New Canaan’s Winter Hiking Challenge


We challenge you to visit 7 New Canaan Land Trust preserves and complete 7 hikes this winter. Our preserves have much to offer year-round. Enjoy the fresh air, spot local wildlife, get your steps in, and ring in the New Year with 7 fantastic hikes.


  1. Visit and walk the trails at all or some of the preserves listed below 
  2. Take a photo of yourself (and your hiking buddy) at two locations at the preserve:
    1. Next to the welcome sign at the entrance to the preserve.
    2. At the special location described in the list below.
  3. Post your photos to Instagram/ Facebook, and tag #NewCanaanLandTrust 
  4. Keep track of your hikes on the chart, available for download to the right. Make sure to record the date of your hike, your name, and the names of your hiking buddies.

When you have completed all the hikes, or as many as you wish to complete, submit your information into the form on the right. Only submit this form once, after have completed the challenge up to your preferred level of participation

We encourage you to post your pictures on social media and to use the following hashtags:
#NewCanaanWinterHikingChallenge, #NewCanaanLandTrust, #NCLT #LoveYourCTLandTrust

All entries are due by 5pm on March 21, 2022


Active members of the New Canaan Land Trust (having made a gift of $50 or more in the last calendar year) are eligible for the following prizes.

  • Visit 4 properties and receive a New Canaan Land Trust car magnet
  • Visit all 7 properties and receive a car magnet, certificate of completion, AND be entered into a raffle to win one of two hand-carved walking sticks (similar to those pictured here).

Not a member? Become one today by clicking HERE.

Many thanks to Dennis Taylor for carving and donating the walking sticks.


Walk the trails at the following New Canaan Land Trust preserves, and snap a photo at the designated photo location.

1. Browne (info)
Photo location – Glacial Erratic Boulder
The boulder is located near north side of preserve. Walk the trail in a counter-clockwise direction for about a quarter-mile: you can’t miss the giant bolder along the trail.

2. Watson-Symington (info)
Photo location – Stone Labyrinth
The labyrinth is located just off the trail, between intersections D and E. Look to the east along this trail, and you’ll see stones arranged in the shape of a traditional seven-circuit labyrinth.

3. Livingston-Higley  (Info)
Photo location – Kestrel Nesting Box
Simply follow the trail from Apple Tree Lane until it opens to the preserve’s iconic meadow. The nesting box is mounted to a 15′ tall wooden post near the stone wall traversing the meadow.

4. Still Pond  (info)
Photo location – Council Ring Seating Area
From the Silvermine-Fowler entrance (763 Silvermine Road), follow the trail through the woods until you reach the newly-planted pollinator meadow. The council ring seating area is adjacent to the meadow, overlooking Still Pond.

5. Colhoun (info)
Photo Location – Wooden bench, built by Eagle Scout Will Besgen
Follow the main trail to the north, crossing raised walkways along the way. The bench is located at a trail intersection amongst towering beech trees, near the northern side of the preserve.

6. Firefly Sanctuary (info)
Photo location – Seating area
Follow the trail from Sleepy Hollow Road through the woods, over a few bridges, and up to an open meadow. The seating area is located just inside of a split-rail fence, overlooking the meadow.

7. GreenLink between Irwin Park and Nature Center (info)
Photo location – Bridge with antlers and wood railings
From Irwin Park: use the cross walk at the intersection of Weed and Wahackme to head north on Weed Street. Follow the trail as it cuts into the woods, and you’ll see the iconic bridge.
From the Nature Center: head towards “dinosaur swamp”, crossing a different bridge along the way. Continue heading west towards Weed Street, over a few raised walkways, until you reach the bridge with antlers.


Only current Land Trust members (having made a gift of $50 or more in the last calendar year) are eligible to win prizes. To become a member or renew your membership, visit https://newcanaanlandtrust.org/donate/. If you are unsure of your membership status, send us an email.

Rules at our Preserves:
Please remember that it is all of our responsibilities to protect these special places. Help us keep our preserves open to the public by following the guidelines on this page: https://newcanaanlandtrust.org/all-properties/. Specifically, please adhere to the following rules:

  • Preserves are open from dawn until dusk.
  • Leave what you find so that others may enjoy it (…except litter).
  • Be considerate to other visitors and our neighbors.
  • Leash your dog(s) at all time. Pick up any solid waste and bring it home with you.


  • Participants are encouraged to wear sturdy shoes. While we try to keep our trails in good shape, heavy rain will create some muddy patches, and there are occasional tripping hazards such as roots and rocks.
  • If you come across any hazards on the trails, please let us know so we can address them.
  • Be sure to check out the kiosks at each trailhead for additional information about the preserve.
  • Help spread the word about this challenge by inviting your friends and family to participate.