Biking and Hiking Trails

During the warmer months, people are often looking for local hiking and biking trails to try with kids – or even solo when the kids are with their grandparents for a weekend! We compiled a list of some of the favorites from this community, but can always add others, so please reach out anytime! Happy trails!

  • Collis P. Huntington State Park (Redding) – great walking/hiking trails with beautiful lake
  • Devil’s Den (Weston/Redding) – walking trails and great bird watching; dog friendly
  • Earthplace (Westport) – great walking trails in warm – or colder – weather, animal exploration, and it’s close!
  • Farmington Canal Heritage Trail (also called the New Haven Rail Trail) – walk, bike, or rollerblade! M&M Fun Fact: For biking, it is recommended to pick the trail up in Hamden (vs New Haven) to avoid the starts and stops of the city! It goes 84 miles all the way to Massachusetts!
  • Gillette Castle (Hartford) – hiking trails. M&M Fun Fact: It is important to know that the castle is only open Memorial Day through Labor Day
  • Lake Mohegan (Fairfield) – hiking trail around the lake where dogs are allowed; great with young kids
  • Norwalk River Valley Trail (Norwalk/Wilton)- hiking trails through 5 towns in CT. M&M Fun Fact: For a 3-4 mile hike (not great for strollers), it is ideal to pick up in Wilton on Rte 7 near Orem’s Diner
  • Pequonnock River Trail (Monroe) – Hiking or biking. There is a flat, relatively easy 5 mile trail that ends at a playground on a little lake. The trail can be picked up in Bridgeport, Monroe, or Trumbull
  • Putnam County Trailway (Putnam, NY) – ideal for biking – starts in Brewster, NY and heads south 12 miles
  • Racebrook Tract (Orange) – hiking trail (GREAT for families), and pick up pizza in New Haven after from Modern, Sally’s, Bar Pizza or Peppe’s!
  • Saugatuck Trail (Weston) – hiking trail; a newish 5-mile trail extension connects the Saugatuck Trail and Aspetuck Trail to provide hikers, joggers, and others a continuous and spectacular 18-mile-long trail system in the heart of Fairfield County.
  • Sherwood Island – a hidden gem for walking or a quiet, beautiful beach morning
  • Sleeping Giant (New Haven) – little further away, but a great, scenic trail!
  • Talcott Mountain Trail (near Simsbury closer to Hartford); nice moderate hiking trails where dogs are allowed on leash
  • Trout Brook Valley Preserve (Weston or Easton) – mainly hiking trails
  • Walnut Beach Boardwalk (Milford) – great for hiking and biking, summer concerts, and more. M&M fun fact: the bike rental place is right on site
  • Weir Farm  (Wilton/Ridgefield) – great walking trail and lots of fun for kids – art, painted bison spotting, and the kids can earn their rangers badge and then there is a really nice family hike to a lake

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