Gregory Trail is an easy 1-mile trail that loops around a heavily wooded 20-acre property with lengthy frontage on the Back River, an eastern branch of the Sheepscot River. There are extensive views to the north of the bridge which connects the Boothbay mainland to Barters Island, and across the river to the undisturbed wooded shoreline. Hikers can enjoy walking around a small pond bordered by wildflowers and edged with cattails. Bullfrogs and dragonflies revel in this natural habitat, as well as deer, small mammals, and a variety of birds. The trail meanders through widely varied woods, including evergreens, oak, maple, aspen, and birch.

Boothbay Region Land Trust (BRLT) has permission to maintain and provide public access to this trail through the generosity of the landowner, Dorothy Gregory. Because Gregory Trail traverses private property, visitors are asked to respect the privacy of the owner, as well as avoid disturbing or removing plants or wildlife.

From Boothbay Harbor go north on ME-27 to the roundabout in Boothbay Center; go around the roundabout and turn right onto Corey Lane. Proceed 0.3 miles. Turn right onto Barters Island Road and travel 1.7 miles, crossing a causeway. Turn left onto Sawyers Island Road. Proceed 0.5 miles to the entrance on the left.

The Maine TrailFinder website and the AllTrails website have descriptions and maps of hikes on the Gregory Hiking Trail/.