Family Friendly Walking & Hiking Trails in Western Connecticut - Newtown Moms

After a somewhat dismal week, I’m happy to report the weather tomorrow is looking gorgeous. And like everyone else, my hope is that as we near the end of April, the weather will continue to improve. Here’s list of places to talk a walk or a hike in Western Connecticut. I’ve included options for strollers, as well as more traditional trails.


Stroller Walks

Fairfield Hills, Newtown: Paved path just under 3 miles running the perimeter of the 185 acre campus.


Housatonic Railway Trail, Monroe: A 3 mile trail with parking located on Cutler Farm Road in Monroe or at Wolfe Park.


Squantz Pond, New Fairfield: Great stroller friendly loop that takes you directly over Squantz Pond for a beautiful view of the park & beyond into Candlewood Lake. In addition, there are also hiking trails at the park.


Rail Trail, Ridgefield: Follows an old rail corridor for about 2 miles from downtown Ridgefield to Branchville. Parking is available on Haplin Lane and at the Ridgefield Playhouse.


Newtown Forest Association, Newtown: NFA protects over 1000 acres of land in Newtown and the oldest private land trust in CT. Holcombe Hill is a favorite in our house. Visit here for a list of protected spaces in Newtown. You may even find something in your neighborhood!


Upper Paugesset State Forest, Newtown: There are two different sections of the forest – The Lower Block (parking on Great Quarter Road) and the Upper Block (Echo Valley Road).


Putnam Memorial State Park, Redding: A few of the trails are paved, which is a nice option if you have a stroller.



Huntington State Park, Redding: Park also borders Bethel & Newtown.



Happy Landings Farm, Brookfield: This preserved space is located right off 25, as you cross into Brookfield from Newtown. It’s a great open space, perfect for exploring while keeping your distance.



Bear Mountain Reservation, Danbury: 140 acres of land, complete with trails. It’s also dog-friendly, so feel free to bring your pup for a hike too!



Tarrywlle Park, Danbury: Four different trails, approximately 3 miles or less



Lovers’ Leap, New Milford: 160 acre state park with hiking trails, scenic views, and historic ruins.



Mine Hill Preserve, Roxbury: Part of the Roxbury Land Trust, this spot offers two different loops that climb through historic mines and quarries.



Steep Rock, Washington Depot: 998 acre preserve offers multiple trails.



Bent of River, Southbury: Trails are open, but center is currently closed. All are welcome to come and explore the 15 miles of trails while practicing social distancing.



Do you have a favorite spot? If it’s open during this time, please email [email protected] to add to the list.

Join The Newtown Moms Community

Stay up-to-date with what is happening in-and-around the Newtown, CT Moms community with local events, community highlights, and exclusive deals.