Highest-rated restaurants with outdoor seating in Pittsfield by diners

The average person spends over 74 minutes eating and drinking on any given weekday. On weekends and holidays, that goes up to over 81 minutes. Where is a better place to spend that time than a restaurant?

Consumers agree. The National Restaurant Association states that 9 in 10 adults enjoy eating out at restaurants, which give people access to a world of great-tasting food that's often difficult to reproduce at home.

People choose restaurants to scope out the latest food trends, including deeper dives into Southeast Asian cuisines from Korea, Vietnam, and the Philippines, without trying to master these complex dishes at home. Chefs also have the resources to experiment with ingredients and bring new favorites like hot honey, spicy maple, matcha, and pickled foods to the table.

Dining out also offers unique, hyperlocal experiences featuring local farmers, food producers, brewers, winemakers, and distillers in a way that connects diners to the area.

When the weather's nice, diners flock to al fresco seating. At least 2 in 5 diners like eating outdoors and look for great ambience like skyline views, rooftop settings, and waterfront seating to enhance their dining experience.

Stacker compiled a list of the highest-rated restaurants in the Pittsfield area using data from Yelp. Data is as of Aug. 4, 2025. Only businesses marked as having outdoor seating on the Yelp website were included. Yelp's ranking system calculates an adjusted rating value that considers the number of ratings and the rating score itself. Only businesses with at least 20 reviews within a 10-kilometer radius of Pittsfield were considered. Also, in an effort to highlight independent businesses and local chains, those with more than 10 locations nationally, based on our Yelp data, were not included. Read on to see if your favorite spot made the list.

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Olde Heritage Tavern

1 / 30

#30. Olde Heritage Tavern

- Rating: 3.6/5 (238 reviews)
- Price level: $$
- Address: 12 Housatonic St. Lenox, Massachusetts
- Categories: Sports Bars, American, Sandwiches
- Read more on Yelp

Highland Restaurant

2 / 30

#29. Highland Restaurant

- Rating: 3.7/5 (54 reviews)
- Price level: $$
- Address: 100 Fenn St. Pittsfield, Massachusetts
- Categories: Italian
- Read more on Yelp

The Roasted Garlic

3 / 30

#28. The Roasted Garlic

- Rating: 3.7/5 (215 reviews)
- Price level: $$
- Address: 483 West Housatonic St. Pittsfield, Massachusetts
- Categories: American, Sports Bars, Pizza
- Read more on Yelp

Krispy Cones Soft Serve Ice Cream

4 / 30

#27. Krispy Cones Soft Serve Ice Cream

- Rating: 3.8/5 (33 reviews)
- Price level: $
- Address: 585 South Main St. Lanesboro, Massachusetts
- Categories: Ice Cream & Frozen Yogurt, Food Stands
- Read more on Yelp

110 Grill

5 / 30

#26. 110 Grill

- Rating: 3.8/5 (48 reviews)
- Address: 489 Pittsfield Road Lenox, Massachusetts
- Categories: Gluten-Free, New American, Cocktail Bars
- Read more on Yelp

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Zucchini's Restaurant

6 / 30

#25. Zucchini's Restaurant

- Rating: 3.8/5 (114 reviews)
- Price level: $$
- Address: 1331 North St. Pittsfield, Massachusetts
- Categories: Italian, Venues & Event Spaces, American
- Read more on Yelp

Mazzeo's Ristorante

7 / 30

#24. Mazzeo's Ristorante

- Rating: 3.8/5 (263 reviews)
- Price level: $$
- Address: 1015 South St. Pittsfield, Massachusetts
- Categories: Italian, Gluten-Free, Bars
- Read more on Yelp

Frankie's Ristorante Italiano

8 / 30

#23. Frankie's Ristorante Italiano

- Rating: 3.8/5 (207 reviews)
- Price level: $$
- Address: 80 Main St. Lenox, Massachusetts
- Categories: Italian, Wine Bars
- Read more on Yelp

East Side Cafe

9 / 30

#22. East Side Cafe

- Rating: 3.9/5 (43 reviews)
- Price level: $
- Address: 378 Newell St. Pittsfield, Massachusetts
- Categories: Italian, Pizza
- Read more on Yelp

Lenox Coffee

10 / 30

#21. Lenox Coffee

- Rating: 3.9/5 (99 reviews)
- Price level: $
- Address: 52 Main St. Lenox, Massachusetts
- Categories: Coffee & Tea, Cafes
- Read more on Yelp

Mint - Indian Lakeside Dining

11 / 30

#20. Mint - Indian Lakeside Dining

- Rating: 4.0/5 (224 reviews)
- Price level: $$
- Address: 435 Laurel St. Lee, Massachusetts
- Categories: Indian
- Read more on Yelp

On A Roll Cafe

12 / 30

#19. On A Roll Cafe

- Rating: 4.0/5 (148 reviews)
- Price level: $$
- Address: 55 Pittsfield Road Lenox, Massachusetts
- Categories: Cafes, Breakfast & Brunch
- Read more on Yelp

