Chester, MD

Dog walking in Chester

Book on-demand and scheduled walks with local dog walkers. Choose between a 20, 30, or 60-minute walk for your pup.

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Easily find and book trusted Pet Caregivers near you

Pick a service

Whether it's Walks, Drop-Ins, Sittings, or Boardings, choose the service that best fits your pet's needs.

Choose your Caregiver

Select from committed Caregivers who understand your requirements. Chat directly to ensure the perfect match!

Follow along in the app

Download the Wag! App to track walks via GPS, communicate with your Caregiver, and enjoy real-time photo and video updates.

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Customer reviews

Unable to take your dog on a walk today? Dog walkers through Wag! are available to care for your pup whenever you’re not. Every dog walker has passed an enhanced background check. Get photos and updates on where your dog poops and pees while you follow along via GPS in the app.

Abigail P.

Hannah went above and beyond today. She noticed their water jug was empty and filled it before leaving. She's a great pet caregiver!

Abigail P.

Great walker! Very thorough in her comments on my pup s walks.

Darby Driscoll Y.

Thank you!!

Breanna A.

My pup had a bit of a limp from overplaying and Hannah took some extra love and attention.

Erin R.

Thank you, Hannah! I appreciate your walking my difficult senior pups. I am so glad things went well!

Shelley D.

This was Cooper s first dog walk with Hannah and he was so excited for his walk. Hannah was very sweet to him and encouraged his training on a leash.

Erin R.

Thank you!

Michelle H.

Aurora was excellent. She kept me informed on how the pups were doing and paid special attention to my senior dog and shortened his walk. I will request her again.

Mary S.

Aurora was great! She sent videos of our pup during playtime and even gave us a new treat suggestion!

Dae W.

Why book dog walker in Chester

Busy Pet Parents sometimes need a hand when it comes to ensuring their pup is getting the potty breaks and exercise they need. That's where Wag! comes in! Local Chester, MD dog walkers are background checked and registered on the Wag! platform, ready to take your dog on an adventure when you need them. Your dog can make a friend in the neighborhood, and you can re-book with the same dog walker easily in the app. Chester, MD has "pawlenty" of parks and neighborhoods that your dog is itching to explore!

The best dog friendly neighborhoods
in Chester

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.

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.

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!

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.

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!

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Dog walking in Chester

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