Hiking Trails and Maps

A trail kiosk at middle distance in a green summer forest, framed by dark tree trunks and leaves.

Cool hemlock forests, burbling brooks, and scenic vistas beckon you from all across the Hilltowns. Whether you’d like to sit and listen to the birds or take a long hike complete with steep boulder scrambles, you can find your next Hilltown adventure here.

Take Care When You Visit

All of these properties are open to the public from dawn to dusk.
No motor vehicles, with the exception of snowmobiles on established snowmobile trails, are allowed. Contact your local snowmobile club for details.
Dogs are welcome on all properties, with the exception of the Historic Dam Trail. Please keep dogs leashed when others are near. Pet owners must remove pet waste.
Please contact us if you notice any problems on our trails such as downed trees or washed-out bridges.
Visit the pages below for specific usage information, directions, and maps of each trail.

Scenic views of hills in autumn.

Big View

WILLIAMSBURG

Sweeping valley views from a Hilltown hidden gem.

Big View Map & Info

Nichols Brook at the Bradley Property in the fall

Bradley Sanctuary

WILLIAMSBURG

Choose your own adventure on a crisscrossing woodland trail network.

Bradley Map & Info

Fallen tree crosses a woodland stream at the Breckenridge property

Breckenridge Sanctuary

WILLIAMSBURG

Blake Brook and the Mill River’s trout-stocked West Branch border a 1-mile forest loop.

Breckenridge Map & Info

A view of the distant Holyoke Range mountains from the top of Briar Hill/Clary Hill.

Clary Hill

WILLIAMSBURG

Stacked loops range in difficulty, offering varied habitats and views.

Clary Hill Map & Info

Pond in the center of the property is still with trees and the sky reflecting. The foliage is colorful with some reds, yellows, oranges, and greens seen in the trees around the pond. At the edge of the pond you can see small grasses alluding to a different wetland habitat.

Conwell Property

WORTHINGTON

Watch the seasons change from a peaceful pondside perch, or climb Eagle Nest Ridge for a bird’s eye perspective.

Conwell Map & Info

A warmly dressed man poses with his arms flung open, gazing up at a giant snow-ringed boulder.

Hilltown Boulders

ASHFIELD & GOSHEN

Massive glacial boulders and a distant wetland view along a figure-8 loop.

Boulders Map & Info

A line of hikers single file on a wooded trail

Historic Dam Trail

WILLIAMSBURG

Climb to the remnants of the dam that caused the 1874 Mill River flood.

Historic Dam Map & Info

A trail sign nailed to a tree reads "Locke's Loop," with an arrow pointing left.

Locke’s Loop Trail

WILLIAMSBURG

Steep hillside trails and specimen trees near the center of Williamsburg.

Locke’s Loop Map & Info

Lush leafy trees and mossy rocks frame a woodland stream full of small cascades.

Robert’s Meadow Brook Trail

WESTHAMPTON

A wide woodland trail traces a burbling brook.

Photo by Lauren Katz.

Robert’s Meadow Brook Map & Info

A shagbark hickory with peeling bark frames a blue sky and grassy green summit clearing.

Round Top Hill Trail

CHESTER

Shagbark hickories and summit vistas atop the high point of Hampden County.

Round Top Hill Map & Info

Stevens Property

HUNTINGTON & WESTHAMPTON

Beavers, moose, and scenic vistas await on nearly 5 miles of rugged trails.

Stevens Map & Info

A small waterfall cascades over green mossy rocks.

Waterfall Trail

CUMMINGTON

A gentle ramble to a seasonal cascade at Two Mamas Farm.

Waterfall Trail Map & Info