Posted on November 29, 2013 and last updated on December 16, 2022

East Freeport Trails


  • Preserve Size: Not sure
  • Trail Mileage: ~10 miles in network
  • Pets: yes
  • Difficulty: easy to moderate
  • Sights: brooks, woods, forest wetlands, Maquoit Bay view

(East Freeport trails in blue, Calderwood Preserve in light green, and Chase Reserve in green)

The Freeport Conservation Trust has done a great job of linking conserved lands to make for substantial walks in quiet places. In this network, which is about ten miles in all, the Brimstone Trail connects with the Kelsey Brook trail, Gibby’s Trail, Antoinette Jackman trail, Calderwood Preserve trails, and Chase Reserve trails. The land trust asks walkers to stay on marked trails since some of the trails cross private land.

A few highlights are the Antoinette Jackman trail, which takes you to the upper reaches of the Little River, the Kelsey Brook trail, along the pretty stream, and the Mitchell Ledge Trail (no dogs allowed), with views over farm fields. Note that the trails on the western side do not allow dogs. While most of the trails are easy, there are some ups and downs along Kelsey Brook and Mitchell Ledge trails.

Note: In the winter of 2019, I could not find the trailhead for Bessie’s Trail, on Litchfield Road, and so just crossed a field to reach the road when the trail ended at a farm.

Part of the network on the western side does not allow dogs.

Directions: There are several ways to access these trails. If you start at Brimstone, turn onto Ringrose Road from Pleasant Hill Road. The trailhead and parking area are on the left, 0.2 miles down Ringrose Road. If you start on the other side, bear right from Bow Street (if you’re coming from downtown Freeport) on Flying Point Road; turn left onto Litchfield Road. Continue down Litchfield Road until it makes a sharp left, and look for a small parking area on your left.