1. Take a hike on the Appalachian Trail, which criss-crosses the county from Vermont to Connecticut. A few favorites for younger hikers are the Hinsdale branch with it’s obstacle course like stretch of rustic boardwalks and bridges, the two mile hike to Ice Gulch, where snow remains well into July or August, and the Upper Goose Pond trail, where six-bunk Upper Goose Pond cabin, complete with outhouse, porch, and tent platforms. (FREE)
2.Enjoy a house tour of the restored home of famed Moby Dick author Herman Melville (Admission Fee) or opt for a self-guided tour of the grounds (Free) at Arrowhead, Pittsfield.
3. Follow the well-maintained half-mile trail to the ruins of the “Marble Palace,” the Georgian-style mansion destroyed by fire in 1952, whose Doric columns still stand surrounded by the majestic Ashintully Gardens, Tyringham — the 30 year labor of love of music composer John McLennan. (FREE)
4. Discover the story of the Col. John Ashley’s family and the African Americans enslaved on their property during the 18th Century at the Ashley House, Sheffield. (Kids are FREE.)
5.Take in the unbeatable views of the south side of Ashmere Lake and experience an up-close opportunity to explore a modern working dam or to fish for bass from an idyllic perch fifteen feet above the dam’s rocky shoreline at the Ashmere Lake Dam, Hinsdale/Peru. (FREE)
6. The Ashuwillticook Rail Trail, Lanesboro, Cheshire, Adams is the perfect place for pushing a stroller, for toddlers pushing doll strollers, and bikers, scooter-riders or roller-bladers young and old. (FREE)
7. Take a short hike to Balance Rock State Park, Lanesborough, a 165-ton limestone boulder, balanced impossibly on a tiny stone, covered with decades of graffiti, for endless photo op possibilities.
8. Catch a family-friendly play or musical at Barrington Stage Company, Pittsfield, the local theater company with a primary focus of bringing more young people to the theater, offering educational programs, playwright mentoring, and the “KidsAct” summer program.
9. 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.
10. Explore the rare geological formation of twin rocky knolls, rising 1,000 above the surrounding meadows at Bartholomew’s Cobble, Sheffield/Ashley Falls, and the abundant wildlife, that call it home — hawks, bald eagles, turtles and over 800 species of unique plants.
11. Grab your cameras and marvel at the stunning site that is Bash Bish Falls, South Egremont, the county’s most spectacular waterfall, the 80-foot drop if Bash Bish Brook, segmented by a giant boulder,into a crystal clear basin (said to be as deep as the waterfall is high). (FREE)
12. Take a family hike to Basin Pond, Becket, an easy hike on well maintained trails, past dramatic boulders with natural stepping stone stairs and bridges over streams and brooks. A wooden lookout above the dam ruins is the perfect place to stop for a trail-side snack. (FREE)
13. The perfect day trip for families with kids of all ages! Bring your bathing suits and pack your lunch and sand toys. Beartown Mountain (Benedict Pond), Monterey.
14. A small-town community art center, with big-time creativity and imagination, Becket Arts Center, Becket offering exhibits, performances, community events, and summer youth programs.
15. Take the kids on the Becket Quarry Walk, Becket, a spectacular self-guided outdoor quarry museum and nature preserve, marked by dozens of stone pillars highlighting the history of this long abandoned quarry, including industrial-sized turn of the Century drills, winches, derricks, and mining vehicles. (FREE)
16. Pack a picnic and go play at the Becket Town Playground, Becket. (FREE)
17. Explore 26 display areas, including perennial borders, mixed borders of thousands of annuals, a rock garden, rose garden, pond garden, children’s garden and and more at the Berkshire Botanical Gardens, Stockbridge. (Kids under 12 FREE)
18. 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.
19. Take a field trip to Berkshire Fish Hatchery, New Marlborough to learn about watersheds, ecosystems, and the conservation of our county and nation’s fishery resources. (FREE)
20. 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.
21. You will have to tear your kids away from the Spark Creativity Lab if you want to see all the at Berkshire Museum, Pittsfield — the Hall of Innovation (with kid-friendly craft area), aquarium, theater, rotating exhibits, and natural history and art installations. (Kids under 3 FREE)
22. Climb aboard the Berkshire Scenic Railway Museum, Lenox, a museum dedicated to the history of railroading in the Berkshire Hills.
