Dog Friendly Hiking Trails in Port Chester, NY

There are 68 dog-friendly hiking trails within 20 miles of Port Chester. 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 Port Chester.

Sands Point Preserve

Sands Point, NY

Sands Point Preserve Bring Fido to walk along the Sand Point Castle or hike up the cliffs at Sands Point Preserve, overlooking the Long Island Sound in San Points, NY. Fido must be leashed at all times. Dogs are not permitted on the beach at any time. The Dog Run – also known as Charlie’s Run – offers two large spaces for pups to romp and socialize, one for small dogs and one for dogs of any size. See Details

Sagamore Hill National Historic Site

Oyster Bay, NY

Sagamore Hill National Historic Site Theodore Roosevelt loved animals, and dogs are as welcome at Sagamore Hill National Historic Site in Oyster Bay, NY, where he lived. Explore more than 80 dog-friendly acres of forests, salt marshes, and meadows on trails and boardwalks with your pup. Although your furry friend cannot enter any buildings, they are welcome throughout the grounds. There's even a nature trail to the beach, so your pup can dip his toes in the water. Just remember Fido must be leashed at all times. See Details

Ward Pound Ridge Reservation Trail

Pound Ridge, NY

Ward Pound Ridge Reservation Trail Ward Pound Ridge Reservation Trail is a moderately easy, 7.5-mile hike in Pound Ridge, NY. You and your pup will enjoy this pet-friendly path with only a few moderate climbs. Your dog will delight in the stream crossings and hiking by your side on the wide road while you take in scenic vistas and historical points. Please note that dogs must be leashed and are not permitted in picnic areas. See Details

Blue Mountain Reservation

Peekskill, NY

Blue Mountain Reservation Blue Mountain Reservation is a 1,500-acre park in the northwest section of Westchester County in Peekskill, NY. This recreation area offers more than 20 miles of hiking and mountain biking trails. One of their easy, dog-friendly paths will lead you to two ponds and sweeping views of the surrounding countryside. Due to the heavy population of mountain bikers, Fido must be leashed. See Details

Alley Pond Park

Oakland Gardens, NY

Alley Pond Park Alley Pond Park is a dog-friendly spot in the heart of Oakland Gardens, NY. A beautiful hidden secret of NYC, trade the hustle and bustle of the city for miles of well-maintained trails. This area also has an enclosed dog run to exercise Fido and several designated off-leash areas. Please note your furry friend can only be leash free from when the park opens until 9:00 AM and 9:00 PM until closing. See Details

Bailey Arboretum

Locust Valley, NY

Bailey Arboretum Bring Fido on a relaxing stroll through the dog-friendly Bailey Arboretum in Locust Valley, NY. The Arboretum features a charming 18th-century farmhouse and forty-two acres of rare and unique trees. Leashed dogs and their owners can explore marked trails for free. See their website for the current operating schedule. See Details

Mianus River State Park

Stamford, CT

Mianus River State Park Mianus River State Park, formerly the estate of singer and actress, Libby Holman, is a pet-friendly area in Stamford, CT. The river weaves through this 400-acre urban forest where visitors enjoy biking, fishing, hiking and horseback riding in the area. Leashed dogs are welcome as long as they're cleaned up after, but please note that commercial dog walking is not permitted. See Details

Inwood Hill Park Trail

New York, NY

Inwood Hill Park Trail Inwood Hill Park Trail is an easy, 2-mile hike that will take about 1 hour to complete with Fido. Moderate slopes offer you and your pup some exercise as you hike through the only natural park on Manhattan Island. Dogs must be on a leash no longer than 6 feet. See Details

Saxon Woods Park Trail

Harrison, NY

Saxon Woods Park Trail Saxon Woods Park Trail is an easy 2.5-mile hike that will take about 1.25 hours to complete with Fido in Harrison, NY. The southern section of Saxon Woods offers hikers and their pups a gentle pet-friendly walk. Dogs are not allowed in picnic areas and must be leashed at all times. See Details

Piermont Pier

Piermont, NY

Piermont Pier This lovely spot was originally the eastern end of the Erie Railroad. Located in the Village of Piermont, NY, the Piermont Pier is open year-round and is popular with dog walkers, joggers, birders and fishermen. During WWII, it was known as "Last Stop USA" because it served as the embarkation point for troops destined for the European theater. Today the pier offers spectacular views of the Hudson River. See Details

