Posted on December 29, 2013 and last updated on February 10, 2019

South Freeport Trails, Freeport


  • Preserve Size: +155 acres
  • Trail Mileage: ~5 miles in network
  • Pets: yes
  • Difficulty: easy
  • Sights: woods, fields

This is a marvelous network of trails — roughly five miles total — that are equally great to ski, snowshoe, or hike. The Freeport Conservation Trust’s maps and trails are excellent. My map pales in comparison. No matter! Go out and enjoy. The main network consists of Bliss Woods Trail, Stonewood Trail and Sayles Field, with a little side trip of Ridge Trail if you’re up for it. There is a bit of a view of the sea from the apex of Ridge Trail. For a great walk, start at Bliss Woods and loop around Sayles Field, returning either the way you came or back along the road. 

Directions: To start at Bliss Woods, park at the trailhead and lot on the north side of the South Freeport Road, about 0.5 mile from the “Big Indian” statue on Route 1. Look for the Bliss Woods sign. Or you can park at the end of Stonewood Road, off of Route 1. The most ambiguous place to park is near the Ridge Trail/Sayles Field trailheads. I think you’re meant to park on South Freeport Road, in front of the post office, school, or church…but I’m not sure. If you can, start at the other two trailheads.