23. Attend a Berkshire Theatre Group camp or a family-friendly performance at the Berkshire Theatre Festival, Stockbridge.
24. Learn about a piece of local history at Bidwell House, Monterey, a 1750’s parsonage, authentically restored to tell the story of the earliest Berkshire settlers. (Kids under 6 FREE.)
25. Enjoy a game or devour some take-out from Ye Olde Forge (just up the road on Route 7) at Bill Laston Memorial Park, Lanesborough. (FREE)
26. Head to Bousquet Mountain, Pittsfield for a day of adventure year round — 200 acres of downhill skiing on the Yukon Ridge. 2 terrain parks, 23 trails, 3 double lifts, 2 carpet lifts, water slides, play a round of disc golf or explore the Adventure Park.
27. Grab your fishing pole and head to Buckley Dunton Lake, Becket, this reservoir on the southeast corner of October Mountain was created when a portion of forest area was flooded. (Rumor has it that the bass can be found hiding among the drowned tree stumps.) (FREE)
28. Schedule a day of winter fun at Butternut Ski Area, Great Barrington, featuring 22 downhill ski trails on 110 skiable acres, 11 lifts, two terrain parks, an 8-lane Tubing Center, and a full-service ski and snowboard shop.
29. Hike the trails, take in a free program or tour the gardens at Canoe Meadows, Pittsfield, located along the banks of the Housatonic River, Holmes Road, Pittsfield. (FREE; donations accepted.)
30. Spend a winter day cross country skiing, snow shoeing and skating (rentals available) at Canterbury Farm, Becket.
31. Kayak, fish, swim and enjoy the play area at Card Pond & West Stockbridge Town Hall, West Stockbridge. A play structure, skateboard park, tennis, soccer, and basketball court can also be found behind the Town Hall (21 State Line Road). (FREE)
32. Take an easy hike along the Cascades Trail, North Adams, and be rewarded with a stunning view of the 40-foot waterfall at the end of the trail. (FREE)
33. Dive into a treasure trove of history and art at Chesterwood, Stockbridge the former home of Lincoln Memorial sculptor Daniel Chester French. Tour French’s former studio and let the kids explore the sculpture garden. (Children under 13 FREE.)
34. 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 snow shoeing). (Children Under 18 FREE admission to museum; trails FREE.)
35. Enjoy the views from atop Cheshire Cobble Trail, Cheshire, a 1.2 mile (mostly uphill) round-trip hike to the Cobbles (boulders made of white Cheshire quartzite). Note: Be sure to keep young kids well back from the edge. (FREE)
36. Catch an outdoor family flick at Clapp Park, Pittsfield, one of the largest play structures in the county, playing fields, running/walking track (8 laps = 5 miles), and a spectacularly steep sledding hill. Check out Clapp Park’s Summer 2015 Outdoor Movie Schedule HERE. (FREE)
37. Purchase a ticket to a family-friendly production at The Colonial Theatre, Pittsfield. The architectural elegance of this theater alone, is worth the price of a ticket.
38. Discover the secrets of paper making at the oldest paper company in the country, at the Crane Museum of Papermaking, Dalton. Explore Crane’s Old Stone Mill and Vat House and learn how the paper for the United State’s currency is made. (FREE)
39. When school’s out, stop by the two giant play areas at Craneville Elementary School on Park Ave. — kids give them two thumbs up. (FREE)
40. Play on the climbing dinosaur and springy tractor at Greenridge Park on South Street, Dalton or enjoy a game of basketball on the full length court. (FREE)
41. Explore the ponds, apple groves and hiking trails at the Dorothy Frances Rice Forestry Preserve, Peru and make a wish in the rustic wishing well. (FREE)
42. Walk the 1.5 miles of trails — through forest, thickets, vernal pools, and wetlands —at Dry Hill, New Marlborough. And don’t miss the low bush wild blueberries free for the taking during blueberry season. (FREE; donations accepted.)
43. 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.)
