Dog walking in Middlebury

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

Kelly TMiddlebury, CT

5.0

(336)

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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!

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High Demand

Specialties

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

Patrycja LMiddlebury, CT

4.9

(626)

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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.

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High Demand

Top Pet Caregiver

Specialties

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

Laura SMiddlebury, CT

4.9

(628)

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“Lots of love to give!”

I have been working with dogs since I was 15, at a local boarding facility. The last 2.5yrs pet care has been my full time job. I've been doing both dog walking, and pet sitting in my home. I love spending time with dogs and bonding with them.

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High Demand

Top Pet Caregiver

Specialties

Oral medicine administration, High energy dogs, Puppy care

Samantha BMiddlebury, CT

4.9

(511)

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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 8 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.

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High Demand

Top Pet Caregiver

Specialties

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

Cecile FMiddlebury, 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

Marc HMiddlebury, CT

4.9

(397)

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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

Devorah LMiddlebury, CT

4.9

(324)

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Hi, I'm Devorah! I love dogs, hiking and just being outdoors - no matter the weather. I've been petsitting for ten years for several happy, repeat customers, but I would like more clients. I currently regularly sit-for/walk three pitbull-mixes that I adore. I love to bring them to hiking trails where we can travel by pack.

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High Demand

Top Pet Caregiver

Kaylee MMiddlebury, 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!

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High Demand

Top Pet Caregiver

Specialties

Special needs dog care, High energy dogs, Puppy care

Ari BMiddlebury, CT

4.9

(293)

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Hello, I'm Ari. I’ve been walking dogs since i was a kid and have been using wag for about 3 years now. I love going for long walks and hikes and i'd love to take your dog with me!

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High Demand

Socially Distanced Pet Care

Specialties

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

Rosika BMiddlebury, CT

4.9

(283)

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Hello...My name is Rose and I’m happy to introduce myself. All my life I had the pleasure to spend with dogs since I was 4 years old. From Great Danes to Jack Russell’s. My best friends are my 2 German Shepherds. And I believe that all dogs should be a priority to make sure that they are taken care of and happy. I would love to be your helping hand to care of your dog.

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Top Pet Caregiver

Dog Walking in Middlebury

New Haven County is the third-most populous county in Connecticut, and in addition to big cities like New Haven and Waterford, it's also home to a town called Middlebury. More than 7,000 people live in Middlebury, and the town is known for being a wonderful place to raise a family. Many people choose to live in Middlebury and enjoy its charming small-town feel while traveling to nearby cities each day for work. Not only are there great schools in Middlebury, but there's also an excellent parks and recreation system in town, as well as a variety of restaurants, shops, and businesses. Luckily, there are dog-friendly activities in and around Middlebury to keep you and your four-legged companion busy!

You and Skip won't want to miss Blarney Stone Pizza on Middlebury Road. This casual pizza restaurant has several outdoor tables, and your dog can join you for a meal outside when the weather is nice. Blarney Stone Pizza serves all sorts of pizzas, as well as calzones, sandwiches, soups, sandwiches, appetizers like mac and cheese bites and mozzarella sticks, and several desserts. If you can't make it into Blarney Stone Pizza, they also deliver! Once you're done with your meal, you and your pooch can head to a nearby dog park or trail for a day of fun.

Best Dog Neighborhoods in Middlebury

Northeast Middlebury

48
Population Density
588 per sq. mi.

Northeast Middlebury

48

You can access the Middlebury Greenway Trail in northeastern Middlebury. This 4.5-mile asphalt trail is ideal for dog walking, inline skating, cycling, and jogging, or cross-country skiing in the winter. This trail is one of 1,600 trails that stretch across the United States, and each one was built from an abandoned railway line. This trail spans the whole town, and you'll get to know Middlebury well during your walk. You'll come across businesses and parks, and the trail ends at an amusement park that's been around for more than 100 years. Near the amusement park, there's also a swimming lake. Be sure to keep your dog on a leash on this trail!

Heritage Village

36
Dog Parks
1 park

Population Density
1,125 per sq. mi.

Heritage Village

36

When it's time to enjoy an off-leash activity with your dog near Middlebury, the two of you can make the ten-minute drive to northern Southbury, Connecticut. That's where you'll find the Southbury Dog Park. This off-leash dog park has separate enclosures for big and small dogs, and there's also a swimming area, although it isn't fenced. Within the park's 14 acres, you'll also find wooded areas for your dog to sniff out and open fields where they can chase a ball. Visitors love how friendly the regulars are at this park, and if you happen to forget your own water, someone is always willing to share theirs!

Foley

24
Dog Parks
1 park

Population Density
1,265 per sq. mi.

Foley

24

Naugatuck is a town just southeast of Middlebury, and the western side of the city is only a 15-minute drive from Middlebury. This is where you'll find the Naugatuck Dog Park, an off-leash dog park known for its lovely setting and welcoming regulars. Within the park's three acres, there are different enclosures for big and little dogs, as well as plenty of seating areas for pet parents. The Naugatuck Dog Park opened in 2017, and it's open daily from sunrise to sunset. The park provides doggy bags, but be sure to bring your own water and bowl to give your dog a drink.

Northwest Wolcott

12
Dog Parks
1 park

Population Density
1,400 per sq. mi.

Northwest Wolcott

12

The northwestern corner of Wolcott, Connecticut is a 20-minute drive from Middlebury, and that's where you'll find Peterson Park. This large green space has playgrounds, sports courts, a skate park, trails, and picnic spots, and it's also home to the town's off-leash park. The Wolcott Dog Park isn't a particularly big dog park, but it includes separate sections for large and small dogs, and there's more than enough room to have some fun! You can also access the Mattatuck Trail from Peterson Park, and this 13-mile trail is a scenic place to take your dog for a walk on a leash.

Mixville/ West Cheshire

0
Dog Parks
1 park

Population Density
785 per sq. mi.

Mixville/ West Cheshire

0

Cheshire is a town west of Middlebury that's home to about 30,000 people. In 15 minutes, you and your dog can drive to northwestern Cheshire, and that's where you'll find the town's off-leash dog park. The Cheshire Dog Park has a section where dogs of all sizes can interact, as well as a separate enclosure just for small dogs. There's also a variety of agility equipment in the park if your dog is looking for extra stimulation. To keep pet parents comfortable, there's a gazebo in the park, as well as other seating areas. Cheshire Dog Park also has a drinking fountain for dogs, and doggy bags are provided, too.