The 10 Best Cross-Country Skiing Trails in Connecticut!

Swoosh, glide, swoosh, glide. Strap on your skis and get ready to take advantage of Connecticut’s winter wonderland by cross-country skiing through pristine nature preserves. Check the weather forecast and wait for fluffy, powdery snow and cold weather, which make the perfect cross-country skiing conditions.

1. Woodbury Ski Area, Woodbury, CT

In addition to downhill skiing and snowboarding, enjoy cross-country trails through wooded areas at the Woodbury Ski Area. Proudly one of the first to open and last to close in the season, Woodbury Ski Area is one of the best options in the state for early or late season cross-country skiing. Please the whole family with a trip to the Woodbury Ski Area, which has something for everyone.

2. Pratt Nature Center, New Milford, CT

Pratt Nature Center is a family-friendly wildlife preserve and education center that is great for hiking, birdwatching, sledding, and cross-country skiing through meadows and woods. The Pratt Center was opened in 1967 as a nature center with education for children and still maintains that focus today. They strive to “let kids be kids,” making this the perfect place for families to teach their children how to cross-country ski and be among nature.

3. Winding Trails Cross Country Ski Center, Farmington, CT

With 12 miles of wide, groomed trails, the Winding Trails Cross Country Ski Center is a popular location for groups of skiers and families. Those without ski gear can rent it from their onsite store, and infant/toddler sleds are also available for rent. The Winding Trails Cross Country Ski Center also has a heated ski lodge and ice skating rink.

4. Waveny Park, New Canaan, CT

Waveny Park features three miles of ungroomed, marked trails through woods and fields that are great for cross-country skiing through beautiful nature. The Waveny House (the town’s municipal building) is in the center of the park and is beautiful from the outside and the inside. Find a sign with a detailed map of the trails and grounds in the field in front of the Waveny House.

5. Air Line State Park Trail, Multiple locations

For wonderful running, hiking, biking, and cross-country skiing spanning Connecticut from New York to Boston, visit the Air Line State Park Trail, which was a former railroad track. Enjoy activities along ungroomed trails that may be flat to a slight incline. The Air Line State Park Trail can be easily reached through several locations across Connecticut including through entrances in East Hampton, Colchester, Thompson, and Putnam.

6. White Memorial Foundation, Litchfield, CT

This environmental education center is packed with activities for all seasons, featuring hiking, snowshoeing, and cross-country skiing in the winter. Ski along 40 different ungroomed trails following one of their maps that can be viewed online or purchased in the on-site store.

7. Housatonic Valley Railbed Trail, Monroe, CT

Cross-country ski, bike, run, hike, or walk your dog at the Housatonic Valley Railbed Trail in Monroe. Ski through parks and along rivers from Monroe all the way into the neighboring towns of Newtown or Trumbull on this out and back trail that is approximately 20 miles long. The trail is ungroomed and mostly flat making it appropriate for all cross-country skiing skill levels.

8. Northwest Park and Nature Preserve, Windsor, CT

Enjoy 12 miles of trails across nearly 500 acres of pristine land at the Northwest Park and Nature Preserve. The park also frequently holds events and concerts for children, families, and adults to inspire and encourage learning about wildlife, climates, and ecosystems. The park is open from dawn until dusk, so plan your cross-country skiing outing accordingly.

9. Chatfield Hollow State Park, Killingworth, CT

At the Chatfield Hollow State Park you can enjoy numerous cross-country skiing trails with loops from less than one mile long to 10 miles long. Come prepared with your own ski gear as this state park, like most other state parks, do not have rental services on-site.

10. Gay City State Park, Bolton, Hebron, and Glastonbury, CT

Ski through beautiful, ungroomed trails, pristine nature, and the crumbling ruins of the former mill town that once thrived at this site. Gay City State Park is massive at 1,569-acre, making this a cross-country skiing site that could be explored throughout the whole season. A detailed trail map can be found on the DEEP website.

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