Dog walking in Cheshire

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

Mary Ellen WCheshire, CT

4.9

(1617)

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Hi, my name is Mary Ellen. I have loved dogs for as long as I can remember and have always had dogs in my family. Dogs are not only a persons best friend but they are also family, and I love them as such. I will treat your dogs as I treat my own, with love and respect and will cater to their specific needs as each dog is different.

Background Checked

High Demand

Top Pet Caregiver

Specialties

Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, Dogs who pull, Puppy care, Potty training

Joshua NCheshire, CT

4.9

(1106)

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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, Fast walker, Dogs who pull, Training experience

Megan HCheshire, CT

4.9

(770)

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Hello! My name is Megan and I just graduated from Georgia Tech with a biomedical engineering degree. I've always loved animals and have been taking care of dogs since I was 10 years old. I have a terrier-mix named Georgia who is 13 years old and still a very energetic pooch. I have over 12 years of experience walking and dog-sitting for all ages and breeds, from pups to seniors with special needs. I can't wait to get to know your dog and take it out to get exercise and explore!

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High Demand

Top Pet Caregiver

Coralys GCheshire, CT

4.9

(504)

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“Your pets new BFF”

Hello! My name is Coralys. Currently I’m an animal care specialist at an animal shelter. I do wag on my free time. I have experience with dogs of all temperaments and sizes. I have a lot of experience with exotics too! I have a passion for animals and I enjoy every moment spent with them.

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

Michael BCheshire, CT

4.9

(593)

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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.

Background Checked

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, Fast walker, Dogs who pull, Puppy care

Samantha BCheshire, CT

4.9

(542)

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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 9 years. I have been around dogs my whole life. I've been walking dogs for 4 years now and have done almost 500 walks. I truly love dogs and always treat them as if they were my own.

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

Marc HCheshire, CT

4.9

(474)

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“I look forward to meeting you and your pups! :)”

Hi there, dog owners! My name is Kylee (please excuse the different profile title, it has to use my legal name). I'm 26 and a college student whose two favorite things are animals and the outdoors. So when I'm walking your dog I'm not just working, I'm having a great time! I was raised with three dogs so I have lots of experience, but I haven't been able to have one of my own since starting school. Feel free to contact me with any questions, I look forward to meeting you and your pups!

Background Checked

High Demand

Top Pet Caregiver

Specialties

Senior dog care, Special needs dog care, High energy dogs, Dogs who pull, Puppy care

Liz CCheshire, CT

4.9

(487)

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Hello, my name is Liz and I have been walking dogs of all sizes for close to 20 years. I am an outdoorsy, active, positive person who enjoys animals of all kinds, particularly dogs.

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, Injected medicine administration, Senior dog care, High energy dogs, Fast walker, Puppy care, Obedience training

Cecile FCheshire, CT

4.9

(443)

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Hey there, I'm Cecile. I learned how to love and care for dogs from my older sisters. Pets have enriched my life. I'd like to, now, be of service to other dog owners. Your pet will be well taken care of, and adored, while in my care. I received my Veterinary Assistant certificate from Middlesex Community College in 2018.

Background Checked

High Demand

Top Pet Caregiver

Specialties

Oral medicine administration, Fast walker, Dogs who pull, Therapy training

Molly SCheshire, CT

4.9

(390)

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“Hi Middletown area! I can’t wait meet your dogs!”

Hi! I’m Molly. I am a former bartender (Covid changed all that) and current Wag walker (I’ve been with Wag for over 2 years). I am new to the Middletown area and am Mom to three rescue cats. I’m a huge animal lover and former dog owner of many years. I have also worked as a vet assistant and am very comfortable around dogs (and cats) of all ages, temperaments, and activity level. I have an open availability at this time. I’m looking forward to meeting as many dogs as possible :)

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

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.