Family-Friendly Hiking Trails in Fairfield County


A family on a hike. During the COVID lockdown, my family increased our hiking expeditions significantly and discovered so many great trails! While we can’t hike as often as we did then, we still love discovering new trails and visiting our favorites. One challenge we had when our babies were too little for hiking packs was finding stroller-friendly trails. I’m happy to report there are a few included here! Did you know there are so many options available to us in Fairfield County?


Bartlett Arboretum and Gardens: Have fun exploring the five miles of hiking trails the Bartlett Arboretum has to offer. Pick up a map at the Visitor’s Center before you head out on the trails. We enjoyed walking the Pond Trail and the boardwalk along the Wetland Walk.

Stamford Museum and Nature Center: Heckscher Farm and the playground are great attractions at the Stamford Nature Center. Also, the Overbrook Nature Center offers miles of hiking trails. There is even a Wheels in the Woods Trail that is universally accessible.

Mianus River Park: A nearly 400-acre urban forest, is sandwiched between Greenwich and Stamford. The trails follow the winding Mianus River. Friends of Mianus River have also created a “Nature Trail in the park with 13 points of interest. The Nature Trail is about two and a half miles long and takes no more than two hours at a leisurely pace.”

Mill River Park: Mill River Park is 30 acres of reclaimed green space in a prime downtown location in Stamford. The paved paths are perfect for strollers, and family-friendly activities, including the playground and carousel, are available. Mill River Park has the largest cherry tree grove in New England and is home to native wildlife.


Cranbury Park: Cranbury Park in Norwalk is perfect when I want to feel like I am getting lost in the woods. This park consists of 227 acres surrounding the historic Gallaher Mansion and offers a series of winding trails that weave in and out of the woods. Although it’s not stroller-friendly, these trails are the perfect place for your budding naturalist to fall in love with the great outdoors. There is also an 18-hole disk golf course.

Norwalk River Valley Trail: This is the longest trail in Fairfield County, 30 miles, spanning through Norwalk, Danbury, Wilton, Ridgefield, and Redding. The trails are family-friendly and include a path along the Norwalk River and various ponds. A section of paved trails in Wilton is perfect for strollers, complete with bridges over streams.


Webb Mountain Discovery Zone: Located in Monroe, admission is FREE! The Webb Mountain Discovery Zone has “Three trails that lead you through an intricate outdoor Scavenger Hunt, created by two of the state’s leading experts, with 27 learning stations featuring interpretive signs that encourage explorers young and old to find clues and evidence of how the land was used by people and animals past and present.”

Wolfe Park: Located in Monroe, Wolfe Park has many attractions, including a stroller-friendly walking path around the pond. The trail is .8 miles and takes about 15 minutes to make one loop. Dogs are not allowed, but fishing is.


New Canaan Nature Center: The New Canaan Nature Center is a botanical garden, arboretum, and nature preserve. We always start at one of the Nature Center’s two observation towers to get a lay of the land. Listening carefully, you can hear the bullfrogs croaking in the marsh below. The New Canaan Nature Center has a 350-foot marsh boardwalk that provides the perfect setting to get up close to marsh wildlife. You can even borrow a net from the Visitors Center and try catching a frog!

New Canaan Land Trust: The Land Trust has around 400 acres of land. Check out the “Places to Explore” tab on the above link, and you will see many options for locations and trails. One of particular interest to explore with young children is the Firefly Sanctuary in Northern New Canaan. In late June and July, visitors are welcome to stay throughout the evening to view fields with thousands of fireflies.

Waveny Park Trails: In addition to a big, open lawn at Waveny Park, there are also easy walking trails that are great for families with kids. There are several trails, each being a little over a mile.


Weir Farm: Weir Farm, located in Wilton, is Connecticut’s only National Park. It is also the only National Park dedicated to American painting. This place is full of art history and naturally provides a beautiful setting for a little nature walk.

Woodcock Nature Center: Free to explore the grounds, the Woodcock Nature Loop is a .9-mile trail with pond views. This is a trail for all ability levels; however, wear your mud boots if it’s rained recently!


