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 11-20 of 446
3.6 Miles
80% 5 votes
Forests 1041 Cascade Street, Pittsfield, MA 01201 MoreLess Info
A large protected forest area, Pittsfield State Forest features 65 acres of azalea fields, 30 miles of trails for hiking and biking, and an array of striking natural sights, including waterfalls and streams.
3.0 Miles
89% 38 votes
Specialty Shops 1020 South Street, Pittsfield, MA MoreLess Info
Located in Pittsfield, Massachusetts, Guido's Marketplace is the place to get fresh produce, warm baked goods and delectable ready-made foods. It is particularly renowned for its soup selection, which changes daily.
0.5 Miles
83% 184 votes
Specialty Museums 39 South St (Rte 7), Pittsfield, MA 01201 MoreLess Info
Dedicated to the rich and fascinating cultural history of the Berkshire Mountain region, the Berkshire Museum offers a diverse collection of media, art and other exhibits that make this beautiful area come alive.
1.4 Miles
84% 37 votes
Nature & Wildlife Areas Holmes Rd., Pittsfield, MA MoreLess Info
Spend the day admiring the great outdoors at the Canoe Meadows Wildlife Sanctuary in Pittsfield, Massachusetts. Managed by the Audubon Society, Canoe Meadows offers several trails and is open throughout the year.
0.9 Miles
100% 4 votes
Baseball Fields 105 Wahconah Street, Pittsfield, MA 01201 MoreLess Info
Wahconah Park features the best minor league baseball games and snacks at affordable prices. Guests enjoy clean facilities and great views of the field and players, making this an ideal day out with the family.
5.3 Miles
100% 1 votes
16

Local

Art Gallery 55 Pittsfield Rd, Ste 4A, Lenox, MA 1240 MoreLess Info
Local, a hub of artists making beautiful handmade creations, invites guests to come check out the action, work, and finished products. Items include small felt dolls, hand crafted dinnerware, paintings, textiles, and more.
5.5 Miles
96% 126 votes
Nature & Wildlife Areas 472 W Mountain Rd, Lenox, MA 01240 MoreLess Info
Located along the slopes of Lenox Mountains, Pleasant Valley Sanctuary comprises of many acres of forest, wetlands, meadows and brooks with numerous walking and hiking trails which weave through the sanctuary's hummingbird garden, hemlock gorge and much more.
5.5 Miles
91% 44 votes
Parks Route 7 and 20, Pittsfield Road, Lenox, MA 1240 MoreLess Info
Kennedy Park is a park known for its multiple hiking and mountain biking trails of various difficulty levels. Attractions include hiking, mountain biking, horseback riding, picnicking, and cross country skiing.
5.7 Miles
80% 5 votes
Horseback Riding 293 Main Street, Lenox, MA 01240 MoreLess Info
With trails going through the surrounding hills and mountains, Aspinwall Equestrian Center lead horseback rides for riders of all skill levels. Before the trip, the visitors can learn the basics of horseback riding from experienced instructors.
5.7 Miles
100% 7 votes
Nature & Wildlife Areas 472 W Mountain Road, Lenox, MA 01240 MoreLess Info
Featuring over 1,000 acres of protected land, the Mass Audubon Pleasant Valley Wildlife Sanctuary is a preserve popular among nature lovers. Visitors commonly enjoy hiking through the sanctuary, viewing the native plants and wildlife that call the location home.
Showing 11-20 of 446
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