Appalachian Trail: Jug End to Upper Goose Pond (Jug End Road to US 20)

Appalachian National Scenic Trail, Beartown State Forest, and the Upper Goose Pond area, southern Berkshires (Sheffield to Lee)

The middle of the southern Berkshires is the Massachusetts AT at its most varied: farm fields and the Housatonic River, a boulder-choked ravine, Beartown State Forest’s Benedict Pond, and, near the end, Upper Goose Pond and its cabin. It’s also long. The DCR’s map puts Jug End Road at mile 9.5 from the Connecticut line and US 20 at mile 43.0, so plan on three or four days.

Five overnight sites line the way, from shelters to tent platforms to a cabin with bunks.

The hike

From Jug End Road, the trail crosses the valley floor. SectionHiker’s Philip Werner describes forest, then marshland, then farm fields, past the monument to Shays’ Rebellion, the 1787 farmers’ revolt, before reaching Route 7 and the Housatonic River. The DCR map has the trail crossing Route 7 at mile 14.0 and Homes Road (spelled “Holmes” on the map) at 16.9.

From Homes Road, an AMC Outdoors writer describes a steep climb to the East Mountain ridge and a flat boulder overlooking the Taconic Range and the Housatonic Valley, then Ice Gulch, with massive glacial boulders. The Tom Leonard Shelter is 1.1 miles south of Lake Buel Road, per AMC Western Massachusetts. The Transcending Mountains author noted a steep final mile up to it.

After Route 23, the trail enters Beartown State Forest. The 2008 Hampden-Sydney trip report photographed irises and mountain laurel at Benedict Pond, and AMC Western Massachusetts places the two Wilcox shelter areas 1.3 and 3.1 miles north of the pond. The Transcending Mountains author enjoyed views from “the Ledges” toward East Mountain and the Catskills, and passed the Cooper Brook beaver pond farther north.

The Shaker Campsite comes next, 0.3 mile north of Fernside Road in Tyringham. North of Goose Pond Road, Berkshires Outside describes stone walls, a long bridge over Cooper Creek, an old beaver pond, and Higgly Brook. The side trail to Upper Goose Pond Cabin is 3 miles from Goose Pond Road and 1.6 miles south of Route 20. The cabin sits half a mile off the AT.

The last stretch crosses the Massachusetts Turnpike on a footbridge reached by two spiral ramps, passes the Greenwater Pond dam, and climbs steps to Route 20 in Lee.

The 2008 trip report broke this stretch into three nights: Hemlocks to Tom Leonard (14.4 miles), Tom Leonard to Shaker (11.2), and Shaker to the cabin (9.9).

The section to the south is Sages Ravine, Mount Everett, and Jug End, and the next one north runs from Upper Goose Pond to Dalton.

Tips

Time the cabin. Upper Goose Pond Cabin is staffed from mid-May to mid-October and closed otherwise; the tent platforms stay open year-round.
Groups should skip the cabin in July and August. AMC Western Massachusetts says it’s intended for individual AT hikers.
Guard food at Shaker. AMC Western Massachusetts notes bears there and says not to leave food unattended, even briefly.
Check water late in the season, especially at Wilcox North.
Plan parking. Overnight parking isn’t recommended at the Route 20 trailhead.

Camping

The ATC says camping is restricted to designated sites in Massachusetts. Sites are first come, first served, with no stealth camping (AMC Western Massachusetts). The DCR map limits camping groups to 10 and stays to two consecutive nights at any site. AMC Western Massachusetts allows campfires only in central fire rings, and none at Upper Goose Pond Cabin.

Sites, south to north (AMC Western Massachusetts):

Tom Leonard Shelter: sleeps 12; 5 tent pads, 2 platforms; water 0.16 mile downhill.
Wilcox South: small shelter (4) and large shelter (12); 5 tent pads; small spring.
Wilcox North: older log shelter (8), room for about 4 tents; water may be dry in late summer.
Shaker Campsite: 2 platforms, room for about 5 tents; water 100 yards north.
Upper Goose Pond Cabin: caretaker mid-May to mid-October; 4 tent platforms year-round, 2 privies, bear boxes.

Inside Intel: The cabin is the stop hikers write home about. The Transcending Mountains author, arriving after a 27-mile day in 2013, described “wonderfully padded bunks, and real furniture,” pancakes and coffee in the morning, a dock, and a beach. The Hampden-Sydney trip report also photographed the pancake breakfast, and the ATC says the caretaker may serve one to overnight guests.

Trail facts

Distance: About 33.5 miles, Jug End Road to US 20 (DCR map)
Route type: Point to point
Difficulty: Moderate to strenuous
Campsites: Tom Leonard, Wilcox South, Wilcox North, Shaker, Upper Goose Pond Cabin and platforms
Water: Springs, brooks, and ponds; treat all water
Permits: None; first come, first served
Group size and stays: 10 people; two consecutive nights per site (DCR map)
Fires: Fire rings only; none at Upper Goose Pond Cabin
Trailheads: Jug End Road; Route 7, Homes Road, Lake Buel Road, Route 23, Goose Pond Road; US 20 in Lee
Last verified: October 8, 2026

The Lowdown

Marsh to mountain between Jug End and Lee:

Three or four days through marshland, Ice Gulch, and Beartown State Forest is a long stretch to carry a shell you aren't sure of. We compared the Arc'teryx Beta SL with two less expensive options.

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.