44. Schedule a playdate and picnic at the newly renovated First Street Common, Pittsfield, equipped with a pavilion, bathrooms, basketball court, gazebo, new play structure, and a splash park (coming this summer) in an urban downtown setting. (FREE)
45. Hike the trails at Fountain Pond State Park (Berkshire South), Great Barrington, featuring bridges and boardwalks to keep your feet dry in the wet areas. (FREE)
46. 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.)
47. Climb upon the modern play structures at Giggle Park, Great Barrington, that give this playground an almost sculptural feel. Giggles guaranteed! (FREE)
48. Fish, hike or boat in and around Goose Pond Reservation, Lee/Tyringham. (FREE)
49. Explore the dam at Greenwater Pond, Becket. (FREE)
50. Stop by the Old Trinity Church, now known as the Guthrie Center, Great Barrington, to see where Alice’s Restaurant came into being.
51. Head into the Village of Housatonic for a bite to eat at Pleasant and Main or the Housie Market Café, and check out the playground behind the Housatonic Community Center (corner of Pleasant and Front St). (FREE)
52. Spend a day exploring Hancock Shaker Village, Pittsfield, a 750-acre living-history museum, that boasts twenty historically authentic buildings, heirloom gardens, livestock barn and pastures, and 1-mile Farm & Forest Trail. In the Discovery Room, kids can learn about farming, dress like a Shaker, make a craft to bring home, and even try their hand at milking a cow (replica). (Children 12 and under FREE.)
53. Take a ride at Harmony Trails, Dalton, this family-friendly 100-acre of property features forests and rollings meadow, offering a variety of terrains for both beginners and expert equestrians.
54. Tour the old Boston and Maine Railroad yard at Heritage State Park (Western Gateway), North Adams and discover the haunting secrets behind the famed 4.75-mile long tunnel through Hoosac Mountain, where 200 men lost their lives during the construction. (FREE)
55. Enjoy a free hay ride and apple picking in season at the Hilltop Orchards/Furnace Brook Winery, Richmond. Hikers, cross-country skiers, and snow shoers welcome to explore the full 200-acre property on the professionally designed Johnny Mash I & II Trails.
56. Take the younger kids to the Hinsdale Town Park & Kittredge Elementary Playgrounds, Hinsdale — two fantastic playgrounds. The former is perfect for smaller kids, but when school’s out, they will likely be lured across the crosswalk to the school play structure, complete “big kid” swings and slides, four square, hop scotch, and a rock climbing wall. One side of the parking lot is a car free zone, so bring your helmets and bicycles. (FREE)
57.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)
58. Volunteer with your eco-conscious kids at the Housatonic RiverWalk, Great Barrington Earth Day cleanup. (FREE)
59. Celebrate fall and get your pumpkin for carving at Howden Farm, Sheffield.
60. Spend some time skipping stones along the stream at Interlaken Park, West Stockbridge, featuring old school playground equipment, an oversized sandbox, and a gravel beach and stonewall. (FREE)
61. 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.
62. Catch a free Inside/Out performance, every Wednesday through Saturday at 6:15 p.m. during the summer at Jacobs Pillow, Becket where you are welcome to grab a seat or bring a chair or picnic blanket from home (food and drink are welcome in the performance area). (FREE)
63. Hike the mountain rails, take a scenic chairlift ride, hop all day on the bounce house and Euro bungy 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.
64. Hike the 2-mile Jug End Trail Loop (blue triangle trail markers) at the Jug End State Reservation, Egremont/Mount Washington.It will probably take you an hour or two. (FREE)
65. Bike, hike, cross-country ski and more at Kennedy Park, Lenox, with over 14 miles of groomed, town-maintained trails. (FREE)
66.Take the Jacob’s Ladder Scenic Byway/Rt 20 (the Country’s first auto road over a mountain range, completed in 1910) to the Keystone Arch Bridges, Becket/Chester/Middlefield, built for the railroad in 1833 and 1841, and the oldest bridges of their kind in the U.S. (FREE)
