Dog walking in Chester

Book on demand and scheduled walks with local dog walkers

How it works

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Flexible scheduling

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

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Customized for your pup

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

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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

Erica WChester, NY 10918

5.0

(159)

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Hi everyone! My name is Erica. I'm 23 years old and a doctoral student right now getting my degree in physical therapy. Let's see, other interests....I'm a personal trainer, I love to cook and bake, and I watch entirely too many movies.I'm super active and love being outside. If your dogs want to run instead of walk, I'd be more than happy to go on jogs with them. If not, a nice leisurely stroll is perfect. I really hope to get to meet your lovely dogs soon!

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Eddie HChester, NY 10918

4.9

(560)

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Hi my name is Eddie .l would like very much to walk and care for your pup! I have owned and cared for many different breeds. I will care for your dog as if it were my own.

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Specialties

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

Raymond SChester, NY 10918

4.9

(494)

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When I was young I always hanged around dogs I didn't know. I was short in height and the dogs were bigger than me but they all walked around with me with no leash even though I didn't know them they were my furry friends. If the dog wants to walk left I go left if the dog wants to make a right turn I will go right. I'm here to let the dog have as much fun as possible and be as safe as possible. If the dog is lonely I will take away that loneliness by giving the dog plenty attention.

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Cameron WChester, NY 10918

4.9

(296)

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From dogs and cats to reptiles and arachnids, I have been an animal lover since the day I was born! I have owned and nannied K9s that are perfectly-behaved, as well as some that were food and dog aggressive. I would love to take care of your furry friend!

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Joseph RChester, NY 10918

4.9

(202)

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“Dogs are family! :)”

Hi, Wonderful Dog Parents! My name is Joseph, a current college student in Chicago and I have been passionate about pet care ever since I got my own dog. This began not only a great love for dogs, but a hobby to take care of others! My dog care experience has played a major role in my life, specifically working with a variety of dogs and places like New York and Chicago for six years. This involves running, long cold walks, and lots of play time! I hope to be the best pet care provider for you!

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Specialties

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

Katrina PChester, NY 10918

4.9

(201)

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Hi! My name is Katrina. I've been a professional dog walker for 2 years now. I am very versatile in that, I am able to handle dogs of all shapes, sizes, and personalities. I am also a big believer in creating a close bond with every dog I walk. They become like family to me, and if I were lucky enough to walk your dog, you could be sure they would get the same care and love that I would give my own!

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Vanessa FChester, NY 10918

4.9

(192)

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Hello! I am originally from New York and I have worked with animals for over 10 years. I have experience working in a veterinary hospital, a doggie daycare/hotel and am currently working as a dog groomer! I love dogs of all sizes and breeds.

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Specialties

Oral medicine administration, Fast walker

Stephanie AChester, NY 10918

4.9

(181)

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Hi I'm Steph and cannot wait to meet your best friend! I am an extremely personable, upbeat yet disciplined dog walker. As an Exercise Physiologist by trade I enjoy anything active and am willing to push your dog distance, intensity, training etc. I am more than willing to work with you and your dog individually on any specific commands, training or bad habits they may have. Positive reinforcement and communication is key, let me make both of your lives better!

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*Melissa L. GChester, NY 10918

4.9

(161)

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Bubbly walker here! Lover of pets in general, but dogs rule my world. I have volunteered in pet shelters as well as rescued and owned dogs! Currently an obsessive parent of a rescued pitbull. Looking forward to daily adventures with your baby.

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Danielle AChester, NY 10918

4.8

(170)

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Hi Everyone! I grew up with all types of animals and currently have a few myself! I am a full time teacher and full time pet lover!! I’ve been walking and boarding dogs in my home for 4 years and have great references! Can’t wait to meet your fur baby!

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Specialties

Can run with dogs, Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, High energy dogs, Fast walker, Puppy care, Puppy training

Dog Walking in Chester

Chester is a quaint little town in Orange County, New York. Though there aren't many dog-friendly amenities here, Chester is a pawesome place to stay if you're travelling with your furry friend.

