- Our list of the best things to do in Pittsfield, Massachusetts, features the top 104 nearby activities — including 61 great attractions with user approval ratings of 90% or more!
- Pittsfield, MA has a variety of great sights and experiences nearby. Top categories include: Museums & Galleries, Entertainment & Shows, Outdoor Places, and Sights & Landmarks.
- The results below include the top 18 things to do within the city of Pittsfield, MA , followed by 86 popular activities in nearby cities, including Lenox, North Adams, Williamstown, Great Barrington, Lee, Charlemont, Stockbridge and Ashfield
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44.4 Miles
Tivoli Sailing Company offers a variety of chartered boat excursions, both catered and uncatered. They offer local sailing and trips as far as the Caribbean. They also offer sailing lessons for children and adults.
44.4 Miles
100%
6 votes
43 Partition street, Saugerties, NY 12477
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Providing outdoor activities for the entire family, Saugerties Village Beach & Playground is a popular park in the warmer months. Along with swimming and other beach fun, the park also allows for both kayaking and boating.
44.4 Miles
Owned and operated by Carmike Cinemas, Cinerom is a local movie theater showing the latest film releases to its guests. Amenities at the theater include theater rentals and a number of concession options.
44.4 Miles
A contemporary artist who paints in the Impressionist style, Catherine M Elliott maintains a gallery of paintings and prints. Elliott paints outdoors, and captures conditions of light and of atmosphere in her work.
44.4 Miles
Featuring a stone tower, Retreat Trails provides visitors with a scenic path in a wilderness that is home to eagles and deer. One of the highlights is an Olympic ski jump called the Harris Hill Ski Jump.
44.4 Miles
With the goal of spreading performing arts educations among the community's youth, New England Youth Theatre has classes for improv comedy, crafts, public speaking, and more. Each production hosted by the theater showcases the talent of its students.
44.4 Miles
Saugerties Marina is a family owned marina offering a variety of services. Among the services offered are motorboat and kayak rentals, transportation, docking, and boat service and repairs. The marina also maintains a full service ship store.
44.5 Miles
Chocolate lovers can all agree on one thing, Krause's Chocolates are one of the finest chocolatier's in the world. Featuring more than 44 varieties of hand-dipped chocolate, treat yourself today.
44.5 Miles
88%
91 votes
1480 Litchfield Turnpike, New Hartford, CT 06057
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Located in New Hartford, Connecticut, the Connecticut Valley Winery produces white, red and dessert wines. Tastings are available on Saturdays and Sundays. Patrons may bring a bag lunch and eat on the patio or in front of the fireplace in the main building.
44.5 Miles
Several types of cheeses are offered at The Vermont Cheese House. Visits revolve around purchasing and tasting cheeses along with a variety of wines from around the United States and specialty sweets.