Dog Friendly Hiking Trails in Westport, CT

There are 19 dog friendly hiking trail 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 The Cascades at Lake Mohegan
The Cascades at Lake Mohegan This is a beautiful dog-friendly recreation area in Fairfield, Connecticut. The trails surround a lake and waterfall/creek called the cascades on acreage donated by the G.E. corporation. There are waste bins for doggie cleanups, so bring your baggies. See Details
Pet Friendly Housatonic Rail-Trail - Trumbull (Pequannock Valley Greenway)
Housatonic Rail-Trail - Trumbull (Pequannock Valley Greenway) The Housatonic Rail-Trail - Trumbull (Pequannock Valley Greenway) 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 Housatonic Rail-Trail - Trumbull (Pequannock Valley Greenway). 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
Sagamore Hill National Historic Site Theodore Roosevelt loved animals, and dogs are as welcome at Sagamore Hill now as they were when he lived there. Explore more than 80 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 that dogs must be leashed at all times. 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
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
Cranbury Park Large Estate (Gallaher Estate) that has an open area in the back of the property for dogs to run off-leash. No fee for residents otherwise $5, which is unusual as most of the parks in NY/CT require you to be a resident and/or pay a fee to enter. Dogs are welcome on the trails that run throughout the property either on or off-leash at the dog owners discretion and ability to control the dog. There are areas of the estate, Great Lawn or near the mansion, playground or pavilion, that are not permitted to have your dog on so be diligent about knowing that as the rules are very strict. There is a park attendant that drives around to make sure you are compliant and he is no-nonsense!. Overall it is a very pleasant place to take your doggie. See Details
Kettletown State Park Pets on a leash are permitted in the picnic areas and hiking trails at this 605 acre state park. Pets are not allowed on the beach or in the campground. See Details
Housatonic Valley Rail-Trail - Monroe The Housatonic Valley Rail-Trail - Monroe 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 Housatonic Valley Rail-Trail - Monroe. 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
Babcock Preserve The Babcock Preserve is 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
Bailey Arboretum BringFido on a relaxing stroll through Bailey Arboretum. 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
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 Excellent trails for a family walk with the dog- nothing steep or strenuous, several loops to add variety. See Details
Sunken Meadow State Park Dogs are allowed in undeveloped areas only of Sunken Meadow State Park. 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 every day of the week from 9am to 8pm. 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
Paugussett State Forest Paugussett State Forest is a dog-friendly recreation area that boasts boating, fishing, and hiking opportunities. Dogs 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
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
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
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