Family Friendly Hiking & Walking Trails - Newtown Moms

Taking advantage of all of the trails we have in Western CT is a great way to spend a weekend (or really any) morning or afternoon. I published the list below back in April 2020 during the height of COVID and have added a few additional spots to my original list. If you have any other favorite, please email them to me at [email protected]. The original post (view it here) continues to be one of the most sought-after pieces of content on

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).

Catherine Violet Hubbard Animal Sanctuary – Over 34 acres to explore.

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.

Flanders Nature Center, Woodbury: 2,100 acres to explore

Devil’s Den, Weston, CT – 7.8 mile loop

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.

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