Dog walking in Cheshire

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

Kelly TCheshire, CT

5.0

(335)

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“Providing care, exercise, and friendship!”

My name is Kelly. I live in Meriden, but willing to travel! Animals are my passion. I am an energetic, loving, and experienced petsitter, animal boarder, and dog walker for over 15 yrs. I have over 8 yrs experience with rescue animals. I care for all breeds, from Maltese to Pit Bulls or an English Mastiff! Not just dogs...I care for all pets-cats, birds, fish, reptiles-to name a few! I’d love to meet you and your pets! Your pet is a part of your family, and will care as if they’re mine!

Background Checked

High Demand

Specialties

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

Joshua NCheshire, CT

4.9

(1012)

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“Four legged friends are the best!”

*Woof!* I'm Joshua and I just said 'Hello!' in dog speak. I've been told I'm a good human and often get wet nose kisses in recognition of a job well done. Dogs are simply amazing and I absolutely love them. I appreciate dogs of all sizes and breeds, but big playful pups are my favorite. When caring for your dog, you can rest assured that your fur baby is in the good hands of a trustworthy human who is as loving to your four-legged friend as you are. Your pup is always priority #1!

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

Patrycja LCheshire, CT

4.9

(591)

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“No dog is too big or too small for me”

Hi. My name is Patty. I am an animal lover especially a dog lover. I own a 12 year Aussie-chon and am in open arms when my friends need a sitter for their dog. I have worked at a veterinarian office in the past and i like to better increase my dog and animal knowledge by taking online courses in dog behavior and psychology. I also love physical activity so no dog is too large or too small for me.

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

Michael BCheshire, CT

4.9

(573)

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Hi there, I’m Mike, your local Wag Walker and High School Teacher. I have been caring for all sorts of animals throughout my life. I currently have cats, turtles and a fish. My inLaws have a wonderful dog that a frequently take for walks and play time. I enjoy being around all animals and would love to take your dog for a walk.

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High Demand

Top Pet Caregiver

Socially Distanced Pet Care

Specialties

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

Samantha BCheshire, CT

4.9

(507)

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“I will care for your dog like they were my own!!”

Hi my name is Samantha. I have a pitbull named Rayne who has been my best friend for the last 7 years. I have been around dogs my whole life. I watch my mom and my mother in law's dog anytime they wont be home in time or are going on vacation. I walk my bestfriends dogs when she needs it. I fostered a dog in my home for 3 months. I will always treat your dog like they are my own and will do the best for them!! I'm a huge dog lover and I would love to be able to be friends with your dog!!

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High Demand

Top Pet Caregiver

Specialties

Can run with dogs, High energy dogs, Dogs who pull, Puppy care, Fast walker

Cecile FCheshire, CT

4.9

(433)

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Hey there! I'm Cecile. Growing up I watched my older sisters bring home strays and care for them. I learned from them how to tell if a dog is happy, scared, or in pain. I learned how to calm an anxious dog with a soft voice and that dogs that are more vocal, change their posture, or are not so interested in food, may be in pain or sick. I also learned how much fun it is to play with a dog. I am enrolled in the Veterinary Assistant Program at Middlesex Community College to learn more about the animals I love. I will receive my certificate February 14, 2018.

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High Demand

Top Pet Caregiver

Lydia ACheshire, CT

4.9

(361)

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Hi, my name is Lydia! I've been a dog owner for 18 years, and love spending time with dogs. I have lots of pet sitting experience and I'm excited to get to know your dog!

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Top Pet Caregiver

Kaylee MCheshire, CT

4.9

(316)

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“Your dog will have a paws-itively good time w/ me!”

Hi! My name is Kaylee — AKA your dog’s new friend! I want to help busy pet parents, like myself, feel at ease at work, vacation, or a night out, and to know that their pup is being cared for. When your dog is with me, he/she will be treated like my own — meaning lots of pets, loving, and attention. I have experience with dogs that needs all type of care. I’ll pay extra attention to their needs. I have a dog and a cat, and they’re my world. Thanks for letting me bring that love to your pup!

Background Checked

High Demand

Top Pet Caregiver

Specialties

Special needs dog care, High energy dogs, Puppy care

Ari BCheshire, CT

4.9

(292)

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Hello, I'm Ari. I grew up in New Haven with a bulldog named Mac. I've had a love for animals since i can remember. I have had numerous pets growing up (parrot, rabbit, turtle, fish, cat and a dog) and i started petsitting for friends, family and neighbors at a very young age. I love going for long walks and hikes and i'd love to take your dog with me!

