Dog walking in Winchester

Book on demand and scheduled walks with local dog walkers

How it works

illustration

Flexible scheduling

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

illustration

Customized for your pup

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

illustration

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

Paul VWinchester, MA 01890

4.9

(2692)

Book now

Hi, My name is Paul and I have had rescued three dogs since 1997. I had a large Bull Mastiff / St. Bernard mix named Veego that passed away at around 15 in 2012. I have had a German Shepherd since 2005, Honey is currently 14 years old. I have also had a Staffordshire Bull Terrier named Ben since 2007 that is about to be ten. I have pet sat for lots of friends in the past. Pitbulls, Rotweiller, Labradors, Boxer, Pug, Chihuahuas, French Bulldog, and a few Terriers. Seeing any dog always puts a smile on my face, from abandoned rescues to show dogs. I enjoy learning their unique personalities and quirks. I will treat your dog (and home) like I do my own, with love and care. I've also been vegetarian / vegan for over 25 years and like to stay active. Reliable transportation for North Shore and Boston.

Background Checked

High Demand

Top Pet Caregiver

Ellie GWinchester, MA 01890

4.9

(1657)

Book now

“A walk a day keeps the vet away!”

Hi! I'm Ellie and the most important fact to know about me is; I love animals! I moved to Natick from California where I was a dog walker for five years. I grew up in rural NY, we always had at least two dogs plus a bunch more critters. I recently graduated from Humboldt State University were I studied wildlife biology so I can help save all the animals. I am a natural with dogs of all sizes, some training experience, lots of energy for walks, and I can't wait to meet your best friend!

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

Jill YWinchester, MA 01890

4.9

(1570)

Book now

Hi my name is Jill and I am the proud owner of an English Bulldog, Queen Cookie. I recently moved to Boston and Queen Cookie is living back home in CT with her Grama. I miss walking my furry companion and figured WAG was a great way to fill that void. I am comfortable walying dogs from 10 pounds to 120 pounds and can not wait to meet your fur baby!

Background Checked

High Demand

Gabrielle SWinchester, MA 01890

4.9

(1560)

Book now

Hi there! My name is Gabbi! I'm a Boston native and I've loved animals my whole life. Being able to work with dogs is a dream of mine, so I'll always make sure your best friend is well taken care of!

Background Checked

High Demand

Top Pet Caregiver

Specialties

Fast walker, Dogs who pull, Puppy care

Collin MWinchester, MA 01890

4.9

(1469)

Book now

Hi! I am a very active person who loves the outdoors. I'm an avid runner and also enjoy hiking, backpacking, tennis, cooking, and travel. I look forward to getting to know you and your dog!

Background Checked

High Demand

Top Pet Caregiver

Socially Distanced Pet Care

Specialties

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

Rebekah HWinchester, MA 01890

4.9

(1365)

Book now

Hi, my name is Rebekah. I grew up an animal lover in Maine, I started walking and sitting for my friends’ and neighbors’ pets more than 8 years ago and have loved it ever since! I have experience with dogs of all sizes and ages. As an outdoorsy, active person, I’d love to meet your best friend and take them out for some fun and exciting exercise! I know each pup is as unique as they are loved, and I can’t wait to provide you both with the caring Wag! experience.

Background Checked

High Demand

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, Fast walker, Dogs who pull, Puppy care, Training experience, Obedience training, Behavioral training, Socialization training, Potty training, Therapy training, Service training, Puppy training

Brenda WWinchester, MA 01890

4.9

(1341)

Book now

“Never met a dog I didn't love ❤”

I have been a lover of animals my whole life . Been dog sitting for friends the last 20 years . I consider myself to be a very dependable respon person who will give your dog the love and care it deserves.

Background Checked

High Demand

Top Pet Caregiver

Specialties

Senior dog care, Special needs dog care, Fast walker

Elliott MWinchester, MA 01890

4.9

(1333)

Book now

Hi, I grew in a house with two corgis and a Labrador. I currently do not have a dog but love their company. I have worked as a dog walker before, and i’m excited to meet new dogs in my neighborhood. I’m looking forward to meeting your dog!

Background Checked

High Demand

Top Pet Caregiver

James WWinchester, MA 01890

4.8

(1487)

Book now

I grew up with a Shetland Sheepdog/Collie mix and a Samoyed. In addition I love all animals. When I travel, I make a point to go the the local zoo, if one exists, and pet shops. Also, I lived overseas for twenty years, so I have learned to adapt to all kinds of new circumstances, conditions, surprises etc. Finally, I am conscientious, responsible, honest and reliable.

Background Checked

High Demand

Socially Distanced Pet Care

Miriam LWinchester, MA 01890

4.8

(1317)

Book now

“Ethical, Compassionate & Knowledgeable Walker (:”

Hi, there! I’m a 28 y/o professional full-time pet caregiver! I have 7 years of experience handling pets individually, and through different companies. I take my work very seriously and strive to always provide optimal care, compassion, ethical treatment and safety for each and every dog I meet. I enjoy working with all breeds, ages, disabilities and levels of energy. It is my duty to always treat pets with kindness and patience, as well as abide by owners’ requests! Thank you for choosing me!

