Highest-rated ice cream shops in Pittsfield by diners Stacker #4. 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 #3. Ayelada - Rating: 4.4/5 (82 reviews)- Price level: $- Address: 505 East St. Pittsfield, Massachusetts - Categories: Ice Cream & Frozen Yogurt- Read more on Yelp #2. Chocolate Springs Cafe - Rating: 4.6/5 (139 reviews)- Price level: $$- Address: 55 Pittsfield Road Lenox, Massachusetts - Categories: Coffee & Tea, Ice Cream & Frozen Yogurt, Chocolatiers & Shops- Read more on Yelp #1. Local-Lee Scooped - Rating: 4.7/5 (34 reviews)- Price level: $- Address: 395 Laurel St. Lee, Massachusetts - Categories: Ice Cream & Frozen Yogurt- Read more on Yelp Markus Photo and Video // Shutterstock