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Things to Do in Lenox, Richmond, Mount Washington —Bucket List

Numbers 142-163

By Berkshires Macaroni Kid August 1, 2019

Whether looking for things do in Lenox 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 kellym@macaronikid.com.

Lenox (142-158)
  • Saddle up with Berkshire Horseback Adventures, Lenox for a once-in-a-lifetime tour of the back trails of Lenox Mountain, at the Aspinwall Adult Equestrian Center at 293 Main Street in Lenox.
  • Climb aboard the Berkshire Scenic Railway Museum, Lenox, a museum dedicated to the history of railroading in the Berkshire Hills.
  • Bike, hike, cross-country ski and more at Kennedy Park, Lenox, with over 14 miles of groomed, town-maintained trails. (FREE)
  • Challenge your kids to a game of basketball on the full-length basketball court at the Lenox Community Center, Lenox or see who can slide down the super fast corkscrew slide the quickest (the giant crocodile is also an irresistible play structure). (FREE)
  • Hike, ski, snowshoe, run, mountain bike, hunt, fish, forage, nature watch, paint pictures, take photographs, eat and drink, walk your dog off-leash, hunt for geocaches, nap or get married at the Mahanna Cobble, Lenox/Pittsfield. (FREE)
  • Teach your kids the old driveway classic, hopscotch, at the Morris School Playgrounds, Lenox. A new play structure and the basketball courts are also tempting to family members of all ages. (FREE)
  • Take in music on the terrace, tour the main house and outbuildings, picnic in the gardens or register for an educational program at The Mount, Lenox, the historic home of Pulitzer Prize-winning author Edith Wharton. (Kids 18 and under FREE.)
  • Visit Shark Rock at Olivia’s Lookout, Richmond/Lenox and venture along the nearby hiking trails include Yukon Ridge North, Yukon Ridge South, Burbank Trail, Charcoal Trail, the Micheal H. Walsh Trail, and Steven’s Glen. We hear there may be a geocache site here, too. (FREE)
  • Experience a different adventure and spot new wildlife, enjoy a family fun program or enroll in a nature camp at Pleasant Valley Wildlife Sanctuary, Lenox. (Lenox residents are FREE.)
  • Catch an outdoor kid-friendly theater performance at the Shakespeare & Company, Lenox Rose-Footprint Theater.
  • Attend a free Friday morning rehearsal of the Berkshire Symphony Orchestra at Tanglewood, Lenox, or stop by for its Highland Street Foundation Free Fun Friday. (FREE)
  • Take a relaxing trail ride or ride in the arenas at Undermountain Farm, Lenox.
  • Step back in time at Ventfort Hall, Lenox, a 28-room Jacobean Revival-style mansion — the exterior of Ventfort Hall, grand staircase and Great Hall were staged as the St. Cloud Orphanage in “The Cider House Rules” (the 1999 Academy Award-winning film starring Tobey McGuire and Charlize Theron).
  • Attend a local festival such a Downstreet Art in North Adams, Summer Sundays @ 6 in Williamstown and the Apple Squeeze in Lenox. (FREE)
  • Take a holiday stroll at one of the many holiday walks and festivities in the region — Dalton, Stockbridge, Lenox, and Williamstown host a few of our favorites. (FREE)
  • Take a walking tour of the 46-acre estate housing the vast contemporary collection and famed abstract works of Suzy Felinghuysen and George L. K. Morris at the Frelinghuysen Morris House and Studio, Lenox. (Children under 12 FREE.)
  • Take a dip in Laurel Lake, Lenox.
Richmond (159-163)
  • Sample fresh-baked cider donuts, muffins, pies, turnovers, and an assortment of seasonal goodies at Bartlett Orchards, Richmond, or pick your own apples, raspberries, and flowers, every weekend from Labor Day to Columbus Day.
  • Ride horses at the Berkshire Equestrian Center, Richmond, located on the property of the historic Inn at Richmond, the center offers something for horse enthusiasts of all ages and abilities.
  • Enjoy a free hayride and apple picking in season at the Hilltop Orchards/Furnace Brook Winery, Richmond. Hikers, cross-country skiers, and snowshoers welcome to explore the full 200-acre property on the professionally designed Johnny Mash I & II Trails.
  • Visit Shark Rock at Olivia’s Lookout, Richmond/Lenox and venture along the nearby hiking trails include Yukon Ridge North, Yukon Ridge South, Burbank Trail, Charcoal Trail, the Micheal H. Walsh Trail, and Steven’s Glen. We hear there may be a geocache site here, too. (FREE)
  • Experience the natural stone steps, rustic benches and bridges, an observation deck, and magnificent views of gorges, glens and falls at Steven’s Glen, Richmond, 128-acre parcel of land with family-friendly hiking trails. (FREE)
Mount Washinton