Shelton Trails Letterboxing Challenge

Our latest trail challenge involves a Victorian-era pursuit called "letterboxing." We've hidden twenty containers, one on each of our named trails, and you can find them using our clue packet. Each container holds a hand-carved rubber stamp, a logbook where you can record your visit, and a small pad of ink. Use the rubber stamp and ink to mark the clue packet in the space provided, or use a logbook of your own. There is no time limit for this challenge. 

We recommend that you also create a trail name to identify yourself and carry a personal "signature stamp" so you can "stamp in" to the letterbox logbook. 

  • CLUE PACKET - quick view (version March 18, 2021)
  • CLUE PACKET PDF version March 18, 2021 for printing (also, preprinted versions with maps attached are available at City Hall by the front door). NOTE: This packet may be updated from time to time if hiding locations need to change. 
  • REVISIONS/CORRECTIONS: 1. Nells Rock Trail was mistakenly said to have a red blaze in the February version. The blaze color is white. 2. Oak Valley Trail was rerouted on March 17, 2021, so the original box is now about 90 steps down the old road after the reroute junction. The original box will remain there for people who have older clue printouts, but a second mirror box was hidden along the new Oak Valley Trail route. 
  • Trail maps for printing
  • Trail map on Google Maps (for navigation and geolocating yourself on the trails)
  • (most active letterboxing site with lots of clues)
  • (the first letterboxing site, many older clues are listed here)
  • Letterboxing FAQ
  • AQ Map of our letterbox locations 

Contents of Letterbox #18  Little Pond Trail

The rubber stamps: Each stamp was hand-carved and has the number and name of the trail it's hidden at. There are three basic designs: One for trails mostly on City of Shelton Open Space (featuring an outline of the City of Shelton); one for trails in CFPA's Connecticut Blue-Blazed Trail system (featuring CFPA's blue oval); and one for trails that are accessed via Shelton Land Trust property (a rectangle with pine trees on either end, which the Land Trust uses on their property signs).  

Clue packet stamped with #15 Poet Path

Finding more letterboxes: There are many other letterboxes hidden along the trails in Shelton. Clues for these letterboxes may be found at the two letterboxing websites ( is used more often, while has listings for many older boxes).  Note that clue listings for many sensitive boxes will be hidden from beginner letterboxers at first, but after some "finds" have been logged into the website, these clue listings will begin to reveal themselves. 

Stamp hidden at Indian Well

A "signature stamp"
There is no deadline for this challenge. Take as long as you want. 

The stamps and clues for our challenge are simple, but if you look, you may find more artistic carvings hidden along the trails, and clues that may be in the form of riddles or puzzles. 

Most beginners use a store-bought stamp as their first "signature stamp." This is the stamp you use to represent yourself when signing in to the letterbox logbook. Most letterboxers eventually switch to a hand-carved stamp. 

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