If you need a place to stay in Chester, check out the city's AirBnB options. Most AirBnB hosts don't charge extra fees for canine tenants, although pet policies will vary based on the host.

While you are in Chester, you have to visit the Rushing Duck Brewing Company. This brewery is a small family owned and operated business. The Rushing Duck Brewing Company is situated in the Historic District of Chester. They started selling beer in August of 2012. The great thing about this brewery is that they are so dog-friendly that they even allow dogs in the tasting room! Yep, that's right! Beer and dogs -- sounds like heaven to us!

The only rules that you have to follow if you want to bring your four-legged friend here are that your dog is well-behaved and on-leash at all times. Also, you have to know that the brewery has its own pet: a cat named James that often visits the tasting room! If your dog doesn't play well with kitties, you might want to skip this experience.

Best Dog Neighborhoods in Chester

Goosepond Park

48
Population Density
372 per sq. mi.

Goosepond Park

48

The Goosepond Mountain State Park is a 1,706-acre undeveloped park in Chester where you can find a very nice dog-friendly trail called Goose Pond Mountain Trail. The trail is 5.15 miles long, and you can reach the end of the trail in approximately 3 hours. The only problem with this trail is that the territory is unmarked and it is very easy to get lost. Take a map or a use GPS for safety reasons. Even though you can take your fur baby with you, he must be on-leash at all times, and the leash has to be no longer than 6 feet. You should bring lots of water for you and your pup and waste bags to clean up after your dog.

Monroe

36
Population Density
2,498 per sq. mi.

Monroe

36

Here, you'll find the Orange Heritage Trail, which starts in Monroe and finishes all the way over in Middletown, NY. This lengthy trail is 12 miles long and 10 feet wide. The trail is multipurpose; people hike, ride bicycles, and rollerblade here, so keep that in mind. You can bring your dog along, but he has to be on-leash at all times. The trail passes through wildlife sanctuaries, historic landmarks, streams, communities, and meadows. It's a unique experience for you and your pup! You should be prepared if you're planning on finishing the whole trail, though. Bring lots of water, snacks for your pup and yourself, and of course waste bags so you can clean up after your doggo.

Central West Milford

24
Dog Parks
1 park

Population Density
344 per sq. mi.

Central West Milford

24

Waiting for you just 20 miles away from Chester, in central West Milford, is a unique experience. The Pequannock Feed and Pet Supply store has its own dog park: the West Milford Dog Park. This fenced, off-leash park spans one acre and is open during the store's normal operating hours. It has separate areas for small and large dogs and separate entrances as well. There is a parking lot and water available. Moreover, the park offers some agility equipment so your pup can have extra fun. The fence is approximately 6 feet tall and is very secure. The park is free, but the store owner accepts donations to help maintain the park.

Eastern Cornwall

12
Population Density
458 per sq. mi.

Eastern Cornwall

12

Around 18 miles east of Chester is the Storm King State Park. The hiking trail here is pretty difficult to complete, even though it's just 3.5 miles long. It would take you around three hours to complete it along with your pup. Your dog must be on-leash and is not allowed in the picnic areas. The hike offers incredible views of the Hudson River, Bannerman Island, Cold Spring, and Constitution Marsh. Make sure you bring plenty of water and snacks for your four-legged baby. You should also bring a camera for an awesome photoshoot with your best fur-iend!

Montebello

0
Dog Parks
1 park

Population Density
270 per sq. mi.

Montebello

0

Approximately 27 miles away from Chester, in Montebello, you can find the Suffern Kakiat Park, which includes an enclosed dog park. You can let your pup run free there, since it's an off-leash park. There is a parking nearby as well as plenty of shade trees for your convenience. Benches are also available for the humans. The park has plenty of toys and water bowls for your pooch. Aggressive dogs are not allowed in the park. The park is properly fenced and has waste stations to dispose of those poo bags. There are restrooms and picnic tables in the park, as well as hiking trails outside of the fenced area.