Dog Friendly Activities in Chestertown, MD

There’s 1 dog friendly activity in Chestertown, and 16 more nearby. 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 Chestertown Farmers Market
Chestertown Farmers Market Every Saturday, year-round, this market features artisan products from local vendors. Browse the booths of Maryland produce, art, crafts and more. Fido is welcome to tag along on the weekend adventure, but dogs must be well-behaved and kept on a leash. See Details
Pet Friendly Dog Beach at Matapeake Clubhouse and Beach
Dog Beach at Matapeake Clubhouse and Beach The Dog Beach at Matapeake Clubhouse and Beach in Stevensville, MD features a winding natural surface trail through the woods that ends at the sandy banks of Chesapeake Bay. The trail is a nice short hike for pooches, 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 at this pet-friendly designated beach area. See Details
Island Dog Park Bring your pet to romp and play off leash at Island Dog Park in Stevensville, MD. This dog park offers separate sections for large and small pups as well as benches, picnic tables and a water fountain. The large dog area also features agility equipment for Fido to enjoy. 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
Abingdon Road Dog Park Abingdon Road Dog Park in Abingdon, MD, invites Fido to enjoy 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
Victory Street Dog Park Bring Fido to Victory Street Dog Park in Aberdeen, MD for some off-leash exercise and socialization with other pups. This park is full of shady trees and grassy spaces to explore with your pooch. Dog owners are reminded to clean up after their pets during their visit. Street parking is available. See Details
Adkins Arboretum Adkins Arboretum is a 400-acre garden in Ridgely, MD. Enjoy miles of scenic paths through woodlands, meadows and wetlands with your leashed pup. Visitors must remain on the walking paths, and remember to clean up after your pets. See Details
Tuckahoe State Park Fido is invited to spend the day exploring Tuckahoe State Park in Queen Anne, MD. Hike with your pooch on the 20 miles of pet-friendly hiking trails, or relax at a picnic area overlooking the water and adjacent woodland. The centerpiece of the park is a 60-acre lake, popular among anglers and recreational boat users alike. Leashed dogs are welcome to join you around the park in the day-use areas and on the trails. See Details
Wye Oak State Park Wye Oak State Park is a pet-friendly destination in Wye Mills, MD. 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. See Details
Terrapin Nature Park Terrapin Nature Park is a hidden gem with unlikely access through an industrial/business area in Stevensville, MD. This pet-friendly park features a 3.25-mile trail that meanders around the 276-acre nature park through woodlands, marsh and tidal ponds.Take one of the side trails to get to the beach that runs along the shore of the Chesapeake, where dogs are allowed on a leash. 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
Turkey Point Lighthouse Turkey Point Lighthouse is a pet-friendly seasonal attraction in North East, MD. Your leashed pup is welcome to join you for a brisk walk up the lighthouse, where a water bowl will await them. Upon arrival, you'll have breathing views of the Chesapeake Bay. Their operating season is held from May through October. 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 Accessible by personal boat or watercraft only, Hart-Miller Island State Park is a dog-friendly destination in Essex, MD. 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. Dogs are welcome on leash under six feet, as long as owners clean up any mess that they leave behind. See Details
Eastern Watersports Dundee Creek Rentals Eastern Watersports Dundee Creek Rentals in Middle River, MD is dog friendly. Take Fido for an adventure on the water by renting a kayak or stand up paddleboard which is suitable for your canine companion. Lifejackets for humans and dogs are available to rent, or visitors can bring their own. See Details
Queenstown Premium Outlets Fido can come shopping with you at the pet-friendly Queenstown Premium Outlets in Queenstown, MD. This outdoor mall has over 60 designer and name brand stores selling women and children apparel, shoes, and accessories. There are also multiple dining options with outdoor, dog-friendly seating. Well-behaved, leashed dogs are welcome in the common areas, but remember to ask staff at each store before bringing Fido inside. See Details
Elk Neck State Park North East, MD is home to the dog-friendly Elk Neck State Park. This outdoor recreation area invites owners and their canine companions to adventure together and enjoy the waterview. While pets are welcome in the campgrounds, they aren't permitted in the Bohemia, Chester, Tred Avon, Sassafras loops, rustic cabins, or the youth group camping area. Dogs are allowed in all day-use areas as well as the beach area, except for the sandy portion of the swimming beach area from Memorial Day weekend to after Labor Day. See Details
Chestertown, MD, US