Antimony Brewing

13 / 30

#18. Antimony Brewing

- Rating: 4.0/5 (117 reviews)
- Price level: $$
- Address: 55 Pittsfield Road Lenox, Massachusetts
- Categories: Bars, Burgers, Tapas/Small Plates
- Read more on Yelp

Brooklyn's Best

14 / 30

#17. Brooklyn's Best

- Rating: 4.2/5 (43 reviews)
- Price level: $$
- Address: 123 North St. Unit A Pittsfield, Massachusetts
- Categories: Pizza, Italian
- Read more on Yelp

Bagel And Brew

15 / 30

#16. Bagel And Brew

- Rating: 4.2/5 (78 reviews)
- Price level: $
- Address: 18 Franklin St. Lenox, Massachusetts
- Categories: Breakfast & Brunch, Bagels
- Read more on Yelp

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BLUEBiRD

16 / 30

#15. BLUEBiRD

- Rating: 4.2/5 (29 reviews)
- Address: 137 Brodie Mountain Road Hancock, Massachusetts
- Categories: Bars, Tacos, Burgers
- Read more on Yelp

Amici Berkshires

17 / 30

#14. Amici Berkshires

- Rating: 4.2/5 (86 reviews)
- Price level: $$
- Address: 5 Albany Road West Stockbridge, Massachusetts
- Categories: Italian, Cafes, Lounges
- Read more on Yelp

Electra's Cafe

18 / 30

#13. Electra's Cafe

- Rating: 4.2/5 (107 reviews)
- Price level: $$
- Address: 439 Pittsfield Road Lenox, Massachusetts
- Categories: Greek, American
- Read more on Yelp

Flo's Diner

19 / 30

#12. Flo's Diner

- Rating: 4.2/5 (45 reviews)
- Price level: $
- Address: 1245 West Housatonic St. Pittsfield, Massachusetts
- Categories: American, Breakfast & Brunch, Vegetarian
- Read more on Yelp

Haven Cafe & Bakery

20 / 30

#11. Haven Cafe & Bakery

- Rating: 4.3/5 (379 reviews)
- Price level: $$
- Address: 8 Franklin St. Lenox, Massachusetts
- Categories: Bakeries, Cafes
- Read more on Yelp

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Cello

21 / 30

#10. Cello

- Rating: 4.3/5 (21 reviews)
- Address: 37 Church St. Lenox, Massachusetts
- Categories: New American, Tapas/Small Plates, Cocktail Bars
- Read more on Yelp

The Marketplace Café

22 / 30

#9. The Marketplace Café

- Rating: 4.3/5 (225 reviews)
- Price level: $$
- Address: 53 North St. Pittsfield, Massachusetts
- Categories: Sandwiches, Coffee & Tea, Cafes
- Read more on Yelp

Boema

23 / 30

#8. Boema

- Rating: 4.4/5 (83 reviews)
- Address: 84 Main St. Lenox, Massachusetts
- Categories: Pizza
- Read more on Yelp

Six Depot Roastery and Cafe

24 / 30

#7. Six Depot Roastery and Cafe

- Rating: 4.4/5 (265 reviews)
- Price level: $$
- Address: 6 Depot St. West Stockbridge, Massachusetts
- Categories: Cafes, Coffee Roasteries
- Read more on Yelp

Brava

25 / 30

#6. Brava

- Rating: 4.4/5 (311 reviews)
- Price level: $$
- Address: 65 Church St. Lenox, Massachusetts
- Categories: Bars, Italian, Tapas/Small Plates
- Read more on Yelp

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Alta Restaurant & Wine Bar

26 / 30

#5. Alta Restaurant & Wine Bar

- Rating: 4.4/5 (418 reviews)
- Price level: $$$
- Address: 34 Church St. Lenox, Massachusetts
- Categories: New American, Wine Bars, Breakfast & Brunch
- Read more on Yelp

Drifters Bar & Restaurant

27 / 30

#4. Drifters Bar & Restaurant

- Rating: 4.5/5 (21 reviews)
- Address: 101 Dan Fox Drive bousquetmountain Pittsfield, Massachusetts
- Categories: Pubs, American
- Read more on Yelp

CRUST

28 / 30

#3. CRUST

- Rating: 4.5/5 (78 reviews)
- Price level: $$
- Address: 505 East St. Pittsfield, Massachusetts
- Categories: Pizza, Italian, Salad
- Read more on Yelp

Sibaritas

29 / 30

#2. Sibaritas

- Rating: 4.6/5 (144 reviews)
- Address: 27 McKay St. Pittsfield, Massachusetts
- Categories: Italian
- Read more on Yelp

Oasis Bar and Grill

30 / 30

#1. Oasis Bar and Grill

- Rating: 4.7/5 (21 reviews)
- Address: 615 Laurel St. Lee, Massachusetts
- Categories: American, Music Venues
- Read more on Yelp

This story features data reporting by Wade Zhou, writing by Jill Jaracz, and is part of a series utilizing data automation across 327 metros.