Dog walking in Winchester

Book on-demand and scheduled walks with local dog walkers - choose between a 20-minute, 30-minute, or 60-minute walk for your pup
Need a walk ASAP? Let Wag! match you with a top-rated dog walker near you.
Best dog walkers in Winchester

Book on demand and scheduled walks with local dog walkers

Recommended
Dog Walking

On-demand, scheduled, and recurring walks

Type to search cities...

$10

$90

1 mi30 mi
Pet Experience
Training Experience
Health Wellness
Best dog walkers in Winchester

Book on demand and scheduled walks with local dog walkers

Recommended

1. Elizabeth T

South Boston, MA, 02127

from$16

Five stars

5 (28)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

South Boston, MA, 02127

2. Sydney S

Boston, MA, 02116

from$18

Five stars

5 (90)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Boston, MA, 02116

3. Allison M

Medford, MA, 02155

from$19

Five stars

5 (179)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$19

Medford, MA, 02155

4. Skylar W

East Boston, MA, 02128

from$18

Five stars

5 (511)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

East Boston, MA, 02128

5. Susan B

Everett, MA, 02149

from$19

Five stars

5 (147)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$19

Everett, MA, 02149

6. Abigail S

Medford, MA, 02155

from$18

Five stars

5 (110)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Medford, MA, 02155

7. Katherine P

Winchester, MA, 01890

from$16

Five stars

5 (77)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Winchester, MA, 01890

8. Aubrey H

Arlington, MA, 02474

from$18

Five stars

5 (80)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Arlington, MA, 02474

9. Casey M

Medford, MA, 02155

from$18

Five stars

5 (370)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Medford, MA, 02155

10. Casey S

Woburn, MA, 01801

from$16

Five stars

5 (1140)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Woburn, MA, 01801

11. Carrie V

Arlington, MA, 02476

from$18

Five stars

5 (111)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Arlington, MA, 02476

12. Gareth B

Medford, MA, 02155

from$16

Five stars

5 (227)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Medford, MA, 02155

13. Cayla B

Medford, MA, 02155

from$16

Five stars

5 (149)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Medford, MA, 02155

14. Narali T

Medford, MA, 02155

from$18

Five stars

5 (17)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Medford, MA, 02155

15. Hannah L

Stoneham, MA, 02180

from$18

Five stars

5 (171)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Stoneham, MA, 02180

16. Caroline W

Medford, MA, 02155

from$18

Five stars

5 (166)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Medford, MA, 02155

17. Mia S

Medford, MA, 02155

from$16

Five stars

5 (47)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Medford, MA, 02155

18. Victoria T

Woburn, MA, 01801

from$16

Five stars

5 (86)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Woburn, MA, 01801

19. Kamal H

Somerville, MA, 02144

from$18

Five stars

5 (39)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Somerville, MA, 02144

20. Seneca D

arlington, MA, 02452

from$18

Five stars

5 (7)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

arlington, MA, 02452

21. Katie M

Brookline, MA, 02445

from$16

Five stars

5 (171)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$16

Brookline, MA, 02445

22. Elizabeth P

Woburn, MA, 01801

from$15

Five stars

5 (78)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Woburn, MA, 01801

23. Matthew M

Stoneham, MA, 02180

from$15

Five stars

4.9 (65)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$15

Stoneham, MA, 02180

24. Clare E

Cambridge, MA, 02140

from$18

Five stars

5 (61)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$18

Cambridge, MA, 02140

25. Edward L

Lexington, MA, 02420

from$17

Five stars

5 (198)

Walk ·

Drop-In ·

Sitting ·

Boarding

from$17

Lexington, MA, 02420

1

2

3

4

5

How to book dog walkers near me
  • Get matched

    A top-rated local Caregiver will match with you; or you can choose to browse Caregivers near you.

  • Follow along

    Receive live updates and photos. Track your pup's walk via GPS.

  • Get a report card

    Once your pet is home, view details on how the walk went, complete with a photo!

Why find pet care through Wag!?

Wag! is the nation's fastest-growing network of vetted and background checked pet sitters, overnight boarding, dog walkers, dog trainers, and even virtual vet chat. Schedule ahead for pet care while you are away, or book on-demand pet care during the workday. In 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.

