Freeport Trail Challenge
Celebrating 10 Years of Exploring our Community Trails!
What is the trail challenge?
We invite you to explore four local trails with our exciting trail challenge!
Each year the Freeport Conservation Trust invites the public to take the challenge of hiking four trails selected from the variety of FCT and other public access trails in Freeport. It’s an opportunity to enjoy the beauty that these lands have to offer and earn rewards for getting outside. What could be better than that?
To celebrate our 10th anniversary of the Trail Challenge, we have added our first ever StoryWalk® at Florida Lake and trivia questions at River’s Edge, particularly with our awesome young hikers in mind!
What can I earn from doing the challenge?
Complete the Trail Challenge and submit your passport to enjoy a special treat, courtesy of Ben & Jerry's, Liberty Graphics, or Pet Pantry of Freeport, for our four-legged friends—you’ll get one of these prizes just for turning in your passport!
We are also running a weekly raffle drawing starting August 19th that features prizes from local businesses, including Wilbur’s of Maine, Patagonia, Island Treasure Toys, and L.L. Bean. After submitting your completed passport, you will automatically be entered into the raffle drawings—so, the earlier you complete the Challenge, the more chances you have to win!
Okay, I’m ready! How can I participate?
Grab your passport from the locations listed below and get outside! On each of our four trails, there is a stamping station with a unique rubber stamp. Use these to stamp your passport in all four locations, then return it to us! You can drop it off in the box in front of our office or submit it online using the button. Remember, you’ll get a prize just for turning in your passport—and you might win more in the raffle! Passports are available at the Freeport Town Hall, Freeport Public Library, Freeport Community Services, and Casco Bay YMCA. You can also print your copy or contact us if you’d prefer to have your passports mailed.
The 2025 Trails
Address: 49 Ringrose Rd
From Main St. turn onto Bow St. for 1 mile, continue onto Flying Point Rd. for 0.5 miles, then turn left onto Pleasant Hill Rd for 1.8 miles. Turn right on Ringrose Rd for 0.2 miles. Parking and trail head located on the left. The trail is approx. 0.7 miles.
This trail starts with a short, hilly loop followed by a leg out to Kelsey Brook—it also connects to the Jackman and Forest Ridge Trails.
Brimstone Hill Trail
Address: 236 Flying Point Rd.
From Main St. turn onto Bow St. for 1 mile, continue onto Flying Point Rd for 4.4 miles. Parking area and trailhead located on the right. Trail is approx. 0.3 miles.
The Calderwood property includes an eastern loop on one side of the road with views of Maquoit Bay, and a 1-mile loop trail on the western side of the road. From the rear of Calderwood there is a connection west via Moose Crossing Trail to Litchfield Road and north to Brunswick Topsham Land Trust’s Chase Reserve.
Calderwood
Address: French’s Run
From Main St., take left onto Route 136 north for 1.2 miles. At the blinking yellow light, turn right onto Route 125. Drive 2.4 miles and then turn right onto French’s Run. Trailhead and parking area are 0.1 miles on the left. Trail is approx. 2 miles around the entire orange trail.
From the parking area a flat path provides easy access to the lake. Hiking trails branch off the gravel path and pass through mature forests and by wetlands and streams.
Florida Lake
This trail features our first-ever StoryWalk®!Address: 114 Old S. Freeport Rd.
From Main St. take US-1 South for approx. 3.4 miles. Turn left onto Old South Freeport Rd. for 0.2 miles, then turn right into the YMCA parking lot. Trail is approx. 2.5 miles round trip
to the marsh and back.
A cooperative project of FCT and the Casco Bay YMCA, the 0.6-mile trail passes over hills and boardwalks to the marshy shore of the Cousins River. Side trails lead to/from Lambert Road and the Freeport Inn and Cafe.
River’s Edge Preserve
FAQ’s
How long will the challenge take to complete?
Trail challenge trails tend to be very manageable for the average hiker. You can complete the challenge as quickly or as gradually as you like. Some of our participants do the challenge in a marathon completing all the trails in one day. Others take a more leisurely route and do one trail a day. We encourage and see the merits in both approaches. Just have fun with it, no matter what you do.
Do I have to hike all four trails?
Only if you want to be eligible for prizes. Hiking and getting close to nature it is own reward, and if you only have time for one to three trails, we encourage you to still participate. Remember, we love any opportunity to see the pictures you take along the way!
Hiking Tips
1. Don’t Get Lost
It is important to take appropriate precautions when hiking, especially if you are unfamiliar with the territory you are in. Study maps, have a compass, and pay attention to your surroundings to avoid getting lost. Following trail signs like white blazes on trees will help get you home if you are not sure where you are. A good rule of thumb to remember is that a white blaze will normally mean you are on a main trail. If you are seeing blue blazes it likely means that you are on a spur or alternate route (Please note, there are exceptions to every rule).
2. Wear Bright Colors
We all know that starting in November wearing blaze orange in the woods is a good idea. Bow Season in Maine starts in September, and Maine residents can take to the woods with firearms in late October. Whether you are a hiker, a hunter, or just taking a day in the woods, it is always best to err on the side of caution.
3. Take Proper Precautions
Hiking is a more enjoyable adventure if you have the proper supplies. Proper shoes cannot be overstated here! Remember to have water and snacks with you and you’ll find your experience to be much more fun. Wearing a bug deterrent and doing a tick check at the end of each hike is also a good idea.
4. Leave No Trace
Always carry out what you carry in. Many of our trails are available because private landowners were generous enough to share the beauty of their land with all of us—be respectful of their hospitality. Always stick to the designated path and pick up all trash and dog waste so that everyone can enjoy the trails. As the famous saying goes: “Take only pictures, leave only footprints.”