Dog Friendly Hiking Trails in Westport, CT

There are 22 dog friendly hiking trails within 20 miles of Westport. 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 Westport.

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 now as they were when he lived there. Explore more than 80, dog-friendly acres of forests, salt marshes, and meadows on trails and boardwalks with your pup. Although dogs 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
Pet Friendly Lake Mohegan Open Space
Lake Mohegan Open Space Lake Mohegan Open Space is a beautiful dog-friendly recreation area in Fairfield, CT. The scenic hiking trails take you around the lake, over a foot bridge, and through woodlands at this 170-acre property. Fido can enjoy some off-leash time on your hike after you reach the "100-foot" sign posted on the trail. Please make sure your pets are under voice control at all times and be sure to clean up after them. See Details
Bailey Arboretum BringFido 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. Bailey Arboretum is open to the public, year-round from 9am to 5pm. See their website for current operating schedule. Admission is free, but donations are welcome and encouraged. See Details
Mountain Lakes Park Trail Mountain Lakes Park Trail is an easy, 5.15 mile hike in Mountain Lakes Park that will take about 3 hours to complete with Fido. This gentle trail will give you the opportunity to hike around Westchester County?s highest peak, that stands 982 feet tall. Explore forests and take a break in any or all of 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
Collis P. Huntington State Park Collis P. Huntington State Park is a perfectly tranquil setting in which you can enjoy hiking, canoeing, and pond fishing in five ponds with your pup. Just keep your dog on a leash at all times. See Details
Tarrywile Park Bring Fido out for an afternoon of fun and exploration on the trails at pet-friendly Tarrywile Park in Danbury, CT. Leashed pups are welcome at this scenic park featuring plenty of parking, hiking trails, benches, picnic tables and a pond. See Details
Cold Spring Harbor State Park Cold Spring Harbor State Park is pet-friendly. The park is comprised of 40 acres of hilly terrain that offer scenic vistas of the Cold Spring Harbor. Take your pooch for a walk through mixed hardwood forest on a variety of trails. Leashed pups are welcome, as long as they are cleaned up after. See Details
Ward Pound Ridge Reservation Trail Ward Pound Ridge Reservation Trail is a moderately easy, 7.5 mile hike in Ward Pound Ridge Reservation that will take about 2.5 to 4 hours to complete with Fido. You and your pup will enjoy this easy trail with only a couple of moderate climbs. Your dog will delight in the stream crossings and hiking by your side on the wide road, while you take in the scenic vistas and historical points. Please note that dogs must be leashed; dogs not permitted in picnic areas. 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
Cranbury Park Cranbury Park in Norwalk, CT, is located on the Gallaher Estate and offers some dog-friendly areas on the property for dogs to run off leash. Dogs are also allowed on the trails and in the orchard. Please note that dogs are not permitted on the Great Lawn or near the mansion, playground or pavilion. See Details
Pequonnock River Trail The Pequonnock 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 Monroe! The map below shows a parking area with convenient access to the Pequonnock 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
Pequonnock River Trail The Pequonnock 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 Trumbull! The map below shows a parking area with convenient access to the Pequonnock 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
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
Paugussett State Forest Leashed dogs are welcome at Paugussett State Forest, a pet-friendly recreation area in Sandy Hook and Newtown, CT, that boasts boating, fishing, and hiking opportunities. Pups and their owners who are visiting the park between March and October may want to hit up the popular Zoar Trail, a 6.1-mile loop trail that takes in a number of the sights in the park, including a beautiful waterfall. See Details
Kettletown State Park Leashed dogs are welcome at Kettletown State Park, a pet-friendly natural area in Southbury, CT. Fido can join you in the shaded picnic areas and on the hiking trails throughout this 605-acre park. Please note that pets are not allowed on the beach or in the campground. See Details
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
Mead Memorial Park Pet-friendly Mead Memorial Park welcomes leashed dogs at this favorite neighborhood spot in New Canaan, CT. Featuring a large pond, trails, picnic benches, shaded areas, a seasonal cafe and water fountains, you and Fido are sure to enjoy a great afternoon. See Details
Sunken Meadow State Park Dogs are allowed in undeveloped areas only of Sunken Meadow State Park in Kings Park, NY. Offering one of the most stunning views of the Long Island Sound with Connecticut in the distance, the park has a wide range of topography that sustains a variety of flora and fauna. Dogs must be leashed. Pets are not permitted in playgrounds, buildings, golf courses, boardwalks, pools and spray-grounds or guarded beaches. Sunken Meadow State Park is open daily. See Details
Wooster Cemetery Take Fido for a walk through history at Wooster Cemetery in Danbury, CT. Meander along the paved, dog-friendly paths of a cemetery that has been around since 1850. The land also features a small pond which is popular for local birds. Please leash and clean up after your pets. See Details
Bennett's Pond State Park With more than 450 acres to explore, you and your pup will find plenty of hiking possibilities at Bennett's Pond State Park. Just keep Fido on a leash at all times. See Details
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
Kings Park Bluff Kings Park Bluff is pet-friendly. Bring your leashed pooch to this iconic local hangout for unrivalled views across the serene river and sound. Dog owners are reminded to clean up any mess that is left behind. Kings Park Bluff can be accessed every day of the week from sunrise to sunset. See Details
Rocky Glen State Park Leashed dogs are welcome at Rocky Glen State Park, a pet-friendly, undeveloped natural space located in Sandy Hook, CT. This 46-acre park is home to stunning views of craggy cliffs, old abandoned iron bridges, a river running through the center and numerous side trails for you and Fido to explore. See Details