Fairfield County Letterbox Trails for Kids

Letterboxing with Kids in Fairfield County

So maybe you've heard about it but you're still not really sure. What is letterboxing anyway? Well to start, it is really like the ultimate scavenger hunt. You are given a set of clues and then you head out into the woods and go on a hunt in search of secret hidden stamps in the forest. Sound fun? That's because it is! Even my three year old is a letterboxing-enthusiast.

This fun family adventure is great for all ages and for all cities located across the country. There are about 90,000 active letterboxes hidden in North America alone. So what exactly is a letterbox? Letterboxes are small weatherproof boxes that typically contain a hand-carved rubber stamp, a log-book to keep a record of visitors, and occasionally an ink pad. Letterboxer's will leave an imprint of their own personal stamp in the letterbox's log book. We've rounded up six kid-friendly letterbox trails in Fairfield County. Happy Trails.

Earth Place - Westport
Five boxes are hidden (easily) along Earth Place’s Swamp Loop Trail, which is about a 30 minutes hike (or hour hike with toddlers.)  Winding past a swamp, a freshwater stream, a pond, and deciduous woodlands, the Swamp Loop Trail is beautiful during the spring and summer months for viewing wildflowers. Some boxes require a compass. A limited number of compasses are available to borrow from the museum front desk.

10 Woodside Lane Westport 06880

Stamford Nature Center - Stamford
The Forest Letterboxing Trail will take you to some of Stamford Nature Center’s very favorite spots.With six forest-themed boxes hidden under boulders, mossy roots, and inside old tree stumps, you’re sure to spend an entire afternoon exploring the nature center’s trails. Clues for the boxes are lent out from the Overbrook Nature Center or the Bendel Mansion. Be sure to return the clue sheet and head to the nature center’s playground before heading home.

39 Scofieldtown Road Stamford 06903

Discovery Museum - Bridgeport
Looking for a far-out trail? Head to the Earth and Sky Discovery Trail located behind the Discovery Museum on upper Park Avenue in Bridgeport for Solar System-themed letterboxes. There are 10 boxes hidden along the trails for each planet and space. Also, the Earth and Sky Trail is a constellation-themed trail with six letterboxes hiding stamps that represent a zodiacal constellation coupled with it’s complementary opposite sign.

4450 Park Avenue Bridgeport 06604

Webb Mountain Discovery Zone - Monroe
Head to Webb Mountain Discovery Zone for a six box series based on the "Land Before Time" series of movies. That’s right, along the trail you’ll find Ducky, Cera, Littlefoot, Spike, Chomper and Petrie. You’ll start at Froggy Freeway and pass along trails like Salamander Street and Hawk Highway. You’ll all have a dino-mite time.

71 Webb Circle Monroe 06468

Shelton Lakes Greenway Trails - Shelton
Hungry? Why don’t you head to the lake for a burger? A too-good-to-eat letterbox series called “Build-a-Burger” is hidden along Hope Lake, which is part of the Shelton Lakes Greenway trails. There you’ll find everything you need from the bun to the tomato to the burger and cheese. There are six boxes in all (the last being a veggie burger!) For those of you who are more of a hot dog lover, checkout the “Footlong” series. And if you would rather get right to dessert, look for “I Scream For Ice Cream.”

Hope Lake Nells Rock Rd. Shelton 06484

Connecticut Audubon Society Center - Fairfield
Hidden throughout the grounds of The Connecticut Audubon Society Center at Fairfield is a kid-friendly letterbox series called “Something’s Buggin’ Me.” Five bug-themed boxes with ladybugs, bumblebees, dragon flies and more are tucked along tulip trees, fallen trees and over bridges. The trip could take up to two hours or you can make a day of it if you care to check out the wildlife on the trails, check out the “Birds of Prey” Compound and enjoy a pond-side picnic.

2325 Burr Street Fairfield 06824

Photo by Webbdiscovery via Instagram 

Earth Place
10 Woodside Lane
06880 Westport , CT
Phone: 203-557-4400
41° 8' 43.7028" N, 73° 22' 51.4524" W
Stamford Nature Center
39 Scofieldtown Road
06903 Stamford , CT
Phone: 203-332-1646
41° 7' 33.9636" N, 73° 32' 43.854" W
Discovery Museum
4450 Park Ave
06604 Bridgeport , CT
Phone: 203-372-3521
41° 12' 56.6532" N, 73° 14' 1.4856" W
Webb Mountain Discovery Zone
71 Webb Circle
06468 Monroe , CT
Phone: 203-556-9737
41° 21' 41.004" N, 73° 10' 12.6984" W
Hope Lake
Nells Rock Road
06484 Shelton , CT
Phone: 203-924-1555
41° 18' 12.5496" N, 73° 6' 52.02" W
Connecticut Audubon Society Center at Fairfield
2325 Burr Street
06824 Fairfield , CT
Phone: 203-259-6305
41° 12' 6.5772" N, 73° 17' 32.5248" W