67. Stop for a fresh snack (pick your own blueberries or raspberries) at Kirchner’s Farm, Pittsfield.
68. Enjoy a round of disc golf at Kirvin Park (Sackett Brook), Pittsfield, surrounded by plenty of running room on soccer fields, swings and a fun play structure. (FREE)
69. Picnic at Lake Buel, Monterey/New Marlborough, a 2-mile long spring fed lake is home to Camp Half Moon and Kutsher’s Sports Academy. (FREE)
70. Sunbathe at the town beach or bring a canoe or kayak to the public boat launch, and enjoy a day of fun at Lake Garfield, Monterey, (FREE)
71. Partake in a day of swimming and sandcastle-building at Lake Mansfield, Great Barrington, a 29-acre lake surrounded by the 29-acre Lake Mansfield Forest. There’s also an old fashion jungle gym and plenty of hiking trails to enjoy. (FREE)
72. Pick your own apples, cherries, peaches, pears, plums, apricots, raspberries and blueberries Lakeview Orchards, Lanesborough.
73. Monkey around the play structures at Lanesborough Elementary Playground, Lanesborough, one fenced in and toddler friendly and one that will appeal to kids of all ages (also boasts a full-length basketball court, soccer fields, paved walk ways for young bike riders, a picnic pavilion and even porta potties in the summer). (FREE)
74. Climb to the fire tower and enjoy the panoramic views at Laura’s Lookout or venture on to Ice Glen, Stockbridge, a glacial ravine that holds ice until mid-summer (1-mile round trip). (FREE)
75. Enjoy a day at the beach at Laurel Lake, Lee/Lenox, don’t forget your fishing poles. (FREE)
76. Bike, skateboard, and rollerblade the rails at the skate park at Lee Athletic Field, Lee. (FREE)
77. Play a pick up game of soccer, football, baseball, or basketball at Lee High School, Lee (features tennis, softball, baseball, soccer and football fields). (FREE)
78. Hone little one’s biking skills on the paved beautifully landscaped walkway at Lee Elementary School, Lee, making a stop at the playground where there are three state of the art play areas for kids of all ages (behind the school). (FREE)
79. 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)
80. See a full-scale production, take in a concert or screen a movie at the historic Mahaiwe Performing Arts Center, Great Barrington.
81. 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)
82. Pack a picnic and your sand toys for a day of sandy beach fun at the swimming pond at Margaret Lindley Park, Williamstown. (FREE)
87. Take a family hike to the top of McLennan Reservation, Tyringham where you will be rewarded with sweeping views of Hale Pond and 600 acres of unspoiled forest and wetlands. (FREE)
88. Learn about Rev. John Sergeant, the first missionary to the Mohican Indians, at Mission House, Stockbridge, Sergeant’s unassuming little Colonial house built in 1742 that showcases a remarkable collection of early American furniture and art and home to a small Native American Museum. (Kids FREE.)
89. Venture along one of the county’s most well-traveled hiking trails to the Squaw Peak summit of Monument Mountain, Great Barrington, with sweeping views stretching from the Catkills to Mt. Greylock. (FREE)
90. 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)
91. Take in music on the terrace, tour the main house and out buildings, 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.)
92. Mark your calendar for the annual Cummington Fair at the Cummington Fairgrounds on Fairgrounds Road, Cummington featuring carnival rides, agriculture exhibits, animal judging and more.
93. Drive to the summit of Mount Greylock and take in a program and grab a bite to eat at Bascom Lodge, Adams. Check out the DCR’s list of suggested day hikes on the mountain. (FREE; fees for food and some programs.)
94. 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)
95. Visit the farm stand at Mountain View Farm, Lanesborough, and purchase fresh veggies by the bushel or pick your own blueberries and strawberries.
96. Play on the swings or relax on the shaded benches at Muddy Brook Elementary School, Great Barrington after a long hike at Monument Mountain, or explore the nearby pond with your budding scientists. (FREE)
97. Learn about the history of movie animation and the Berkshire’s role in it, create your own stop-action film and browse the gift shop at the Museum of Animagic, Lee. (FREE)
98. Become an astronaut, train conductor, and/or soldier at the Museum of History and Science, North Adams, or learn about bugs and creatures and other kid favorites, at this Berkshire hidden treasure. (FREE)
99. Explore the grounds of the 350-acre property overlooking the village of Stockbridge at the National Shrine of Divine Mercy, Stockbridge where you will find the Lourdes Candle Grotto, the Holy Family Shrine, the groves of St. Therese and St. Francis, the Mother of Mercy Outdoor Shrine, and the Shrine of the Holy Innocents, divine destinations for thousands of religious pilgrims each year. (FREE)
100. Participate in a scavenger hunt, follow trails past 550 million year old marble bridges and arches, and traverse a series of stone stairs and metal gangways over incredible water falls, caverns, and gorges at Natural Bridge State Park, North Adams.
