing a bite to eat will make the gam regardless of the score. In fact, baseball games are an inexpensive summer activity, super family-friendly and is a good thing to do when you don’t have anything planned for the evening.


#13 craft beer to go at Chico’s Wine & Spirits

Located on West Housatonic Street, Chico’s is worth a stop if you’re looking to stock up on your favorite brews for camping or are looking to get some craft beer recommendations while in Pittsfield.


#14 Vegan eats at Thrive Diner

While this is not the first time Pittsfield has had a plant-based restaurant,Thrive Diner is a good spot to know about if you are looking for vegan dining options in the downtown Pittsfield. Sourcing locally as much as possible and making much of their food in-house, for those vegans in the Berkshires, this is the place to grab a meal.


#14 Everything local at the Downtown Pittsfield Farmers Market

Looking to stock up on local produce and meats and local vendors? Check out to Downtown Pittsfield Farmers Market, organized by Roots Rising. Occurring every Saturday in the summer with indoor options in the winter, the Pittsfield’s farmers market features produce from local farmers all around the Berkshires, artisans selling their handmade wares and live entertainment and activities for the family. As you can see from the photo, I’m a pretty big fan.


#15 Soft serve at King Cone

A short walking distance from the Downtown Pittsfield farmers Market, King Cone is where you can get cheap soft serve on a warm summer night. This isn’t a place that you’re going to find 50 different flavors: they keep it easy for good reason. Vanilla with sprinkles for me!

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