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Calderwood Trails Trailhead, part of the Freeport Conservation Trust, offers a serene, scenic destination for dog owners looking for pet-friendly trails in Freeport, Maine. Connected to the extensive East Freeport Trail System and Chase Reserve, this park invites visitors to explore a network of well-maintained, wheelchair-accessible, dog-friendly hiking trails with beautiful views of Maquoit Bay. Enjoy leisurely walks, water access via stairs to the shore, and a peaceful natural environment ideal for both you and your furry friend.
The park features numerous benches, shaded picnic tables, and a historic area featuring an old fireplace—a perfect spot for lunch breaks or a picnic with your pup. While parking is limited at the trailhead itself, there is overflow street parking nearby. The area is clean, well-maintained, and offers plenty of opportunities for outdoor activities including frisbee golf, a playground for kids, open fields, and ongoing improvements for accessibility. Calderwood Trails makes for a unique community hub for dog owners and families alike in Freeport.
Wow! Such amazing work has been done on the trails here!! They’ve graded out all the paths and made some spots that I think will eventually have benches in them. The idea is to make the trail super accessible, even for wheelchairs. I’m so impressed.
Enjoyable and mostly easy hiking in this area. Connects to a number of other trails in the East Freeport Trail System, as well as, Chase Reserve. Parking is limited to one space but the website says “you can park on either side of Flying Point Road near the Brunswick town line”. There are multiple benches and picnic tables. Definitely take the portion of the trail across the road from the trailhead. It’s a short walk to the water with stair access to the shore.
The larger Calderwood Trail loop connects to a patchwork of properties with a network of trails managed by Freeport Conservation Trust. We walked 4.5 miles and could have doubled that. The short loop across the road has views of Maquoit Bay through the trees and access to a small rocky bit of shore via some wonky wooden stairs. Bonus – there are picnic tables on both loops.
Great trail head
Aug. 15, 2021 – 1st time stop ! This is a scouting trip, to find this trail.
In Freeport, parking limited to 1 car and 1 motorcycle. Only walked in about 200 yards. . . Trailhead marker.
Old fireplace with a picnic table !
Lunch break!
Will get back to this on another day.