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, Fast walker, Dogs who pull, Puppy care, Training experience, Obedience training, Behavioral training, Socialization training, Potty training, Puppy training

Dog Walking in Winchester

The small suburban township of Winchester, located about 10 miles north of Boston, is a neatly organized community set on Wedge Pond and Mill Pond, connected to each other by the Aberjona River. The town’s surroundings offer picturesque views of nature at the nearby parks and reservations, which provide outdoor entertainment for both humans and their furry friends. There aren't so many local businesses and cafes to visit with Fido here, apart from Bruegger's Bagels, but you can always rely on the help of two veterinary clinics in the city center.

Winchester doesn't have many dog-friendly activities of its own, but the surrounding areas have plenty of things for you and Rover to explore! Feel free to enjoy the sandy area of Shannon Beach, which allows leashed dogs to dig in the sand and play in the water. Or, check out Mystic Lakes State Park, boasting a range of walking trails and paths that meander alongside Upper Mystic Lake. Another furrific place for you and your pooch to visit near Winchester is Whipple Hill, a 120-acre conservation area with walking trails, a pond, and diverse animal life.

Winchester is just pawfect for dog owners looking to spend some time away from the hustle and bustle of the big city, while staying close enough to enjoy all its amenities.

Best Dog Neighborhoods in Winchester

Middlesex Fells Reservation

48
Dog Parks
1 park

Population Density
2,410 per sq. mi.

Middlesex Fells Reservation

48

Conveniently set between Stoneham and Medford, Middlesex Fells Reservation is located a short ride east of Winchester, offering a variety of outdoor activities and a great place to find a retreat or spend a day out with your pup. The area offers about 2,500 acres of diverse landscape, panoramic vistas, meadows, and rocky hills suitable for active hiking and exploring! The off-leash area of Sheepfold Dog Park, located in the very heart of the park, is sure to excite every pooch who is tired of walking on their leash. The dog park boasts a huge fenced, open space for furry friends to chase and play with each other to their hearts' content.

Wyoming

36
Dog Parks
1 park

Population Density
10,678 per sq. mi.

Wyoming

36

Wyoming is a central neighborhood in Melrose with a well-developed infrastructure and a dog-friendly attitude. You will find the crystal clear Ell Pond to the north, with Ell Pond Park situated on its banks. Apart from Ell Pond Lake Trail, this park also features a dog park! Melrose Dog Park is a furrific spot with two separate sections for small and large breeds, a fence, lots of comfortable benches for owners and drinking water stations for thirsty pups! Going out on empty stomach is a bad idea, so take a look at the menu in D’Amici’s Bakery, where you can share a sweet treat at the outdoor tables before heading to the park.

Southeast Medford

24
Dog Parks
1 park

Population Density
5,624 per sq. mi.

Southeast Medford

24

If you follow the lead of the Mystic River from the city center of Medford to the east, you'll find a pleasant surprise waiting for you and your puppy halfway! Medford Dog Park, conveniently situated on the banks of the river, is a cool place to have a great day out with Fido! This neatly organized and well-maintained dog park has a fence, a paved walking trail, benches, and plenty of canine companions to play with, who usually visit in the evening. You will have to bring your own drinking water, or stop by Smashburger or Panera Bread, located a few miles away from the park near the shopping area. Share a quick bite at the outdoor tables with your leashed pup.

City Center Arlington

12
Population Density
13,973 per sq. mi.

City Center Arlington

12

If you travel south of Winchester, you will eventually reach Arlington. Its busy Massachusetts Avenue is home to plenty of small local businesses in the city center. Apart from that, a small oasis of peace and quiet is waiting for you and your pooch in Whittemore-Robbins House Park. This public park has walking trails which offer stunning views of the Boston skyline. Dogs are allowed to explore the park off-leash during designated hours, from 6 am to 9 am daily. The Minuteman Bikeway, stretching for about 9 miles from West Cambridge to Bedford, is another pawfect place for walkies! Bring water and waste bags with you.

Horn Pond Recreation Area

0
Population Density
2,863 per sq. mi.

Horn Pond Recreation Area

0

If you explore the surrounding areas north of Winchester, you will find Horn Pond Recreation Area nestled on -- you guessed it -- Horn Pond. This beautiful place in Woburn, with picturesque views and a wealth of outdoor activities for humans and pooches alike, is a wonderful retreat for a day or a weekend. There is plenty of excitement for dogs just off the main lake, on the winding walking trails. If you decide to have a walk in the evening, stay for a while to see the sunset. Remember to keep your pup on the leash and clean up after them to keep the area beautiful!