Dog Friendly Activities in Chestertown, MD

There are 13 dog friendly activities within 20 miles of Chestertown. 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 Chestertown.

Pet Friendly Kent Island Dog Park
Kent Island Dog Park Bring your pet to romp and play off-leash at this Stevensville dog park near hiking trails. See Details
Pet Friendly Matapeake Park Dog Beach
Matapeake Park Dog Beach Matapeake has a public beach with a clubhouse, and a nearby trail that winds around to the dog beach section. The trail itself is a nice short hike for the dog, yet is long enough that it’s adequately separated from the public areas. Dogs can run off leash, retrieve in the water, and sniff out the surroundings. See Details
Cross Island Trail The Cross Island 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 Stevensville! The map below shows a parking area with convenient access to the Cross Island 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
Terrapin Nature Park This hidden gem of a park has unlikely access through an industrial/business area. The entrance is gained off Log Canoe Circle. Park in the parking lot and follow the trail. The trail winds around the 270-acre nature park through woodlands, marsh, and tidal ponds. Take one of the side trails off to the left to get to the beach that runs along the shore of the Chesapeake that allows dogs on a leash. The views of the Bay are great and the surroundings tranquil. The beach isn't huge, but Rover will love the romp. See Details
Adkins Arboretum This 400-acre garden includes miles of paths through woodlands, meadows, and wetlands - a wonderful place for you to explore with your on-leash pet. See Details
Tuckahoe State Park Dogs are welcome at Tuckahoe State Park in Maryland. You can explore the park with your pooch from many different angles on the 20 miles of scenic hiking trails, including the Tuckahoe Valley Trail, a self-guided Natural Trail, the Physical Fitness Trail, and the Lake Trail. The centerpiece of the park is a 60-acre lake, popular among anglers and recreational boat users alike. Additionally, there are two picnic areas that overlook the water and the adjacent woodland. Fido is welcome to join you around the park in the day-use areas and on the trails if they are on a leash and all mess is cleaned up after them. Tuckahoe State Park is open every day of the week from sunrise to sunset. See Details
Aberdeen Dog Park Aberdeen Dog Park is pet-friendly. Dogs are welcome to join their owners at this public recreation area in Aberdeen, Maryland. The fenced park is full of shady trees and grassy spaces to explore with your pooch. Dog owners are reminded to clean up any mess that their pooch leaves behind and to make sure that they are well-behaved during their visit to this park. See Details
Wye Oak State Park Wye Oak State Park is pet-friendly. This 29-acre park was originally set up to preserve a Wye Oak, which unfortunately toppled many years ago. You can wander around the area where it once stood with your pooch. Dogs are welcome on a leash under six feet, as long as all mess is cleaned up after them. Wye Oak State Park is open every day of the week from sunrise to sunset. See Details
Kent Island South Trail The Kent Island South Trail is a multi-use trail that's a great place to walk Fido in Stevensville! The map below shows a trailhead where you can pick up the Kent Island South 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
Abingdon Road Dog Park Abingdon Road Dog Park in Abingdon, MD, invites Fido to enjoy this dog-friendly park with two fenced areas. The 4-acre park features a 1-mile paved trail leading up to the dog park. There is also a pavilion and benches for resting. See Details
Cross Island Trail The Cross Island 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 parking area with convenient access to the Cross Island 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
Hart-Miller Island State Park Hart-Miller Island State Park is dog-friendly. You can bring Fido with you to enjoy the 1,100-acre island on Chesapeake Bay near the mouth of Middle River. Moor your boat on the west side of the island, where you'll discover a 3,000-foot sandy beach. This is the perfect spot for people who are looking to get away from it all to a tranquil, luscious island that can only be accessed by boat. Ornithologists will discover plenty of birds that call the island home. Dogs are welcome on leash under six feet, as long as owners clean up any mess that they leave behind. Hart-Miller Island State Park is open every day of the week from 8am until sunset. See Details
Cult Classic Brewing Cult Classic Brewing is pet-friendly. You can bring Fido with you to enjoy a cold beverage crafted on site. They have lots of beer on tap to explore, including session ale and yam beer. They host events throughout the year that welcome dogs to join in the fun. Food trucks frequent the car park most days during the week and there's a live music room inside, where local bands strut their stuff. Dogs are welcome outside on the limited seating. This brewery and taproom is open every day of the week from 10am to 10pm. See Details