Dog walking in Chester

Book on demand and scheduled walks with local dog walkers

How it works

Flexible scheduling

Select the date and time that best suit your needs. Want a walk ASAP? We’ve got you covered.

Customized for your pup

Choose between a 20-minute, 30-minute, or 60-minute stroll for your dog.

Follow along

Track your walk with our live GPS tracker, then view your detailed report card after the walk.

What is Wag!?

Wag! is the nation's fastest-growing network of pre-screened and insured pet sitters and dog walkers. In less than 15 minutes you can book a nearby dog sitter, daycare provider, or dog walker, who'll take complete care of your loved one - at their place or yours.

Book walkers near you

Erin JChester, MD

4.9

(468)

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“A house is not a home without four paws.”

Hi there! My name is Erin, and I am a Wag! walker located in Baltimore, MD. I grew up getting to love a pitbull/boxer mix named Megan and a German Shepherd named Sheyna as part of our family. Dogs bring so much happiness to our lives every day. I'd love to return even just a portion of the favor by keeping your fur baby company and taking them for their daily walk!

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High Demand

Top Pet Caregiver

Specialties

Can run with dogs, Oral medicine administration, Senior dog care, Puppy care, Fast walker

Kaitlyn VChester, MD

4.9

(459)

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“Your pup : My passion”

Hi! My name is Kaitlyn. I grew up in Pennsylvania with my best friend, Charlie (a German shepherd). I have experience walking and boarding all sizes and breeds, and I love meeting new dogs. Whether out for a short stroll or a long run, I am so looking forward to getting out and giving your furry family member excellent care and exercise!

Background Checked

High Demand

Top Pet Caregiver

Specialties

Can run with dogs, Oral medicine administration, High energy dogs, Training experience, Dogs who pull, Puppy care

Alina LChester, MD

4.9

(300)

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I am responsible and trustworthy person. I love animals. I have a Boston Terrier. I’ve provided care for dogs and cats of all sizes and ages. When you leave your pets with me, I assure you that they will receive all my attention and love. I am willing to assist you in taking care of your pets when you are away, or if you simply need someone to take your dog on daily walks! I can provide pet sitting and dog walking. I will treat your fur babies like they are my own!

Background Checked

High Demand

Top Pet Caregiver

Socially Distanced Pet Care

Specialties

Dog first aid and/or CPR, Can run with dogs, Oral medicine administration, Senior dog care, High energy dogs, Training experience, Dogs who pull, Puppy care, Fast walker

Shannon GChester, MD

4.9

(243)

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“Puptastic Puppy Pal!”

I really enjoy being a WAG Walker and meeting all of your Furrbabies. I have 25 years of experience rescuing, rehabilitating, training, and caring for all types of animals. Making a new Furrfriend is the highlight of my day and spending time with my old Furrfriends is always fun. If you need me to drop in and take your Furrbaby for a walk, play with them, feed them, give them a bath, take them for a ride to an appointment, or teach them new tricks, I am happy to help.

Background Checked

High Demand

Socially Distanced Pet Care

Specialties

Can run with dogs, Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, High energy dogs, Training experience, Dogs who pull, Puppy care, Fast walker

Trevor PChester, MD

4.9

(195)

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“Always a wonderful wagful walk.”

Hello, my name is Trevor. I have been taking care of dogs, cats and other pets for 16 years. I started taking care of animals when I was 8. My neighbor was unable to walk his dog because of health reasons and I offered to help. Today, 16 years later I have successfully taken care of many different pets. I have taken care of dogs, cats, fish, turtles, rabbits and birds. I have a passion for animals. I believe animals enrich the lives of their owners. It brings me great joy to take care of pets.

Background Checked

High Demand

Specialties

Can run with dogs, Senior dog care, Special needs dog care, High energy dogs, Training experience, Dogs who pull, Puppy care, Fast walker

Sarah SChester, MD

4.9

(153)

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Very experienced dog owner/sitter (over seven years of experience walking dogs and staying overnight). Dog mom to a two-year old rescue named Tippy, whom I raised from the time he was 13 weeks old. College graduate--degree in Biological Sciences. Seven plus years experience working at a pool where dogs come for aquatic exercise, be it for rehab, long term orthopedic issues, or just taking the edge off! Much experience with (and MUCH LOVE for) geriatric dogs! Sensitive and aware of different dogs' temperaments and needs, and able to accommodate effectively any dog. My favorite places to walk dogs are Eastport, downtown Annapolis and Quiet Waters Park, but will be happy to walk in any neighborhood. I work full-time as a server at a restaurant in my neighborhood with a flexible schedule. I have taught my dog and other dogs many "tricks"--I enjoy mental exercise with dogs the same as I enjoy the physical exercise. **CARING FOR YOUR DOG IS MY NUMBER ONE PRIORITY!** Honesty and accountability and doing what I love are what all my values are based on.

Background Checked

High Demand

Top Pet Caregiver

Raechel MChester, MD

4.9

(106)

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Hi. My name is Raechel. I am a very loving and caring person, especially when it comes to my pets and other people’s pets. I love interacting with new animals and getting to know them! When I’m with a dog, it makes walking, running and being outside much more fun and exciting. And I believe it is a great way for me and the doggo to get in some good exercise! I look forward to walking your dog!

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Amy WChester, MD

4.9

(152)

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“Trustworthy Dog Walker”

Hi, my name is Amy and I’m excited to be able to help people walk their dogs! I work as a special education teacher and tutor. I own two dachshunds who are like my children. I enjoy taking my dogs to a park or beach, going to the gym to workout and relaxing on my deck at home! I have always loved animals, especially dogs.

Background Checked

High Demand

Socially Distanced Pet Care

Specialties

Dog first aid and/or CPR, Can run with dogs, Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, High energy dogs, Training experience, Dogs who pull, Puppy care, Fast walker

Caroline HChester, MD

4.9

(115)

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“Pups make life less ruff”

I’ve grown up with animals my whole life and have always loved caring for them. I currently have two bunnies and a hedgehog, as well as a lot of free time and love to give to the wonderful pups in my area. I make my own schedule for work so I’m available often and can work with you on times. The weather is getting more and more beautiful and I’d love to hang outside with your dog while you’re away.

Background Checked

High Demand

Top Pet Caregiver

Specialties

Can run with dogs, Oral medicine administration, Senior dog care, High energy dogs, Dogs who pull, Puppy care

Christina BChester, MD

4.9

(109)

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“Be the person your dog thinks you are.”

I have lived in all different forms of home settings, all around the world, and am familiar with a lot of animals and creatures. I have had dogs nearly my entire life, and have always been around them. I have had my own dog walking service as well as pet sitting service. I am responsible and punctual. I would rather spend my time with animals than humans. :)

Background Checked

High Demand

Top Pet Caregiver

Specialties

Oral medicine administration, Senior dog care, Special needs dog care, High energy dogs, Training experience, Dogs who pull, Puppy care

Dog Walking in Chester

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

Swan Cove Lane

49
Population Density
742 per sq. mi.

Swan Cove Lane

49

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

37
Dog Parks
1 park

Population Density
742 per sq. mi.

Church Street

37

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

24
Population Density
788 per sq. mi.

East Lake Shore

24

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

13
Population Density
3,980 per sq. mi.

Larrimore Point

13

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

0
Dog Parks
1 park

Population Density
6,191 per sq. mi.

Harness Woods

0

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!