101. Step back in time and experience life in the Gilded Age at Naumkeag, Stockbridge. Explore the 44-room Choate family “cottage” and Naumkeag gardens, including the famed Blue Steps, Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden, and Chinese Garden. (Kids up to 12 FREE.)
102. Take in a Steeplecats game at Noel Field Athletic Complex, North Adams (the complex also boasts a basketball court, soccer field, walking trails, track, and playground). (FEE for games; parks, trails, etc. are FREE.)
103. Participate in art-making activities, browse the kid-friendly exhibits or sign up for a workshop, at the Norman Rockwell Museum, Stockbridge. The grounds are great for exploring, too. (FREE for kids 5 and under.)
104. Star gaze with Arunah Hill Natural and Science Center ; hike the trails; take in a program in warmer weather months or cross-country ski in the winter at Notchview Reservation, Windsor, with 3,000 acres of wooded passages, historic hayfields and pastures, stone walls and cellar holes will have you coming back to hike and explore year round. (Most programs are FREE; admission is FREE for kids 12 and under.)
105. Swim, boat, camp or hike along North Pond, Florida, nestled in the Savoy Mountain State Forest, the vistas at the top of some of this state park’s trails are amazing.
106. Pitch a tent for a night or two; and explore the 16,500 acres of winding woodland trails that circle past lakes, reservoirs, marshlands, and geological formations at October Mountain State Forest, Becket/Lee/Lenox.
107. Explore beautifully constructed bridges and hedged with cool sites, like the old dam, an abandoned vintage auto, old mill ruins, jutting boulders, a weather-protected trail journal, and a stone stairway along the Old Mill Trail, Hinsdale. (FREE)
108. 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 their may be a geocache site here, too. (FREE)
109. Attend an outdoor concert during the “Live on the Lake” summer music series at Onota Lake/Burbank Park, Pittsfield. “Live on the Lake” Schedule for Summer 2016 coming soon. (FREE)
110. Kayak, jet ski, swim, picnic and/or just relax at Otis Reservoir/Tolland State Forest, Otis.
111. Spend a day skiing at Otis Ridge, Otis — it may be the smallest ski area in the Berkshires but it’s big on family fun, with 10 trails, kids programs, lessons and ski camps.
112. Monkey around at Pinegrove Park, Dalton, and pack a snack to enjoy afterwards in the pavilion while watching a football, softball, baseball or basketball league (all depends on the season) on the grounds. (FREE)
113. Explore over 30 miles of Taconic Mountain Range trails or fish at 2,150-feet above sea level, in Berry Pond, one of the highest bodies of water in Massachusetts at the Pittsfield State Forest, Pittsfield. Swimming and picnicking is also available in the natural cold spring pool at LuLu Brook.
114. Experience a different adventure and spot new wildlife, enjoy a family fun or enroll in a nature camp or family program at Pleasant Valley Wildlife Sanctuary, Lenox. (Lenox residents are FREE.)
115. Pack your swim suits and fishing poles for a relaxing day of family fun at Plunkett Reservoir, Hinsdale, a 73-acre reservoir with a public boat launch and sandy beach.
116. Rent a boat for the day at Pontoosuc Lake, Pittsfield/Lanesborough and spend the day tubing or waterskiing in this beautiful 480-acre lake.
117. Follow an old wooded road, mowed meadow passages and forested footpaths past cellar holes, stone walls and the remnants of a long abandoned Colonial settlement of Leffingwell, where the first Colonial settlers of New Marlborough were born at Questing, New Marlborough. (FREE)
118. View the five distinct falls, including a horsetail, slide, fan, plunge and 100-foot cascade at Race Brook Falls, Sheffield and take in the expansive view of Massachusetts, New York, and Connecticut at the summit Mount Everett. (FREE)
119. Experience a high flying adventure with kids ages 7 and up (must be 55-inches or taller) at Ramblewild Adventure Park, Lanesborough, the environmentally-friendly, 900-acre adventure park that features eight distinct 15 – 17 element aerial obstacle courses, where action junkies can test challenge their skill (a will) on high wires, zip lines, balancing logs, rope ladders, cargo nets, suspended bridges and 129 more ways of getting from tree to tree.
