Dog Friendly Hiking Trails in Old Greenwich, CT

There are 49 dog-friendly hiking trails within 20 miles of Old Greenwich. 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 Old Greenwich.

Pet Friendly Sands Point Preserve
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
Pet Friendly Sagamore Hill National Historic Site
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
Sherwood Island State Park Sherwood Island State Park in Westport, CT welcomes leashed dogs in the off-season from October 1st to April 14th. This public recreation area can be found on the shore of Long Island Sound and offers swimming, fishing and dog-friendly trails. Pets are not allowed in the park during the summer season from April 15th through September 30th. See Details
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
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
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 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
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
Mountain Lakes Park Trail Embark on a delightful adventure with Fido along the scenic Mountain Lakes Park Trail, a leisurely 5.15-mile hike within the picturesque Sal J. Prezioso Mountain Lakes Park in North Salem, NY. This hike should take approximately 3 hours of exploration and bonding time with your furry companion and allow you to hike around Westchester County's highest peak, which stands 982 feet tall. Explore forests and take a break in all the gorgeous four lakes. Dogs are not permitted in picnic areas and must be leashed. See Details
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
Belmont Lake State Park Belmont Lake State Park is a pet-friendly spot in West Babloyn, NY. Carll's Creek and Belmont Lake bisect this 463-acre day-use park. Dogs are welcome on the paths that wind around this recreation area. Please note your furry friends aren't allowed in the picnic or playground areas during your visit. See Details
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 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
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 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
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
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
Cranbury Park Located on 227 acres surrounding the historic Gallaher Mansion in Norwalk, CT, Cranbury Park offers some dog-friendly areas on the property for pups to run off leash. Dogs are also allowed on the trails and in the orchard, but they're not permitted on the Great Lawn or near the mansion, playground or pavilion. Please note a parking fee may apply when visiting. See Details
Makamah Nature Preserve Originally called Crab Meadow Park East Watershed, the Makamah Nature Preserve contains dry and wet woodlands, as well as marsh. The preserve is available for hiking, bird watching, dog walking (on leash). It has been reported that 94 species of birds have been recorded in and around the property and that the park is prime habitat for owls and woodpeckers. The park contains heavily wooded hills with one rising to 60 feet in its center and others rising to 100 feet. See Details
Walt Whitman Trail The dog-friendly Walt Whitman Trail is a historic hike at West Hills County Park that will take about 2 hours to complete with Fido in Melville, NY. Aside from the moderate climb to the 400-foot Jaynes Hill, this hike is relatively flat. Horses also frequent this park; you should watch out for them as you hike. See Details
Old Greenwich, CT, US