Dog Walkers in Chester, MD

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Dog Areas in Chester, MD

1 Park
1 Trail
2 Eateries

Chester, Maryland is a beautiful bayside town with lots to offer its furry residents and visitors. This town has one park that welcomes dogs, and it’s just a short drive from many other pawesome dog-friendly parks, beaches, and restaurants. If your dog needs a check-up, there’s one veterinary clinic in Chester.

Looking for a great place to take your dog for an on-leash walk? Check out Cross Island Trail! This six-mile trail goes from Stevensville to Kent Narrows, and along the way, it passes through Chester. As you walk along this trail, you’ll go through a beautiful forest, and you’ll also pass by peaceful inlets. Bring doggy bags and water, and have a pawesome time hiking this trail.

If you want to spend the day at the beach with your dog, head to Matapeake Park Dog Beach. Located about six miles from Chester, this beach allows pups to play in the sand and surf off-leash. Here, you and your dog can splash around together in Chesapeake Bay. Or, you can simply relax on the beach and enjoy views of the water. You and your dog will always have a great time here and at the many other dog-friendly attractions in and around Chester!

Best Dog Neighborhoods in Chester, MD

  1. Dog Parks 0
    Population Density 742/sq mi

    #1 Swan Cove Lane


    This Chester neighborhood is home to two waterside attractions you can visit with your pup. If you’d like to take your dog for a walk in the park, head to Ferry Point Park. This 41-acre park is surrounded by three bodies of water: the Chester River, Kent Narrows, and Piney Creek. For great views of all three bodies of water, hop on the park’s mile-long paved trail. After you’re finished at the park, head next door to the Chesapeake Heritage and Visitor Center. Dogs are welcome to join you on the visitor center’s grounds. While you’re here, you can look at the historic items on display, and you can also relax and enjoy views of the water.

    Dog neighborhood?
  2. Dog Parks 1
    Population Density 742/sq mi

    #2 Church Street


    If you’re searching for a pawesome off-leash area for your dog, check out Kent Island Dog Park. This dog park is just two miles from Chester, and it includes separate fenced areas for large and small dogs to play in. Both sides of the park offer fun agility equipment, including ramps, tunnels, and hoops. If all this excitement makes your dog thirsty, water is available. If you want to get a bite to eat with your pup after the dog park, head to Rustico. This restaurant welcomes dogs at their outdoor patio, and they serve classic Southern Italian fare, including pasta dishes, seafood entrees, and veal dishes.

    Dog neighborhood?
  3. Dog Parks 0
    Population Density 788/sq mi

    #3 East Lake Shore


    Lake Shore is home to Downs Park, a furrific place to spend the day with your dog. Located 27 miles from Chester, this park has an off-leash dog beach your pup is sure to love. When you’re at this beach, your dog can enjoy swimming in Chesapeake Bay. Or, you can play games of catch with them in the sand. After your dog is finished swimming, put their leash back on and take them for a walk on one of the park’s numerous woodland hiking trails. Bring water and doggy bags with you, and have a fun day out at this park!

    Dog neighborhood?
  4. Dog Parks 0
    Population Density 3,980/sq mi

    #4 Larrimore Point


    If you want to explore a historical area with your dog, check out Historic London Town and Gardens. This historic site is 23 miles from Chester, and dogs are welcome in all of the gardens and buildings except for the William Brown House. While you’re here, you and your dog can go for walks through the historic area’s 20 acres of gardens. You can also stroll through Colonial-style buildings or take a walk along the South River. If you want a cool treat after your walk, head over to nearby Rita’s Italian Ice. Sit at one of their dog-friendly outdoor tables, and enjoy Italian ices, milkshakes, and soft-serve custard.

    Dog neighborhood?
  5. Dog Parks 1
    Population Density 6,191/sq mi

    #5 Harness Woods


    When you’re in Harness Woods, you won’t want to miss Quiet Waters Park. Located 23 miles from Chester, this park has an off-leash dog run with separate areas for large and small dogs to play in. Quiet Waters Park also has a dog beach where your pup can swim and splash around. If your dog gets thirsty, water is available in the dog park. After the park, continue your fun day out with lunch at Annapolis Smokehouse and Tavern. This barbeque restaurant welcomes dogs at their outdoor tables, and they also serve a special dish just for dogs: kibble with your choice of meat on top. Your dog will love eating here!

    Dog neighborhood?
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