120. Skate, play or catch a youth ball game at Renfrew Park, Adams, that features basketball courts, a super fun play structure, a skate park, and a killer snack bar when games are being played. (FREE; food for a fee)
121. Pick your own apples Macintosh, Honey Crisp, Cortland, Gala, Empire, Macoun, Spencer, Liberty, Ida Red, Fugi, Braeburn) at Riiska Brook Orchard, Sandisfield.
122. Get your hike on at Savoy Mountain State Forest, Florida featuring over 50 miles of wooded hiking trails, as well as North Pond (sandy beach with restrooms), South Pond (year round camp and cabin rentals available), Bog Pond (floating bog islands!!), and Tannery Falls (a series of smaller waterfalls feeding into a dramatic 50-foot cascade).
123. Catch an outdoor kid-friendly theater performance at the Shakespeare & Company, Lenox Rose-Footprint Theater.
124. Take in an educational children’s and family program at Sheep Hill, Williamstown, a truly unique setting (a 50-acre former dairy farm).
125. 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.
126. Catch an outdoor summer concert at Springside Park, Pittsfield or attend a gardening workshop or demo offered on select Saturday mornings and before “Tuesday Night in the Park” music series. (Most events are FREE.)
127. 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)
128. Take a picnic to the Stockbridge Bowl Boat Launch, Stockbridge, there is a lovely picnic area adjacent to the public access boat launch on Rt 183, a great place to stop after a hike at Steven’s Glen or a visit to the Shark Rock or Interlaken Park playground. Note: While the boat launch area is open to the public, a town resident sticker is required at Stockbridge Town Beach (but only during the summer season). (FREE)
129. Play old school-style at Stockbridge Town Playground, Stockbridge featuring multiple play structures, swings, and old school jungle gym, merry-go-round and spring-loaded riding toys, as well as the town little league field and tennis courts.
130. Visit the Sunny Banks Ranch, Becket, for a private lesson or a full day of team roping and ranch sorting. Mosey on by for a trail ride or just drop in and watch the action.
131. Visit the birthplace of pioneering suffragist and abolitionist, Susan B. Anthony, and discover the regional influences that shaped her life. The Susan B. Anthony Birthplace Museum, Adams family-friendly and kid-approved. (Kids 6 and under are FREE)
132. Experience some fall fun at Taft Farms, Great Barrington, pesticide free family farm, featuring hay rides, a corn maze, a pick your own pumpkin patch and more.
133. Learn about local land conservation at Tamarack Hollow, Windsor, highland valley nature and cultural center with a 32-acre conservation area and a unique and ecologically sensitive forest ecosystem.
134. 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)
135. Walk through mountain meadows and follow the Loop Trail past ancient bedrock formations to the summit for panoramic views of the Tyringham Valley at Tyringham Cobble, Tyringham. Challenge little hikers to find “Rabbit Rock” and to create names for other unusually shapes rock formations.
136. Schedule a visit to Tyringham Park, Tyringham, a gated play wonderland for parents and kids, with a giant play structure and multiple swinging and sliding options. (FREE)
137. Find the secret (well almost) swimming hole beside a peaceful waterfall, located in a 5-acre park complete with walking trails and sunning rocks at Umpachene Falls, New Marlborough. (FREE)
138. Take a relaxing trail ride or ride in the arenas at Undermountain Farm, Lenox.
139. Explore the Upper Housatonic Valley African American Heritage Trail, South Berkshires, a mapping of 48 sites, throughout 29 Massachusetts and Connecticut towns, celebrating local African Americans who played roles in shaping our nation’s history. (FREE)
140. 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).
141. Attend the John Keator Memorial Pumpkin Walk, at the Washington Town Park, Washington, complete with a state of the art Jack o’lantern display, bonfire, hayrides and trick-or-treat!
