Hiking Ideas in Fairfield County - Ridgefield Moms


Taking to the Trails

The woods have always provided a place of comfort and escape from the time I could lace up.  Maybe it is the soothing silence or the soft natural aromas of fir, pine and cedar, time spent in the woods has always left me feeling  spiritually so much better.  It seems au natural to be running to them now during these uncertain and frightening times.  After all, it is maybe the only safe place left to go these days.

Hiking has always been part of my life and now it is a regular part of our families life. We enjoy heading out as a family and introducing the woods to Pippa more and more.  Not only does hiking provide positive physical benefits but the mental benefits that come from just a short time in the woods is unsurpassed.

This past weekend, with the sun shining and spring in the air, we were not the only folks who had the same thoughts. The trailheads were packed with cars, but you know what, there is always plenty of space in the woods.   If you are local to the Fairfield County/ Westchester County area, I wanted to share some of our favorite hikes and nature walks that are within a short drive.   I have briefly described them but attached the links where you can find out more information on your own. I tried to keep the options within 90 minutes.  Hopefully you will find this useful in the weeks to come or down the road.

  1. Ward Pound Ridge Reservation – Pound Ridge, NY

This has always been one of my favorites.  Located in Pound Ridge in Westchester County, the park is quite large and picturesque with 4315 acres.  There are miles upon miles of varied terrain here. Hikes, trail running and in the winter even cross-country skiing take place here.  As a family, we love the Trailside Nature Museum.  It is great for kids to explore the wigwam and explore inside the small nature museum before heading out on the easier yellow trail.  With weather warming it is the perfect spot to pack a picnic lunch. In the summer, camping is allowed.  Due to the large scale size of the park, I would recommend carrying a trail map with you.


2. Mianus River Park – Greenwich, CT / Stamford, CT

The 389 acre nature reserve has entrances both in Greenwich, CT and Stamford, CT.   This park was a favorite of ours when we lived in Greenwich.  This park is great  for walks, trail running and mountain biking. The Mianus River runs through over two miles of the park. We have been known to take breakfast and sit on the large boulders on the banks of the river.  Trails range from flat to moderate.  Pets are welcome.

Access from Greenwich is on Cognewaugh Road and from Stamford on Merriebrook Lane


3. Turkey Mountain – Yorktown Heights, NY

This is a great family hike in northern Westchester County. In fact, this is the hike my husband and his family enjoyed when he was a child.  The climb is 3-mile roundtrip and easy to moderate.  It is a great one with little kids.  Once at the top, there are views of the Croton Reservoir, as well as New York City skyline on a clear day.


4. Devils Den – Weston / Redding, CT – 1756 acres, a very popular hiking destination for those living in Connecticut. Devil’s Den Preserve Trail is a 7.7 mile heavily trafficked loop trail located near Weston, Connecticut that features a lake and is good for all skill levels.



5. Leon Levy Preserve – Lewisboro, NY

Tucked in the corner of NY and Connecticut close to Ridgefield, CT, Vista, NY and New Canaan, CT, just off Rt 123, this is a smaller but great for a shorter hike. With 370 acres there are rock cliffs and wetlands both.



6. Breakneck Ridge – Cold Spring, NY

Located a little over an hour from New Canaan, CT, Breakneck Ridge is located along the Hudson River near the town of Cold Spring, NY.  It is definitely a more challenging hike than most of the others mentioned here. The climb consists of  short but steep inclines with stunning views of the Hudson River. There is some rock scrambling and proper hiking gear is recommended.  Probably not the hike we would take Pippa on right now, but I think older kids would enjoy the challenge!



7. Rockefeller State Park –  125 Phelps Way, Pleasantville, NY

Situated on the former country estate of John D. Rockefeller, there are over 45 miles of scenic carriage roads to explore. I have always loved the trail running here and their peony festival in the spring. The bucolic setting offers a variety of scenes and terrain.  One will pass by historic structures, bridges, sweeping views of the Hudson, grazing cows and farms and beautiful ponds with swans.  If you have some time, go get lost of the beautiful trails we in the running community refer to as ” Rockies”.


8. Mohonk Preserve – New Paltz, NY

Just 90 minutes away, this is a fantastic day trip!  This was where Matt and I went on our first date ever, so it will always be special to us.   Located on the Shawangunk Ridge in Ulster County the scenery is just splendid.  With many trails to choose from, there are plenty, there is a little something for everyone.  If you want a little more challenge, try the Labyrinth & Lemon Squeeze.  Their site here lists some great options.  If you have time, stick around and visit the Mohonk Mountain House and visit their spa and have some lunch.


Below are some other smaller local popular trails that we love and offer a nice ‘get outside’ option for families.

Waveny Park, New Canaan, CT

Greenwich Audoban, Greenwich, CT (* these are however temporarily closed until the end of the month.)

Babcock Reserve, Greenwich, CT

Tod’s Point, Greenwich, CT – the interior trails

These are just a few of the many wonderful natural escapes we have in our area.  There really are so many.   Nature just makes everything feel better!  Be sure to comment below if you have any local hikes you love.

Join The Ridgefield Moms Network Community

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