2017 Lollipop League Challenge

Join the Lollipop League Challenge

Path Tag
Deadline extended to June 2, 2018

This year the Shelton Trails Committee is inviting everyone to join the Lollipop League as our annual trails challenge. In hiking/trails terminology, a “lollipop” trail is one that starts at a location/parking place, progresses to a point, makes a circle/loop back to that point, then back to the starting location. As a result, this is a very family friendly challenge in that everyone can drive to the starting point, do the hike, and return to the car for the ride home. While most of the 12 hikes are shaped reasonably like a lollipop, some require a bit of imagination to qualify. But our goal is to get people hiking at locations all over Shelton, some of which may be new to those that only use our trails in their neighborhood.

The following have completed all twelve hikes and are full members of the Shelton Lollipop League:
Gary Plude
Val Gosset

Teresa Gallagher
Todd Edwards
Kim Edwards
Colin Edwards
Addy Edwards
Sheri Dutkanicz
Terry Gallagher
Bill Dyer
Casey Louise Thomas

Participants will use our form to log each completed trail by listing the date each trail is hiked. The form can be used for up to four hikers, both two and four legged. All hikers are on the honor system to fill in their form. The official kickoff date is June 3rd, when we will host a guided hike starting at Pine Lake in honor of National Trails Day. Other guided hikes of Lollipop Trails will be scheduled until November and our annual Turkey Trot Trail Hike on the Sunday after Thanksgiving.

This event is open to residents and non-residents of Shelton. No signup is required; hikers just download and print the form and view/print the 12 official maps from this website or obtain copies at the Shelton Community Center. Once hikers complete the 12 trails, they can mail the form to the address listed on the form, or it can be scanned/photographed and emailed as provided on the form. All hikers completing the challenge will be sent a commemorative path tag, and names will be listed on our blog.

1. Use the Lollipop League Hike Form to record when you have completed each hike (available on this website and the last page of the pre-printed packets). 

2. Hike the twelve loop trails listed below in any order you like. Be sure to check the hike maps and descriptions to walk the correct route. Updates and trail conditions will be listed online. All the hike maps and descriptions below can be downloaded as one .pdf file HERE and are also included in the pre-printed packets available at the Community Center).

 1. Oak Valley Trail (2.1 miles)
 2. Dog Paw and Flower Paths (1.7 mi.)
 3. Turkey Trot Trail (2.0 mi.)
 4. Nicholdale Farm (1.3 mi.)
 5. Birchbank Trail (2.0 mi.)
 6. Tahmore Loop (1.6 mi.)
 7. Pine Lake to SIS Bypass Loop  (2.3 mi.)
 8. Lane Street Rec Path to Basil Brook Bypass (3.2 mi.)
 9. Abbey Wright Loop (1.5 mi.)
10. Boehm Pond Loop and Spur (1.0 mi.)
11. Paugussett Indian Well Loop (5.9 mi.)
12. Paugussett Buddington Loop (3.0 mi.)

3. Optional: We encourage participants to share at least one photo of their adventures with us. Photos may be posted on this blog and/or the Shelton Trails & Conservation Facebook Page. Email photos to conservation@cityofshelton.org.

4. Submit your completed form to: Teresa Gallagher, Conservation Department, City Hall, 54 Hill Street, Shelton, CT 06484. Forms can also be emailed to conservation@cityofshelton.org, or dropped off in Teresa's office Room 102. We will accept forms up through June 2, 2018. Be sure to include your mailing address so we may send you a commemorative path tag.


  1. Mom and Pop, download the Lollipop League form and maps, get out on the trails with your Munchkins and head out on the “Yellow Brick Road.” You will see wildlife along the way, but no lions, tigers and bears (Oh my!). Our trees will not throw apples at you. And unlike the totally loose Toto, your dogs are most welcome but on a leash. Plus there are lots of Letterbox and Geocache boxes along the 12 selected trails.

  2. Keep an eye out for the Shelton Troll geocache at the Pine Lake trail. :D

  3. I finished my hikes Sunday. Lots of people out enjoying the trails. Wonder if there will be any lollipops for the Thanksgiving Hike?