142. Dip your toes in the frigid waters at the bottom of the spectacular 40-food cascade at Wahconah Falls State Park, Dalton/Windsor. The nearby 1/2-mile Loop Trail is an easy trek that will take you to the top of the falls and through the shade of the surrounding conifer forest. (FREE)
143. Attend a Pittsfield Suns ballgame or a free summer concert at Wahconah Park, Pittsfield, one of the country’s only remaining ballparks with a wooden grandstand.
144. Learn about the early life and Great Barrington public school education of the Civil Rights leader, prolific author and recipient of Harvard’s first African American Doctoral graduate, W.E.B. Du Bois at the W.E.B. Du Bois Center, Great Barrington, and explore the African American experience and issues regarding social justice. (FREE)
145. Visit Whitney Farms, Cheshire and check out the peacocks, feed sheep, goats and pony and visit pumpkin patch (seasonal).
146. 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 Proessor of astronomy from 1901 – 1942, Willis Milham).
147. 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)
148. Listen to music on the beach at Windsor Lake Park, North Adams during the Free Summer concert series, Concerts on the Lake. (FREE)
149. Stop in at Windy Hill Farm, Great Barrington for some fresh pressed cider or visit the holiday shop for fresh-cut winter greens.
150. At 2,240-feet, Whitcomb Summit, Florida is the highest elevation on the Mohawk Trail and with visibility as far as Vermont and New Hampshire, a trip to the observation tower for the views is highly recommended.
151. Picnic, swim and just meander you day away at York Lake, Sandisfield.
152. Attend a local festival such as 3rd Thursday in Pittsfield; Downstreet Art in North Adams, Summer Sundays @ 6 in Williamstown and the Apple Squeeze in Lenox. (FREE)
153. Take a holiday stroll at one of the many holiday walks and festivities in the region — Dalton, Stockbridge, and Williamstown host a few of our favorites. (FREE)
154. Get festive at one of the regions award-winning parades such as the Lee Founders Day Parade; Fourth of July Parade in Pittsfield; and the Fall Foliage Parade in North Adams. (FREE)
155. Attend a kid-friendly concert at the Great Barrington Bandstand. (FREE)
156. Ski the trails at Catamount Ski Area and Aerial Adventure Park, South Egremont/Hillsdale, NY, and,in the off season visit the aerial Adventure park, with 12 separate courses of varying difficulty, 170 adventure elements and over 50 zip lines, including two 2,000-footers!
157. Attend the annual Kids Can Too Concert, brave the Bang on a Can six-hour Music Marathon (with plenty of breaks in between) or pop in the museum for pop-up gallery recitals at MASS MoCA, North Adams.
158. Throw on a smock and get yours hands dirty in a hand’s on workshop or studio art class at the IS183 Art School. Children and adult of all skill levels are welcome!
Just Beyond the Berkshires:
159. Climb the historic 68-foot Goshen Fire Tower in the DAR State Forest, Goshen, cool down afterward with a swim at the pristine beach or picnic at the shady picnic site and pavilions (skating and cross-country are a must in the winter months).
160. Explore the geological past of Western MA in this breathtaking canyon with 70-foot walls, carved through metamorphic bedrock over the centuries by ancient glaciers at the Chesterfield Gorge, Chesterfield. (Kids under 12 are FREE.)
161. Visit the site where Glendale Brook plunges 150 feet over rock ledges, to the middle branch of the Westfield River to create Glendale Glendale Falls, Middlefield, one of the state’s highest and most powerful waterfalls. (FREE)
162. Spend the day riding the train, playing mini golf, paddling the peddle boats, visiting the zoo, running through the spray park or exploring the many playgrounds and playing fields at Look Park in Florence. (Just $5 per car weekdays | $7 per car weekends)
163. Nestled behind Berkshire Trail Elementary School in Cummington is the Pettingill Memorial Recreational Field where kids of all ages will be drawn to the giant tower with corkscrew slide, zip line feature, springy waverunner and motorcycle rides, and acres of grassy running space.
164. Tour the home (access varies), the barn, and the 2.5 miles of surrounding trails year round William Cullen Bryant Homestead, Cummington, the home of one of America’s most celebrated poets sits atop a hill overlooking the Westfield River Valley, just a few miles east of the Berkshires. Read your kids Bryant’s famous poem “The Rivulet” and head to this National Historic Landmark to explore the landscape that inspired the poem.