Babcock Preserve

Greenwich, CT

Babcock Preserve The Babcock Preserve is a pet-friendly area in Greenwich, CT, that's open to the public during daylight hours for hiking, walking, jogging, cross-country skiing, nature study, picnicking and horseback riding on designated trails. The 4.1-mile loop features forested land filled with a wide variety of wildlife. Leashed dogs are welcome. See Details

Cold Spring Harbor State Park

Cold Spring Harbor, NY

Cold Spring Harbor State Park Cold Spring Harbor State Park is a pet-friendly spot in New York. The park comprises 40 acres of hilly terrain that offer scenic vistas of the Cold Spring Harbor. Take your pooch for a walk through mixed hardwood forests on various trails. Leashed pups are welcome as long as they are cleaned up after. See Details

Gedney Park

Chappaqua, NY

Gedney Park Discover the wonders of Gedney Park, a delightful pet-friendly recreation area in Chappaqua, NY. This park provides a special treat for your furry companion! During designated morning hours, your pup can happily explore the picturesque trails off-leash, embracing the freedom of nature. At any time of the day, your four-legged friend is welcome to accompany you to the park, joyfully strolling on a leash. See Details

Dog Runs at Van Cortlandt Park

Bronx, NY

Dog Runs at Van Cortlandt Park Van Cortlandt Park in Bronx, NY, has three dog runs where Fido is welcome to explore, socialize and play off-leash. The Canine Court dog run is located on Broadway and 252nd St. Oneida Run is located in the East section between Oneida Ave and E 238th St. The Sackerah Woods Dog Run is located at Gun Hill Rd and Gates Pl. These fenced recreation areas include separate sections for small and large dogs. See Details

North County Trail

Yorktown Heights, NY

North County Trail The North County 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 Yorktown Heights! The map below shows a parking area with convenient access to the North County 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

Bartlett Arboretum & Gardens

Stamford, CT

Bartlett Arboretum & Gardens Bartlett Arboretum & Gardens is pet-friendly. Bring your pooch along to explore 12 miles of garden trails and wander around the Bartlett, a living classroom for people and dogs to experience and enjoy nature. They offer an enchanting environment, where you can explore the grounds with your pup, research a particular variety of plant or attend an event. Their trails will take you through beautiful gardens, past champion trees, and into native Connecticut habitats, alongside colonial stonewalls and over pristine wetlands. Bartlett Arboretum & Gardens is open every day of the week from dawn until dusk. See Details

Rockleigh Woods Sanctuary

Rockleigh, NJ

Rockleigh Woods Sanctuary Check out the pet-friendly Rockleigh Woods Sanctuary in Rockleigh, NJ. This recreation area features more than 200 wooded acres and 4.5 miles of trails. Leashed pups are welcome, but please remember to clean up after them. See Details

Kitchawan Preserve Trail

Ossining, NY

Kitchawan Preserve Trail Kitchawan Preserve Trail is a moderately easy, pet-friendly, 4-mile hike in Ossining, NY. This trail is popular amongst dog owners as the wide path allows you to hike side by side with your pup through the mature forests. Dogs must be on a leash no longer than 6 feet throughout your visit. See Details

Sleepy Hollow Cemetery

Sleepy Hollow, NY

Sleepy Hollow Cemetery The Sleepy Hollow Cemetery is pet friendly. This cemetery in Sleepy Hollow, NY, is the final resting place of Washington Irving, the author of The Legend of Sleepy Hollow. Leashed dogs are welcome to join their owner here if they are cleaned up afterward. Unfortunately, dogs are not welcome on tours of the cemetery. See Details

Rockefeller Preserve Trail

Tarrytown, NY

Rockefeller Preserve Trail Embark on a rewarding adventure with Fido along the captivating Rockefeller Preserve Trail, an 8.25-mile hike within the serene Rockefeller State Park Preserve in Tarrytown, NY. This dog-friendly picturesque path offers a delightful journey through unspoiled forests, meadows and wetlands. It's important to note that leash regulations apply, ensuring a safe and harmonious experience for all visitors and their furry companions. See Details