Dog Friendly Hiking Trails in Montgomery, NY

There are 29 dog-friendly hiking trails within 20 miles of Montgomery. 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 Montgomery.

Camp Smith Trail

Cortlandt, NY

Camp Smith Trail Camp Smith Trail is a somewhat difficult 3.5-mile hike in Hudson Highlands State Park in Cortlandt, NY. This pet-friendly trail in the southern part of the park borders the Camp Smith Military Reservation and will take about 3 hours to complete with Fido. Dogs are not allowed in public use areas and must remain on a leash no longer than 10 feet. See Details

Goose Pond Mountain Trail

Chester, NY

Goose Pond Mountain Trail Goose Pond Mountain Trail is a dog-friendly path in Chester, NY. This trail is 5.15 miles long and considered easy in difficulty. Leashed dogs are welcome to join you in exploring the courses in this recreation area, but note that bringing a compass or GPS unit might be wise as some of the trails in this park are unmarked. See Details

Wallkill Valley Rail Trail

Gardiner, NY

Wallkill Valley Rail Trail The Wallkill Valley Rail 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 Gardiner! The map below shows a parking area with convenient access to the Wallkill Valley Rail 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

Doodletown to Dunderberg Trail

Stony Point, NY

Doodletown to Dunderberg Trail Doodletown to Dunderberg Trail in Stony Point, NY, is a difficult 8-mile hike that will take about 5 hours to complete with Fido. This historic trail was used by the British to attack Forts Montgomery and Clinton during the Revolutionary War. You must keep your dog on a leash no longer than 6 feet when hiking this pet-friendly path. See Details

Jones Point Path

Tomkins Cove, NY

Jones Point Path The Jones Point Path is a multi-use trail that's a great place to walk Fido in Tomkins Cove! The map below shows a trailhead where you can pick up the Jones Point Path. 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

Heritage Trail

Goshen, NY

Heritage Trail The Heritage 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 Goshen! The map below shows a parking area with convenient access to the Heritage 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

Long Path Trail

Highland Mills, NY

Long Path Trail The dog-friendly Long Path Trail in Highland Mills, NY, is a challenging, 7-mile hike that will take about 6 hours or overnight to complete with Fido. Only experienced hikers and dogs in appropriate physical condition should attempt this path. Camps can be set up on the mountain near the Hil-Mar Lodge. Leash regulations apply. See Details

Heritage Trail

Chester, NY

Heritage Trail The Heritage 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 Chester! The map below shows a trailhead where you can pick up the Heritage 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

Schunnemunk State Park

New Windsor, NY

Schunnemunk State Park Leashed dogs are welcome at Schunnemunk State Park, a pet-friendly recreation area in New Windsor, NY. Explore the eight marked trails that offer 20 miles of hiking, leading to mountain tops and scenic vistas. Please clean up after Fido and keep him on a six-foot or shorter leash throughout your entire visit. See Details