Audubon Greenwich: The Audubon Center in Greenwich is a beautiful setting and a great place for families to hike and observe birds and other animals. There are seven nature sanctuaries that are open to the public.

Babcock Preserve: Also located in Greenwich, this is an approximately 4-mile loop in a forest setting. Along the way is an illustrated story for kids, one page at a time, which is great for encouraging little ones to keep moving.


Seth Low Pierrepont State Park: This beautiful state park in Ridgefield is great for hiking. The trails were well-maintained and not too long or difficult for young kids. It was also beautiful with rolling hills, and one of the trails goes around a lake. The town of Ridgefield has great restaurant options for lunch, as everyone is sure to be hungry after a hike.

Hemlock Hills and Pine Mountain Trail: This trail is listed as more difficult, so it may be best suited to families with older children looking for a bit of a challenge and family fun. A lake is situated along the trail, which is approximately 7.6 miles long. The trail is located on one of Ridgefield’s highest points.


Saugatuck Falls Natural Area: Several short trail options are listed on the above link, and many scenic areas to explore Falls Hole at the Saugatuck River with a large cliff.

Huntington State Park: Three trails – white, blue, and green – cross into Bethel or Newtown in parts. The trails are rather level after a descent from the hill entrance. Dogs are allowed on leashes, and horses are often seen traversing the trails. With four ponds and Lake Hopewell, this can easily be a day trip for a family outing. 

Devil’s Den Nature Preserve: Located in Redding and Weston, there are many trails to choose from, with the longest trail taking about three hours to complete. The Nature Conservancy’s largest preserve in Connecticut, it’s a popular location for bird sightings.

Putnam Memorial State Park: Connecticut’s oldest state park was the Continental Army’s 1779 winter encampment. It’s fondly referred to as “Connecticut’s Valley Forge.” This trail is easy; a jogging stroller would be best for the terrain. Remains of the encampment are found on the grounds, including a reconstructed log cabin, canon, and museum with more artifacts. Reenactments are also held here so that you may get a history lesson with your hike!

The Rock Lot/Scott Preserve: A family favorite, the entrance on Secenty Acre provides a choice of trails, Duncan Monro or Joan’s Trail. The highlight on Joan’s trail is “Whaleback,” a large stone feature that resembles a whale. Another feature of this trail is the “Big Oak.” 

Arthur F. Brinckerhoff Preserve: 85.92 acres of open meadow and wooded forest. Enter on Beeholm Road, walk across the “boardwalk,” and you’ll enter a beautiful meadow. There are two trails to choose from, Ensor’s Trace (1.55 mi), which bridges Weston and Redding and connects to Devil’s Den, and Ross’s Ramble (1.7 miles). Both are kid-friendly but not stroller friendly.


Lilinonah Trail: Located in Paugussett State Forest, this 5.9-mile loop is best explored from April through November. With views of the Housatonic River along much of the trail, it’s popular for bird-watching and hiking. This is considered a moderately challenging trail with elevations throughout.

Orchard Hill Nature Center: Looking for a quick, beautiful family-friendly hike? This .8-mile loop off Huntingtown Road takes about 18 minutes to complete and offers views on a bridge over a waterfall and an open meadow. Dogs are permitted on leashes.

Dickinson Park: In addition to an amazing accessible playground, basketball court, and skate park, Dickinson Park has a stroller-friendly walking trail.

Fairfield Hills Campus Walking Trail: If you’re looking for a stroller, dog (on leash), and family-friendly walk, the Fairfield Hills Campus has many options. If you’re up to the challenge, you can take the “big hill” straight to the top of the campus, offering an expansive view of Newtown’s hills. You can also turn left mid-way up the trail and walk through the wildflower fields.


Booth Hill Brook Trail: This trail is great for families looking for an easy hike in the Trumbull area. The trail is approximately 1.6 miles with a river view and is good for all skill levels. Great for some quality family time outdoors with young children.

Do you have a different trail you love? We’d love to know!



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