Are you up to the CHALLENGE?

The Rules

Please take a moment to read all of the rules before signing up for this challenge.


  1. You have one day (or 24 hours) to complete this challenge.
  2. You must submit a GPX file for verification. Sorry, screenshots and a “trust me I did it, dude” will not suffice.
  3. Here’s a GPX file of the challenge (you do NOT have to do it this way):
  4. Here’s a link to the Strava:
  5. The following trails must be completed in their entirety:
  • BOTH sections of Blue within the park’s boundaries (all of the Regicides Trail and the Quinnipiac Trail from Paradise Road to where it leaves the West Rock Ridge SP boundary- there is an unmarked trail coming off the Quinnipiac that brings you to the Sanford Feeder Trail (one of the Blue/Red trails), this can be considered the “extreme NW boundary” of the park)
  • Red
  • White
  • Purple (but not all the way out to Main Street, I have taken out short sections like this that “dead end” at useless trail heads- you can do it if you want)
  • Orange
  • Green
  • Yellow (the one off Mountain Road- you do NOT have to complete the “road” section of this trail unless you want to)
  • White
  • Teal
  • Blue/Red (also called “Sanford Feeder Trail”, you do NOT have to go all the way to the gate)
  • Blue/Yellow: okay, this is super confusing because there are THREE Blue/Yellow trails, one on the north side of the park, one coming up from the Woodbridge side and one on the south side of the park. Yes, WTF indeed. You do not have to complete all three trails- just the one at the south end of the park and ONLY to where it intersects with the Regicides on one end and the Teal trail on the other. That is confusing AF, I know. Wait until you hear about...
  • Blue/White (ugh this one is so shitty- okay, on the map it’s labeled as “Gold” trail but the blazes were always yellow so we all confused it with the real Yellow trail off Mountain Road. Whatever, it’s Blue/White now).
  • Red/White (ugh, again- there are THREE Red/White trails in the park, one towards the south end, one to the east of Lake Wintergreen and one towards the north end.)
    • South Red/White (must complete ALL of this trail)
    • Middle Red/White (must complete ALL of this trail)
    • North Red/White (you do NOT have to complete the section out to the Hill Street trailhead labeled P)
  • Purple/White
  • Purple/Orange
    • optional trails: the new NEMBA Trail and the Black Diamond trail that the blazes just kind of disappear but still faintly goes up to Judges’ Cave. These can be used if you don’t want to do little out-and-backs or retread trails you already did. They may add miles, they may subtract miles. Your guess is as good as anyone’s here.
    • basically you DO NOT have to complete any trail that dead ends at a trail head, they add pointless extraneous miles

BELOW IS THE PARK MAP, please note above that some of the trails on the map have changed their blazes- CT DEEP has not updated this map since 2016. I could apologize for them but I won't since they can do better.

For a more detailed version of the map, go to CT DEEP's official West Rock Ridge SP website here:

West Rock Ridge State Park

You decide where you start and where you finish- submit GPX files or Strava links to: for verification

To enter: 

1) e-mail to say "I'm in" (you can also use the link on the CONTACT page on this site).

2) You will then get instructions on how to pay (it's only $20! PayPal or Venmo please) and the rest is then up to you!

3) your name will be listed on this here site for perpetuity and you will receive your award in the mail starting June 15th, 2021.


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