Backpack Trail Guide

Trails / Massachusetts / Berkshires

Appalachian Trail: Upper Goose Pond to Dalton (US 20 to Gulf Road)

Appalachian National Scenic Trail and October Mountain State Forest area, central Berkshires (Lee, Becket, Washington, and Dalton)

North of the Massachusetts Turnpike, the AT settles into quieter country: a run of wooded summits, beaver ponds, and Finerty Pond, then a walk through the town of Dalton. New England Waterfalls, which rates Massachusetts backpacking spots, calls the middle of the state’s AT “quieter but less interesting” than the ends, and expects low to moderate crowds at the October Mountain Shelter.

It’s a good two-day trip, with two large shelters spaced about 9 miles apart.

The hike

From the Route 20 trailhead in Lee, a blue-blazed trail crosses the highway and reaches the AT in about 0.1 mile, according to Berkshires Outside. If you’re coming from Upper Goose Pond, the cabin side trail is 1.6 miles south of the road (see the previous section).

Northbound, Berkshires Outside puts the summit of Becket Mountain, marked by the foundation of a former communication tower, at 1.4 miles. The trail follows the Walling Mountain ridge, which n2backpacking calls “overgrown,” then makes a steep descent to Finerty Pond at 2.8 miles. Berkshires Outside says the pond’s mountain laurel “is spectacular when in full bloom in late June.” An AMC Outdoors writer who walked this stretch southbound in 2020 passed a giant hemlock about a mile before the pond and described its calm water in the morning light. The trail crosses the School House multi-use trail, passes several beaver ponds, and reaches County Road in Becket at 4.1 miles.

The October Mountain Shelter is 2.2 miles south of Washington Mountain Road (Pittsfield Road on the DCR map). Berkshires Outside describes Bald Top, two logged Norway spruce plantations, beaver ponds, and Cady Brook, which can usually be crossed on stepping stones. Near the Washington Mountain Road trailhead, about 200 feet east, is Blueberry Hill Farm, “known by backpackers as The Cookie Lady’s House,” with seasonal pick-your-own blueberries.

From there it’s 2.8 miles to Blotz Road, then on to Grange Hall Road and the Kay Wood Shelter just south of it. The 2008 Hampden-Sydney trip report hiked 17.6 miles from the Upper Goose Pond Cabin to Kay Wood in a day.

North of Kay Wood, Berkshires Outside says the trail follows town sidewalks for almost two miles through Dalton, crossing the railroad tracks and Route 8A, before entering the woods at Gulf Road. Backpacker’s waypoints mark the corner of Main and Depot Streets near the hydroelectric plant and the CSX crossing at Housatonic Street. The Transcending Mountains author stopped at a Cumberland Farms in Dalton for supplies.

The section ends at the Gulf Road trailhead. The next section north climbs to Crystal Mountain and Mount Greylock.

Tips

Camping

The ATC says camping in Massachusetts is restricted to designated sites, and AMC Western Massachusetts says stealth camping isn’t permitted. Sites are first come, first served. The DCR map limits camping groups to 10 and stays to two consecutive nights at any site. Fires are allowed only in central fire rings (AMC Western Massachusetts).

Sites in this section (AMC Western Massachusetts):

Inside Intel: No camper accounts recommending one of these sites over the other were found. New England Waterfalls rates October Mountain Shelter 6 of 10 for scenery and expects low to moderate crowds there, fewer than at the sites on either end of the state.

Trail facts

The Lowdown

Beaver ponds below Bald Top:

Between Finerty Pond and Dalton, nearly 19 miles of wooded ridge pass beaver ponds and Cady Brook, with just two shelters to duck into. See how three rain shells compare, and whether the priciest one is worth it.

Read the comparison →

Where this comes from

This page draws on the sources below, along with other guides and trip reports. Links go to the original pages.

Before you go: This page is based on published trail guides, trip reports, and reviews, along with official park and agency information where we could find it. It’s meant to help backpackers discover new trails, not to replace current, official information. Conditions, closures, permits, campsites, and water sources change, and some details here may be out of date or wrong. Confirm everything with the managing agency and check current conditions before you head out, and don’t rely on this page alone for safety or navigation. Backcountry travel involves risk.