Freeport Trail Challenge 2026
THE TRAIL CHALLENGE
Each year, the Freeport Conservation Trust chooses four trails from Freeport Conservation Trust and Town preserves in Freeport.
Now, the trails are ready for you to explore! The Trail Challenge is an opportunity to enjoy the beauty that our lands have to offer and earn rewards for getting outside. What could be better than that?
The Trail Challenge runs from August 10th to October 13th. Please submit all passports either through mail, dropping off in the box in front of our office, or emailing them to trailchallenge@freeportconservationtrust.org
This year, we are bringing back the fabulous Story Walk® at Simpson Woods! We will also have trivia questions at Hidden Pond, with our amazing young hikers in mind!
THE INCENTIVES
In addition to the joy of getting outside, FCT has put together some fun prizes for completing the Trail Challenge. The first 200 participants to complete all four trails and turn in their passports will receive a voucher for the Freeport Ben and Jerry’s Scoop Shop!
Each participant will also be entered into a raffle for a grand prize, where they could win gifts from Patagonia, Wilbur’s, and Treasure Island Toys! We will pull two grand prizes, one for kids and one for adults.
HOW TO PARTICIPATE
Simply grab your passport and get outside! Passports are available to pick up at:
Freeport Town Hall
Freeport Public Library
Freeport Community Services
Casco Bay YMCA
Freeport Post Office
Or you can print your copy or contact us if you’d prefer to have your passports mailed. Once you have your passport, it’s time to get outside!
On each of the four trails, there is a stamping station with a unique rubber stamp. Find each stamp along the trail and use these to stamp your passport in all four locations, then return it to us!
You can drop off your completed passport in the Trail Challenge box in front of our office at 57 Depot St, Freeport, ME or submit it online using the green submit button on this page. Remember, the first 200 people to submit a completed passport will receive a prize!
The 2026 Trails
Jackman Woods
Trailhead: 3 Windpointe Rd at the end of Litchfield Rd (click address for google map directions)
Directions: From Main St. turn onto Bow St. and continue for 1.2 miles. Then continue on Flying Point Rd. for 1.3 miles. Turn left onto Litchfield Rd. and continue straight for 1.3 miles until you reach the brown trailhead sign on the lefthand side of the road. The trailhead and parking area will be located on the corner on the left.
Description: A peaceful loop on the Forest Ridge Trail through a wooded forest with rocky stream crossings and rooty terrain. This trail connects to the larger East Freeport trail network providing access to Kelsey Brook and Wescott Woods.
Approx. 45min- 1 hour walk
Mileage: 1.7 miles total | 0.75-miles to stamping station
Hidden Pond
Approx. 15-20 minute walk
Mileage: 0.4-mile loop | 0.25-miles to the stamping station
Address: 151 Grant Rd.
Directions: From Main St. take a left onto Route 136 north (Durham Rd). After 1.2 miles, you can access Grant Rd from either direction: continuing down Durham Rd. and taking a right onto Grant Rd after 2.4 miles OR taking a right onto Route 125 (Wardtown Rd.) and taking a left onto Grant Rd. after 3.3 miles. The flat dirt parking lot for the trail will be located about halfway down Grant Rd. (on right if coming from Durham Rd. on left if coming from Wardtown Rd.).
Description: A short, grassy loop leading to a scenic outlook of Hidden Pond, great for those interested in birding. The trail is flat and wide, great for all ages.
Simpson Woods
Address: 1528 U.S. Route One
Directions: From Main St. head north on Rte. 1 for 3 miles. The parking and trailhead are located on the right.
Description: Begins with an open fern forest, leading to a more rocky and rugged rolling loop with small stream crossings, narrow trails, and a variation in elevation. The stamping station can be found at the intersection of the white trail and the new blue trail loop. The blue trail features long sections of bog bridges across wetlands and passes several cascading streams.
Approx. 45min - 1 hour walk
Mileage: 1.36 miles total | 0.5 miles to stamping station
Brewer Woods
Trailhead:112 Flying Point Rd.
Directions: The trailhead is a small dirt driveway marked with a brown hiker sign. Coming from Freeport, it is the second driveway on the right. Parking is very limited (3-4 cars) at the trailhead.
Description: The trail begins at the small parking lot and travels alongside a private driveway for 100 yards. It proceeds on flat but rooty ground to an intersection with the Whippoorwill Woods Trail (which connects with Wolfe’s Neck Farm Trails). At the junction, bear right and continue down the slope and across a small bog bridge. After the bridge, there is a small loop trail that loops past a bench overlooking the Little River.
Approximately 30 min walk.
Mileage: 0.75 miles in total | 0.35 miles to stamping station.
Hiking Tips
1. Stay on Trail
When hikers venture off-trail to take a photo amongst wildflowers or take a shortcut down a hill, it can be hard to see the impact of those small choices. But over time, especially in places with a short summer season where plants only have a few weeks to grow and reproduce, these actions have a lasting impact!
Following the trail markers and staying on trail helps to keep our landscape protected so it will last long into the future, ensuring flowers, grass, and other plants thrive year after year.
In Freeport, we typically use white or blue blazes on trees. 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 be cautious.
3. Prepare for your Adventure
Hiking is a more enjoyable adventure if you have the proper supplies. Take a look at a map before you hit the trails, wear sturdy shoes and make sure to bring along enough water and snacks to help make the experience 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.” To learn more about Leave No Trace principles visit the link here!
Frequently Asked Questions
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. The entire challenge does not take more than 4 hours of active hiking. 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!
Thank you to all of our incredible community sponsors!
