Dog-Friendly Activities in Chestertown, MD

There’s 1 dog-friendly activity in Chestertown, and 20 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.

Chestertown Farmers Market

Chestertown, MD

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

Ten Eyck Brewing Company

Queenstown, MD

Ten Eyck Brewing Company Ten Eyck Brewing Company is a dog-friendly brewery in Queenstown, MD, where Fido is welcome inside the taproom or outside in the beer garden. The brewery offers a diverse selection of handcrafted, award-winning beers, including foeder-fermented lagers, IPAs, stouts, sours, and ciders. They also produce non-alcoholic sodas and mixed fermentation sour and wild ales. Field Kitchen is sometimes available with food options, and there are occasional guest food trucks for special events. Check their website for an event schedule. See Details

Dog Beach at Matapeake Clubhouse and Beach

Stevensville, MD

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

Stevensville, MD

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

Mariner Point Park

Joppatowne, MD

Mariner Point Park Mariner Point Park in Joppatowne, MD, is a pet-friendly destination offering a variety of outdoor activities for visitors and their canine companions. This hidden gem features paved trails ideal for dog walking, scenic picnic areas, playgrounds and ample space for cycling. The park’s waterfront access makes it a prime location for kayaking, boating and fishing from several piers. See Details

Cross Island Trail

Stevensville, MD

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

Stevensville, MD

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

Tuckahoe State Park

Queen Anne, MD

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

Adkins Arboretum

Ridgely, MD

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

Wye Oak State Park

Wye Mills, MD

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

Kent Island South Trail

Stevensville, MD

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

Cross Island Trail

Chester, MD

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

Eastern Watersports Dundee Creek Rentals

Middle River, MD

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

Eastern Neck National Wildlife Refuge

Rock Hall, MD

Eastern Neck National Wildlife Refuge Rock Hall, MD is home to Eastern Neck National Wildlife Refuge. This dog-friendly area welcomes leashed four-legged friends to explore alongside their owners. Keep an eye out when visiting this 2,285-acre refuge, as you just might see one of the over 240 species that inhabit the land. Owners are responsible for cleaning up after their pets. See Details

Watchtower Brewing Company

Aberdeen, MD

Watchtower Brewing Company Watchtower Brewing in Aberdeen, MD, is a dog-friendly, welcoming 5-barrel brewery and taproom where guests gather to enjoy exceptional craft beer. Located downtown, it serves as a local hub for creativity, camaraderie and craftsmanship. This brewery offers a relaxed atmosphere and stands as a community beacon for both locals and visitors in the heart of the city. See Details

Victory Street Dog Park

Aberdeen, MD

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

Abingdon Road Dog Park

Abingdon, MD

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

Turkey Point Lighthouse

North East, MD

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

Hart-Miller Island State Park

Essex, MD

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

Elk Neck State Park

North East, MD

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