Where to Go Cross Country Skiing & Snowshoeing in Fairfield County, CT

Places to Snowshoe and Cross Country Ski in Fairfield County, CT

Getting outside this time of year doesn't come naturally -- it can seem far more fun to curl up with cocoa on your couch.  But the kids (and you) NEED to get outside, breathe fresh air and take in some Vitamin D. The trick is finding a fun way to work up a sweat in freezing temps.  Having spent a couple years in Canada as a teen, I can tell you downhill skiing did the trick for me, but in Fairfield County that's obviously not gonna happen.  Instead, you have to get the adrenaline going by strapping on some snowshoes or cross-country skis! 

Here are some places you can test out your skills (or lack thereof), and get a look at local ecosystems through a frosty lens:

New Canaan's Waveny Park is a great place to ski and snowshoe for its simple and free parking, and restroom access inside Waveny House (they just ask you be respectful of the premises).  That being said, there is vehicle traffic running through this town park, so mind your tiny ones closely.  The 3.5 mile course has plenty of woods, and centers around a tudor mansion built in 1912.

677 South Avenue, New Canaan, CT 06840

The tree-lined Ridgefield Rail Trail winds 2.3 miles past the town's open spaces, and was built by CL&P.  Parking is limited to the Prospect St. entrance, and the trail ends at Florida Rd. with a nice, easy downhill ... which means an uphill to get back.  You've been warned!

Parking: Halpin Lane & Prospect St., Ridgefield, CT

The Collis P. Huntington State Park in Redding features open fields, woods and ponds.  There is no cost to park, and the entrance is on Sunset Hill Rd.  Archery deer hunting is allowed from September 15 until December 31, so if you head out in an early snow, wear bright colors and be mindful.

75 Sunset Hill Road, Redding, CT 06896

Housatonic Valley Rail-Trail in Trumbull meanders 3.4 miles along the Pequonneck River.  It is a pleasant, relatively flat course. You'll feel far removed from the hustle and bustle of life here.  Unless you have a town of Trumbull parking sticker, you'll have no choice but to park at the Tait Rd. trailhead (as opposed to the Old Mine Park end).

Parking: Tait Rd., Trumbull, CT

If you're all feeling vigorous and have serious stamina, you can continue from Old Mine Park on to the Housatonic Valley Rail-Trail in Monroe.  This forested course winds through Wolfe Park, and along remnants of one of New England's first railway lines: the Housatonic Railroad.  If you want to originate here, the Monroe trailhead is just a bit off Route 25.

Parking: Wolfe Park, Purdy Hill Rd., Monroe, CT

The Derby Greenway is the first completed phase of what will become the Naugatuck Valley Greenway.  This trail is technically in New Haven County, but this time next year should hook up to Fairfield County in Shelton!  Derby's portion runs just under 2 miles from Division St. to Main St between and along the Naugatuck and Housatonic Rivers.

Parking: Main Street (under the Commodore Hull Bridge, at the train station) or Division Street, Derby, CT

Finally, a little birdie tells Mommy Poppins that snow-under golf courses are a great way to introduce really little ones to the sport.  However, you may want to call management for clearance on this sort of use!

Originally published 1/13/13.


Ridgefield Rail Trail
Halpin Lane & Prospect St
Ridgefield , CT 41° 17' 3.7644" N, 73° 29' 21.282" W
Collis P. Huntington State Park i
75 Sunset Hill Road
Redding , CT
Phone: 203-938-2285
41° 19' 55.5384" N, 73° 21' 35.5032" W
Housatonic Valley Rail-Trail in Trumbull
Tait Rd.
Trumbull , CT 41° 14' 56.8644" N, 73° 12' 7.146" W
Housatonic Valley Rail-Trail in Monroe
Purdy Hill Rd. Wolfe Park
Monroe , CT
Phone: 203-452-3768
41° 18' 25.8228" N, 73° 14' 1.6764" W
Derby Greenway
Main Street under the Commodore Hull Bridge, at the train station
Derby , CT 41° 19' 11.244" N, 73° 5' 8.0556" W