City of Pittsfield Parks & Recreation cityofpittsfield . org / departments / parks _ and _ recreation
Williamstown Rural Lands ( WRL ) rurallands . org
Berkshire Family Hikes berkshirefamilyhikes . com
City of Pittsfield Parks & Recreation cityofpittsfield . org / departments / parks _ and _ recreation
Pittsfield boasts a variety of trails and recreational areas that cater to families , novice hikers , and experienced adventurers . Pittsfield Park / Open Space Program Manager James McGrath provides insights into the best trails and hiking opportunities within the Pittsfield recreation system , highlighting accessibility , family-friendly features , and hidden gems .
Cadwell Woods Conservation Area
Barker Road , Pittsfield Recently acquired by the city , Cadwell Woods is a new conservation area with a small , growing trail network . “ It ’ s about 50 acres in size , and while the trails are still being developed and signed , it ’ s a fun little property to explore ,” says McGrath . The property is adjacent to Clapp Park and the Southwest Branch of the Housatonic River , offering a scenic , 2.4-mile hike for novice hikers .
Pittsfield State Forest
Cascade Street , Pittsfield For those seeking more rugged trails , Pittsfield State Forest offers extensive hiking opportunities . “ Pittsfield State Forest is great for wilderness hiking and has a mobility-accessible trail off their main parking area ,” mentions McGrath . The forest features a variety of trails for different skill levels , making it a perfect destination for more intermediate hikers in Pittsfield . McGrath emphasizes the importance of being prepared and responsible while hiking . “ Always get yourself oriented before you get on the trails , whether with paper maps or other resources ,” he advises . “ Pack it in , pack it out — ensure that you carry out all trash to keep the trails clean . And remember , take only photographs and leave only footprints , especially with wildflowers and other sensitive plants .”
Williamstown Rural Lands ( WRL ) rurallands . org
WRL conserves and promotes the forests , fields , farms , and natural habitats of the region for the benefit of the community and future generations . The organization owns over 950 acres across 20 parcels and maintains 50 + miles of trails , which are wonderfully suited for families , novice hikers , and experienced outdoor enthusiasts . WRL hosts programs and events year-round , and their headquarters at Sheep Hill features walking trails , a nature cabin for kids , and the Dietze Interpretive Center , which offers interpretive exhibits and is the site of public programs throughout the year .
Stone Hill Trails
South Street , Williamstown Starting from the Clark Art Institute campus , the Stone Hill Trails offer fairly easy , classic Williamstown hikes . WRL Stewardship Director Dan Gura notes , “ Many of us have hiked to the top of the pasture just south of the Clark Art campus and have probably taken family or friends up there .” These trails provide some of the best views of the “ Purple Valley ” and are perfect for a leisurely family outing . The trails feature multiple trail junctions and pathways , including a trek to the summit that takes approximately 30 to 75 minutes round-trip , depending on which route you choose .
Field Farm
Sloan Road , Williamstown Managed by the Trustees of Reservations , Field Farm is a top choice for novice hikers . “ Field Farm offers big open meadows with views of Mount Greylock and loops that go into the forest ,” says Gura . Located in the south part of Williamstown , these hiking loops combine pastoral beauty with forest immersion , making them ideal for those new to hiking .
Berkshire Family Hikes berkshirefamilyhikes . com
Fitch Trail
Bee Hill Road , Williamstown For those seeking a more challenging hike , the Fitch Trail on Bee Hill Road stands out . Gura shares , “ The Fitch Trail , when combined with the RRR Brooks Trail for a 2.4-mile loop , has a lot of variety . It starts with views of Mount Greylock before leading through a deciduous forest to a dramatic ravine filled with hemlocks .” This hike takes about an hour and a half and offers a mix of terrain and scenic diversity .
Shepherd ’ s Well Trail
Mohawk Trail , Williamstown The Shepherd ’ s Well Trail is a moderately difficult 3.2-mile out-and-back hike that features excellent views of South Williamstown , the Hopper , Mount Greylock , and the Taconic Range . Gura adds , “ It ’ s an easy-to-moderate hike with good , dry footing and open areas with fantastic vistas .” Gura emphasizes the importance of being conscious and respectful while hiking . “ Stop and look around , and ask yourself why this place was conserved and what makes it special ,” he advises . “ Understanding the reasons behind trail creation and maintenance can deepen your appreciation for the landscape and encourage responsible use .”
Berkshire Family Hikes , founded by avid Berkshire-based hiker ( and regular Berkshire Magazine contributor ) Taylor Staubach , offers a wonderful assortment of outdoor activities throughout the year that specifically tailored for families . ( For more on their family-friendly events , see page 72 .) “ Our mission is to inspire families to get outdoors and reconnect with nature and to empower others to go outside with more confidence ,” says Staubach . Berkshire Family Hikes also provides trail reviews , tips , and educational resources to make hiking accessible for everyone .
Wild Acres
South Mountain Road , Pittsfield Located in Pittsfield and stewarded by the City of Pittsfield Department of Parks and Recreation with assistance from BNRC , Wild Acres is an ideal spot for family hikes . “ It ’ s a great hike because it ’ s kind of a figure-eight , so it ’ s very easy to loop ,” says Staubach . “ There ’ s a nice , a covered pavilion , so you could potentially sit and enjoy a picnic lunch there or something .” The 0.9-mile loop trail also features a pond , where children under 14 can fish without a license . ” A portion of the trail is fully mobility-accessible ,” notes City of Pittsfield Parks / Open Space Manager James McGrath . Maintained by Berkshirebased youth environmental action nonprofit Greenagers , it allows wheelchair users to
navigate from the parking lot down to the pond . A lookout tower overlooks the mountains and Pittsfield Airport , offering an exciting sight for both kids and adults .
Donato ’ s Way Trail
Route 20 , Lee Managed by the Lee Land Trust , Donato ’ s Way Trail is a 2.3-mile loop trail that leads past Lower Goose Pond . The trail is maintained through a partnership between Lee Land Trust and Trustees of Reservations . “ It ’ s a beautiful trail ,” says Staubach . “ It ’ s perfect for novice hikers and families seeking a longer , scenic hike .”
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