LocationsThe Berkshires
3 parks · 64 challenges · Massachusetts
Outdoor things to do with kids in The Berkshires
In Sheffield, Great Barrington and Lanesborough.
The highest point in the state, a quartzite peak you can see it from, and a ledge above the Housatonic with more ferns than almost anywhere.
Finish all 3
Play every park here and your family are Explorers of the Berkshires.
Where to go, and what to expect
Bartholomew's Cobble
Sheffield, Massachusetts · 21 challenges
Two rocky knolls above the Housatonic holding one of the greatest diversities of fern in North America, five miles of trails, and a hilltop field looking straight up the river valley. No dogs at all.
About 2 hoursBathrooms in season
Underfoot. Five miles of trails over two rocky knolls, open fields and marsh. Hurlburt's Hill climbs to a twenty-acre field at the top. The Trustees ask you to allow at least two hours.
Parking. Parking for thirty cars at the entrance on Weatogue Road. $5 a person for non-members and $1 per child aged 6 to 12; free for Trustees members. Sunrise to sunset.
Monument Mountain
Great Barrington, Massachusetts · 22 challenges
A pale quartzite peak with three short trails up it and the whole Housatonic valley laid out from the top — Mount Greylock one way, the Catskills the other, and hawks going past below you.
About 2.5 hoursNo stroller
Underfoot. Three trails, all under three miles. The Hickey Trail leaves north from the lot and is the most direct and the most strenuous. The Peeskawso Peak Trail is the summit connector and has the best views. This is a real climb — 1,642 feet at the top.
Parking. Entrance and parking for 56 cars on Route 7. $10 to park for non-members; free for Trustees members. Open sunrise to sunset. The lot is not maintained in winter. A free trail map is on the bulletin board in the parking area, when supplies last.
Mount Greylock State Reservation
Lanesborough, Massachusetts · 21 challenges
The highest point in Massachusetts, 3,491 feet up, with a lit stone tower on the summit and ninety miles of view on a clear day.
About 2.5 hoursBathrooms
Underfoot. Trails run from casual to extremely difficult — look at the map before choosing one. The park is dawn to dusk.
Parking. The Visitor Center is at 30 Rockwell Road and is reachable by car all year. The auto roads to the summit itself open mid-May to the end of October only, and are closed to anything longer than 22 feet.
Play all 3 around The Berkshires
Free. Works with no signal once you're there.