
Highest-rated restaurants with outdoor seating in Pittsfield by diners
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.
#30. Olde Heritage Tavern
- Rating: 3.6/5 (238 reviews)
- Price level: $$
- Address: 12 Housatonic St. Lenox, Massachusetts
- Categories: Sports Bars, American, Sandwiches
- Read more on Yelp
#29. Highland Restaurant
- Rating: 3.7/5 (54 reviews)
- Price level: $$
- Address: 100 Fenn St. Pittsfield, Massachusetts
- Categories: Italian
- Read more on Yelp
#28. The Roasted Garlic
- Rating: 3.7/5 (215 reviews)
- Price level: $$
- Address: 483 West Housatonic St. Pittsfield, Massachusetts
- Categories: American, Sports Bars, Pizza
- Read more on Yelp
#27. Krispy Cones Soft Serve Ice Cream
- Rating: 3.8/5 (33 reviews)
- Price level: $
- Address: 585 South Main St. Lanesboro, Massachusetts
- Categories: Ice Cream & Frozen Yogurt, Food Stands
- Read more on Yelp
#26. 110 Grill
- Rating: 3.8/5 (48 reviews)
- Address: 489 Pittsfield Road Lenox, Massachusetts
- Categories: Gluten-Free, New American, Cocktail Bars
- Read more on Yelp
#25. Zucchini's Restaurant
- Rating: 3.8/5 (114 reviews)
- Price level: $$
- Address: 1331 North St. Pittsfield, Massachusetts
- Categories: Italian, Venues & Event Spaces, American
- Read more on Yelp
#24. Mazzeo's Ristorante
- Rating: 3.8/5 (263 reviews)
- Price level: $$
- Address: 1015 South St. Pittsfield, Massachusetts
- Categories: Italian, Gluten-Free, Bars
- Read more on Yelp
#23. Frankie's Ristorante Italiano
- Rating: 3.8/5 (207 reviews)
- Price level: $$
- Address: 80 Main St. Lenox, Massachusetts
- Categories: Italian, Wine Bars
- Read more on Yelp
#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
#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
#20. Mint - Indian Lakeside Dining
- Rating: 4.0/5 (224 reviews)
- Price level: $$
- Address: 435 Laurel St. Lee, Massachusetts
- Categories: Indian
- Read more on Yelp
#19. On A Roll Cafe
- Rating: 4.0/5 (148 reviews)
- Price level: $$
- Address: 55 Pittsfield Road Lenox, Massachusetts
- Categories: Cafes, Breakfast & Brunch
- Read more on Yelp
#18. Antimony Brewing
- Rating: 4.0/5 (117 reviews)
- Price level: $$
- Address: 55 Pittsfield Road Lenox, Massachusetts
- Categories: Bars, Burgers, Tapas/Small Plates
- Read more on Yelp
#17. Brooklyn's Best
- Rating: 4.2/5 (43 reviews)
- Price level: $$
- Address: 123 North St. Unit A Pittsfield, Massachusetts
- Categories: Pizza, Italian
- Read more on Yelp
#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
#15. BLUEBiRD
- Rating: 4.2/5 (29 reviews)
- Address: 137 Brodie Mountain Road Hancock, Massachusetts
- Categories: Bars, Tacos, Burgers
- Read more on Yelp
#14. Amici Berkshires
- Rating: 4.2/5 (86 reviews)
- Price level: $$
- Address: 5 Albany Road West Stockbridge, Massachusetts
- Categories: Italian, Cafes, Lounges
- Read more on Yelp
#13. Electra's Cafe
- Rating: 4.2/5 (107 reviews)
- Price level: $$
- Address: 439 Pittsfield Road Lenox, Massachusetts
- Categories: Greek, American
- Read more on Yelp
#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
#11. Haven Cafe & Bakery
- Rating: 4.3/5 (379 reviews)
- Price level: $$
- Address: 8 Franklin St. Lenox, Massachusetts
- Categories: Bakeries, Cafes
- Read more on Yelp
#10. Cello
- Rating: 4.3/5 (21 reviews)
- Address: 37 Church St. Lenox, Massachusetts
- Categories: New American, Tapas/Small Plates, Cocktail Bars
- Read more on Yelp
#9. The Marketplace Café
- Rating: 4.3/5 (225 reviews)
- Price level: $$
- Address: 53 North St. Pittsfield, Massachusetts
- Categories: Sandwiches, Coffee & Tea, Cafes
- Read more on Yelp
#8. Boema
- Rating: 4.4/5 (83 reviews)
- Address: 84 Main St. Lenox, Massachusetts
- Categories: Pizza
- Read more on Yelp
#7. Six Depot Roastery and Cafe
- Rating: 4.4/5 (265 reviews)
- Price level: $$
- Address: 6 Depot St. West Stockbridge, Massachusetts
- Categories: Cafes, Coffee Roasteries
- Read more on Yelp
#6. Brava
- Rating: 4.4/5 (311 reviews)
- Price level: $$
- Address: 65 Church St. Lenox, Massachusetts
- Categories: Bars, Italian, Tapas/Small Plates
- Read more on Yelp
#5. Alta Restaurant & Wine Bar
- Rating: 4.4/5 (418 reviews)
- Price level: $$$
- Address: 34 Church St. Lenox, Massachusetts
- Categories: New American, Wine Bars, Breakfast & Brunch
- Read more on Yelp
#4. Drifters Bar & Restaurant
- Rating: 4.5/5 (21 reviews)
- Address: 101 Dan Fox Drive bousquetmountain Pittsfield, Massachusetts
- Categories: Pubs, American
- Read more on Yelp
#3. CRUST
- Rating: 4.5/5 (78 reviews)
- Price level: $$
- Address: 505 East St. Pittsfield, Massachusetts
- Categories: Pizza, Italian, Salad
- Read more on Yelp
#2. Sibaritas
- Rating: 4.6/5 (144 reviews)
- Address: 27 McKay St. Pittsfield, Massachusetts
- Categories: Italian
- Read more on Yelp
#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.