Date Ideas in Pittsfield, MA

  • TripBuzz discovered 86 different types of activities for couples in the Pittsfield area, including Theaters (like Barrington Stage Company), Movie Theaters (like Beacon Cinema), Breweries (like Wandering Star Craft Brewery) and Winery/Vineyard (like Balderdash Cellars), and much more.
  • We discovered a total of 88 date ideas in or near Pittsfield, Massachusetts, including 73 fun or romantic activities in nearby cities within 25 miles like Lenox, North Adams, Williamstown and Great Barrington.
  • TripBuzz discovered 86 different types of activities for couples in the Pittsfield area, including Theaters (like Barrington Stage Company), Movie Theaters (like Beacon Cinema), Breweries (like Wandering Star Craft Brewery) and Winery/Vineyard (like Balderdash Cellars), and much more.
  • We discovered a total of 88 date ideas in or near Pittsfield, Massachusetts, including 73 fun or romantic activities in nearby cities within 25 miles like Lenox, North Adams, Williamstown and Great Barrington.
Showing 411-420 of 446
47.5 Miles
50% 2 votes
Family Fun Center 138 South Road, Enfield, CT 6082 MoreLess Info
Skater City is an indoor amusement facility that features a variety of entertainments. Attractions include roller skating, toxic laser tag, miniature golf, and an extensive video game arcade. The facility hosts birthday parties and special events.
47.6 Miles
84% 166 votes
Mountains off Rte 7A, Manchester, VT MoreLess Info
Experience Mount Equinox, southern Vermont's highest peak, via the Skyline Drive, with picnic areas and lookouts along its 5.2 mile climb. At the summit, visit the Saint Bruno Scenic Viewing Centre, with information about the Carthusian Monks, whose only US monastery is located on the mountain.
47.6 Miles
77% 52 votes
Castles Bangall Road, Millbrook, NY MoreLess Info
Guided tours of Wing Castle and its grounds are available at regular times from Memorial Day to Labor Day. There is also an on-site bed and breakfast that embraces the style and decor of a European fairy tale.
47.6 Miles
89% 18 votes
Hiking Trails Amherst, MA MoreLess Info
Passing through Amherst, Massachusetts, the Metacomet-Monadnock Trail is one of New England's most popular hiking destinations. It is one component of the New England Scenic Trail route. This trail is best hiked in late summer and early autumn.
47.8 Miles
Tours and wine tastings are offered daily at the Millbrook Vineyards & Winery throughout the year. From Memorial Day through October, guests can also visit the Vineyard Grill and Cafe to eat local gourmet food in a large tent near the pond.
47.8 Miles
96% 72 votes
Nature & Wildlife Areas 316 Old Stage Road, Saugerties, NY 12477 MoreLess Info
The Catskill Animal Sanctuary is a 110 acre animal sanctuary for farm animals rescued from animal cruelty. Attractions include a guided tour of the sanctuary, cooking classes, overnight lodging, and various special events.
47.8 Miles
94% 18 votes
Observation Decks Dover, VT MoreLess Info
The area known as the Skyline Overlook is found on a part of Hogback Mountain. On a clear day, visitors can enjoy a view of roughly 100 miles in every direction from this high point.
47.8 Miles
50% 6 votes
Movie Theaters 530 Bushy Hill Road, Simsbury, CT 06070 MoreLess Info
Showing the most recent films, Hoyts Simsbury Commons 8 has movies for all ages. Along with 3D digital projection, the theater is equipped with eight screens and concessions featuring a variety of refreshments.
47.8 Miles
100% 2 votes
Parks Hartford Rd Rt 185, Simsbury, CT 06070 MoreLess Info
The Pinchot Sycamore Tree Park leisure park that is home to the Pinchot Sycamore, which is best known for being the largest tree in Connecticut. The park has trees that are estimated to be 200-300 years old.
47.9 Miles
82% 351 votes
Resorts 400 Mountain Rd., Dover, VT MoreLess Info
Located in the Green Mountains of southern Vermont, the Mount Snow Resort is both a mountain and ski area for a variety of activities. It serves as the closest big mountain resort to most metropolitan areas in the Northeast United States.
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