Things to Do in Williamstown, Hancock, New Ashford โ€” Bucket List

Numbers 31-45

By Berkshires Macaroni Kid June 11, 2019
Whether looking for things do in Williamstown or New Ashford MA for kids, parents, grandparents, etc. we’ve got a list that has something fun for every member of your family.

NOTE: As the state releases new guidelines, please practice social distancing guidelines and know that we try to keep these lists as updated as possible. Many sites and venues will not be opening for the summer so please call ahead before going. If you see a change please email

Williamstown (31-43)
  • Explore the galleries or search for geocached “treasures” hidden alongside campus hiking trails at the Clark Art Institute, Williamstown (also the perfect spot for some winter sledding or snowshoeing). (Children Under 18 FREE admission to the museum; trails FREE.)
  • Head for adventure with kids big and small at Field Farm, Williamstown. Stroll along the Pond Trail complete with wood bridges and perfect for small kids; the 1 mile North Trail that will guide you past spectacular outdoor sculptures and unbeatable mountain views; and, the Caves Loop will capture young explorers imaginations as they watch the small stream disappear into a series of underground caves. (FREE; donations accepted.)
  • Take a walk, ski, and snowshoe on the trails of  Hopkins Memorial Forest, Williamstown, a 2,600-acre preserve, with over 15 miles of open to the public. (FREE)
  • Pack a picnic and your sand toys for a day of sandy beach fun at the swimming pond at Margaret Lindley Park, Williamstown. (FREE)
  • Take in an educational children's and family program at Sheep Hill, Williamstown, a truly unique setting (a 50-acre former dairy farm).
  • Hike to see snow in the summer at the Snowhole, Williamstown/New York State Line, a 50-foot chasm, where MA, NY, and VT meet in the Taconic Mountain range. There is a cave on site and a flashlight is recommended for parents to allow kids to peer inside of this geological wonder.
  • Attend a free planetarium show at Williams College Hopkins Observatory | Milhelm Planetarium, Williamstown, the oldest existing observatory in the United States and the Milhelm Planetarium is quite possibly the nation’s first planetarium (named for Professor of astronomy from 1901 - 1942, Willis Milham).
  • Watch a free family-friendly outdoor theater production at Poker Flatts Field courtesy of Williamstown Theatre Festival, Williamstown, or attend a family-friendly theater workshop. (FREE)
  • Partake in the town's annual Summer Sundays @ 6, and take in an outdoor movie to wrap up your evening of fun.
  • Walk from Massachusetts to Vermont along this beautiful scenic trail at Mountain Meadow Preserve, Williamstown/Pownal, VT, with views of Mt. Greylock and the Hoosac Valley. (FREE)
  • Attend the annual Big Splash Carnival at Sand Springs Pool or simply spend the day at the pool soaking up the rays.
  • Take a winter stroll and enjoy the festivities at the annual weekend-long Williamstown Holiday Walk Festivities.
  • Take in a college game — soccer, football, basketball, lacrosse etc. — at Williams College.
Hancock (44-45)
  • Sample the maple syrup and enjoy a short stack of pancakes during the spring season at Ioka Valley Farm, Hancock. Kids can also swing from the farm-themed play structure and cuddle up to the friendly farm animals in Uncle Don’s Barnyard during the summer months, and enjoy the cornucopia of fall-themed activities including the free tractor rides and corn maze.
  • Hike the mountain trails, take a scenic chairlift ride, hop all day on the bounce house and Euro bungee trampoline, soar on the giant swing and Soaring Eagle Zip ride, climb through the Kids Climb ropes course, explore the Ponderosa Playground in the Kids’Zone, conquer the giant climbing wall, and don’t forget the alpine slide and mountain coaster at Jiminy Peak, Hancock.