Customer Reviews

Unable to take your dog on a walk today? Dog Walkers through Wag! are available to care for your pup whenever you’re not. Every dog walker has passed an enhanced background check. Get photos and updates on where your dog poops and pees while you follow along via GPS in the app.

Bryan W.-avatar

Bryan,

Winchester

Thank you! And so sorry we forgot to put the outside light on!

Five starsFive starsFive starsFive starsFive stars
Kylynn S.-avatar

Kylynn,

Winchester

Thanks for caring for Lay today!! I really appreciate it!

Five starsFive starsFive starsFive starsFive stars
Gabrielle V.-avatar

Gabrielle,

Winchester

Awesome report card, great route (Juno s fave) and thanks for the video updates. Cameron is the best!

Five starsFive starsFive starsFive starsFive stars
Holly K.-avatar

Holly,

Winchester

Martina is the best, my dogs love her!

Five starsFive starsFive starsFive starsFive stars
Olivia M.-avatar

Olivia,

Winchester

Thank you so much for walking my pup and giving him exactly what he needed!

Five starsFive starsFive starsFive starsFive stars
Gabrielle V.-avatar

Gabrielle,

Winchester

Cameron is the best. Thanks for taking good care of Juno as she s recovering from a tummy bug, and watching her on the walk and avoiding bunny poops (her favorite). Juno is always well cared for and has an adventurous fun walk with Cameron.!

Five starsFive starsFive starsFive starsFive stars
Hafiza Y.-avatar

Hafiza,

Winchester

Thanks Christian!

Five starsFive starsFive starsFive starsFive stars
Melissa R.-avatar

Melissa,

Winchester

My dog loves her walks with Abigail!

Five starsFive starsFive starsFive starsFive stars
Dirk E.-avatar

Dirk,

Winchester

Thank you!

Five starsFive starsFive starsFive starsFive stars
Nicole and Ali E.-avatar

Nicole,

Winchester

Thank you!!

Five starsFive starsFive starsFive starsFive stars
Bryan W.-avatar

Bryan,

Winchester

Thank you! And so sorry we forgot to put the outside light on!

Five starsFive starsFive starsFive starsFive stars
Kylynn S.-avatar

Kylynn,

Winchester

Thanks for caring for Lay today!! I really appreciate it!

Five starsFive starsFive starsFive starsFive stars
Gabrielle V.-avatar

Gabrielle,

Winchester

Awesome report card, great route (Juno s fave) and thanks for the video updates. Cameron is the best!

Five starsFive starsFive starsFive starsFive stars
Holly K.-avatar

Holly,

Winchester

Martina is the best, my dogs love her!

Five starsFive starsFive starsFive starsFive stars
Olivia M.-avatar

Olivia,

Winchester

Thank you so much for walking my pup and giving him exactly what he needed!

Five starsFive starsFive starsFive starsFive stars
Gabrielle V.-avatar

Gabrielle,

Winchester

Cameron is the best. Thanks for taking good care of Juno as she s recovering from a tummy bug, and watching her on the walk and avoiding bunny poops (her favorite). Juno is always well cared for and has an adventurous fun walk with Cameron.!

Five starsFive starsFive starsFive starsFive stars
Why book a dog walker in Winchester?

Is your pup ready for a stroll around the neighborhood? Find local dog walkers in Winchester, MA who are background checked and vetted by Wag!. Easily schedule recurring walks ahead of time for days when you're in the office, or book on demand when you're out on the town and can't get home in time to walk your dog. Wag! is here to help you ensure your pup can enjoy the sniffs and sights around your Winchester, MA neighborhood, even sending you pictures during the walk and notifications when your furry family member does their business.

The best dog friendly neighborhoods in Winchester
48

Middlesex Fells Reservation

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.
36

Wyoming

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.
24

Southeast Medford

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.
12

City Center Arlington

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.
0

Horn Pond Recreation Area

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!
Frequently asked questions
How much does a dog walk cost in Winchester, MA?
How do I find and choose a dog walker in Winchester, MA?
How long does a dog walk last in Winchester, MA?
How to book a dog walk in Winchester, MA?

Learn more in the Wag! app

Five starsFive starsFive starsFive starsFive stars

43k+ reviews

Install


© 2025 Wag Labs, Inc. All rights reserved.


© 2025 Wag Labs, Inc. All rights reserved.