Background Checked

High Demand

Socially Distanced Pet Care

Specialties

Oral medicine administration, Special needs dog care, High energy dogs, Dogs who pull, Fast walker

Sarah LCheshire, CT

4.9

(273)

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I have grown up around all kinds of animals especially dogs both big and small. I currently love and care for a sweet little chihuahua/doxen mix and hope to adopt a larger dog as well. I am very interested in using canine behavior and body language to understand how they feel so I provide the best care possible.

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

Dog Walking in Cheshire

Cheshire is nestled in New Haven County. As a former farming town, it still holds onto a rural atmosphere and strong sense of community. Barns, flowering gardens, mature trees, and historic buildings give it the charm New England towns are famous for. Local dogs love visiting the parks and open spaces, and take comfort knowing that there are four veterinary clinics located right in town.

If you don’t feel like cooking, but don’t want to leave your pup behind, head over to Viron Rondo Osteria for some authentic Italian cuisine. Order the Linguini Vongole or Rigatoni Bolognese then dine al fresco with your pooch at one of the patio tables. For something a bit lighter, try Main Street Café. With steamy soups, refreshing salads, and scrumptious sandwiches, this place will definitely hit the spot. Plus, as long as the weather is nice, your dog can join you at one of the outside tables.

After dinner, take your pup for a stroll around Cheshire Town Park. It spans 75 acres and has sport courts, ball fields, and picnic facilities. However, your pup will be more interested in the trails that wind through the forested area.

No bones about it, Cheshire will make your dog’s tail wag!

Best Dog Neighborhoods in Cheshire

Ives Corner/ Richards Corner

48
Population Density
819 per sq. mi.

Ives Corner/ Richards Corner

48

DeDominics Preserve is the perfect place to spend some quality time with your pup. What was once part of a farm is now a pawsome open space with meadows, hills, streams, and ponds. Leash up your pup and venture out in the preserve. Trails range from .25 to just over a mile, but can be connected to extend your walk. Brooks Preserve is also in the area. A 1.5 mile loop trail foudn here allows you and your four legged hiking buddy to see firsthand the preserve’s natural beauty. Your pup will enjoy views of Mount Sanford and Prospect Ridge while also getting in some much needed exercise. 

Brooksvale Road

36
Population Density
1,138 per sq. mi.

Brooksvale Road

36

You can’t come to Cheshire without visiting the Roaring Brook Park. This gorgeous slice of nature is home to Roaring Brook Falls, one of Connecticut’s longest waterfalls. The falls drop 80 feet over a wooded cliff. Your pooch will love exploring the marshlands and forests that surround the magnificent falls. The Orange Trail runs alongside Roaring Brook. It is steep in places, so make sure your pup is up for the trek. The Quinnipiac Trail cuts through the northern section of the park. This 24 mile trail stretches through several towns in New Haven County, so you’ll have plenty of mileage to walk your pup. 

Mixville/ West Cheshire

24
Population Density
785 per sq. mi.

Mixville/ West Cheshire

24

Next time your pup needs a walk, clip on his leash and head over to Mixville Park. Since it is home to Mixille Pond, a local fishing and swimming hole, this park gets pretty busy during the summer months. Follow the trail around the pond so your pooch can get some much needed exercise. There is also plenty of grassy area for playing and trees for sniffing. Just north of the park is the Mixville Hills Open Space featuring 89 acres that welcomes leashed four legged hikers. The terrain is steep in areas, so your pal will get a pawsome leg workout. 

Honeypot Glen

12
Population Density
923 per sq. mi.

Honeypot Glen

12

This area is home to a furrific park that’s just calling your pup’s name. Snap on her leash and head over to Quinnipiac Park for some fun in the sun. Several sports fields cover a large area of the park, anf if there aren’t any games in play, you can let your pooch gallop across the lawn. Right behind the fields, you’ll find access to the Quinnipiac Park River Walk. The trail cuts through groves of beech, oak, and aspen trees as it runs alongside the Quinnipiac River. Your pal will get a healthy dose of nature as she saunters down the path.  Keep your eyes open for raccoon, deer, and mink. 

Mount Carmel/ Quinnipiac U

0
Population Density
776 per sq. mi.

Mount Carmel/ Quinnipiac U

0

Sleeping Giant State Park is just minutes south of Cheshire in the neighboring town of Hamden. Rolling hills that look like a giant lying on his back give this unique park its name. Your furry BFF will love exploring the network of trails that winds throughout the property. Trails range from just under a mile all the way to five miles, so there is something available for all levels. Be sure to check out the trail that leads to a stone observation tower on top of Mount Carmel. Your pup can look out over the entire New Haven area and see all the way to Long Island Sound.