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    Dog Friendly Hiking Trails in Cheshire, CT

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    There’s 1 dog-friendly hiking trail in Cheshire, and 41 more nearby. Use the links below to get an overview of each one, see pictures, print directions, and even read reviews from other dog owners. Coming from out of town? Get a discounted rate on pet friendly hotels in Cheshire.

    Pet Friendly East Shore Park

    East Shore Park

    New Haven, CT
    East Shore Park Leashed dogs are welcome at East Shore Park, a pet-friendly recreation space in New Haven, CT. You and Fido can enjoy the meandering walking trail along New Haven harbor. There is also a beach and two fenced areas for dogs to enjoy some off-leash exercise. See Details
    Pet Friendly Silver Sands State Park

    Silver Sands State Park

    Milford, CT
    Silver Sands State Park Leashed dogs are allowed in the pet-friendly picnic areas near the parking lot of Silver Sands State Park in Milford, CT. While the park's biggest draw is the shoreline, unfortunately pets are not permitted on the beach or the boardwalks that lead to the sand. See Details

    Black Rock State Park

    Watertown, CT
    Black Rock State Park Set amongst the scenic rolling hills of the Western Highlands is dog-friendly Black Rock State Park in Watertown, CT. Fido is welcome to join you in the park, but pets must be leashed at all times. Enjoy scenic views, fishing, hiking and picnicking with your best friend by your side. Please note that pets aren't allowed on the beach or in the campground. See Details

    Sessions Woods WMA

    Burlington, CT
    Sessions Woods WMA Sessions Woods WMA is a pet-friendly recreational area in Burlington, CT. There are 5 different trails to hike while enjoying the scenery and wildlife. Fido is welcome to join you on the trails as long as he is leashed and cleaned up after. Dog owners are advised to be mindful of bears and ticks in the area. See Details

    Anchor Beach

    Milford, CT
    Anchor Beach Anchor Beach in Milford has a dog-friendly shoreline walk with gorgeous views and breezes. Please note that Fido isn't allowed on the actual beach, but is permitted on the walk. See Details

    Timberlands

    Guilford, CT
    Timberlands Timberlands, also known as Timberland Preserve, is a dog-friendly hiking area in Guilford, CT. Immerse yourself in a peaceful oasis while you hike through this scenic 588-acre natural area. The trails are mostly level with a few steep grades, and you'll find a stream and lake for Fido to swim in. This area is open for hiking, biking, equestrian use & cross-country skiing. See Details

    Rockland Preserve

    Madison, CT
    Rockland Preserve Leashed dogs are welcome at Rockland Preserve, a pet-friendly outdoor space in Madison, CT. You can Fido can explore the rocky hills, gray cliffs, ledges, and expansive forested areas or hike along the long abandoned ancient trails. Be sure to make your way to the centerpiece of the preserve, Coan Pond, where you may spot rare flowers and native wildlife. See Details

    Branford Trolley Trail

    Branford, CT
    Branford Trolley Trail The Branford Trolley Trail near Branford, CT is dog friendly and one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Branford! The map below shows a parking area with convenient access to the Branford Trolley Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    Webb Mountain Discovery Zone

    Monroe, CT
    Webb Mountain Discovery Zone Leashed dogs are welcome at Webb Mountain Discovery Zone, a pet-friendly outdoor learning center in Monroe, CT. Geared towards educating and exciting children about the wonders of nature, this family-friendly activity offers birding opportunities, a guided scavenger hunt and numerous trails to opt for either a short walk or long hike through the woods with Fido. See Details

    Larkin State Park Trail

    Oxford, CT
    Larkin State Park Trail The Larkin State Park Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Oxford! The map below shows a parking area with convenient access to the Larkin State Park Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    Larkin State Park Trail

    Middlebury, CT
    Larkin State Park Trail The Larkin State Park Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Middlebury! The map below shows a parking area with convenient access to the Larkin State Park Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    Farmington River Trail

    Unionville, CT
    Farmington River Trail The Farmington River Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Unionville! The map below shows a parking area with convenient access to the Farmington River Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    Farmington River Trail

    Burlington, CT
    Farmington River Trail The Farmington River Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Burlington! The map below shows a parking area with convenient access to the Farmington River Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com. See Details

    Naugatuck State Forest

    Naugatuck, CT
    Naugatuck State Forest Naugatuck State Forest covers 5,000 acres of and is split into different blocks in Connecticut. This pet-friendly hikers' paradise has numerous trails that span a variety of terrains. Leashed dogs are come to join you on the trails. See Details

    Mattatuck State Forest

    Thomaston, CT
    Mattatuck State Forest Leashed dogs are allowed at Mattatuck State Forest in Thomaston, CT, where you will find numerous pet-friendly trails. You and Fido will enjoy the waterfalls and overlooks that take in the surrounding scenery. There are numerous access points to this expansive forest, with access via Black Rock State Park being one of the most direct. See Details

    Nassahegon State Forest

    Burlington, CT
    Nassahegon State Forest Leashed dogs are welcome at Nassahegon State Forest, a dog-friendly outdoor space in Burlington, CT. This park is home to a number of different wooded hikes that you and your pooch can attempt together. The Sessions Woods Wildlife Management Area Trail is a picturesque wooded trail that's a big hit among dog walkers. See Details

    Humaston Brook State Park

    Litchfield, CT
    Humaston Brook State Park Enjoy hiking and fishing with Fido at dog-friendly Humaston Brook State Park near Northfield and Litchfield, CT. This 141-acre recreational area welcomes your leashed pup to hike with you on the trails surrounding Northfield Pond. See Details

    Whittemore Glen State Park

    Naugatuck, CT
    Whittemore Glen State Park Leashed pets are permitted to visit Whittemore Glen State Park in Naugatuck, CT. This 242-acre recreation area boasts a variety of dog-friendly hiking trails that furry friends can explore with their owners. See Details

    Indian Well State Park

    Shelton, CT
    Indian Well State Park Leashed dogs are welcome during the off-season, beginning after Labor Day until Memorial Day weekend, at Indian Well State Park in Shelton, CT. Fido is also invited to enjoy the Maples area with you throughout the year, but it's recommended to call the park in advance before visiting with your pup. Popular activities include hiking, picnicking and boating. See Details

    Lamentation Mountain State Park

    Berlin, CT
    Lamentation Mountain State Park Lamentation Mountain State Park is a dog-friendly recreation area in Berlin, CT. Fido is welcome to join you for a hike at this 47-acre park, where you can enjoy some exercise and scenic vistas as you explore with your leashed pup. See Details
    Cheshire, CT, US