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
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Best dog walkers in Winchester

Book on demand and scheduled walks with local dog walkers

Recommended
Dog Walking

On-demand, scheduled, and recurring walks

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$10

$90

1 mi30 mi
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Best dog walkers in Winchester

Book on demand and scheduled walks with local dog walkers

Recommended

1. Lauren M

Somerville, MA, 02143

from$19

Five stars

5 (14)

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from$19

Somerville, MA, 02143

2. Sana K

Boston, MA, 02118

from$21

Five stars

5 (48)

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from$21

Boston, MA, 02118

3. Christy L

Lexington, MA, 02421

from$16

Five stars

5 (149)

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from$16

Lexington, MA, 02421

4. Sydney S

Boston, MA, 02116

from$18

Five stars

5 (97)

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from$18

Boston, MA, 02116

5. Nicole P

Melrose, MA, 02176

from$19

Five stars

5 (51)

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from$19

Melrose, MA, 02176

6. Annie B

Arlington, MA, 02474

from$16

Five stars

5 (80)

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from$16

Arlington, MA, 02474

7. Casey S

Woburn, MA, 01801

from$16

Five stars

5 (1141)

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from$16

Woburn, MA, 01801

8. Melissa D

Woburn, MA, 01801

from$16

Five stars

5 (18)

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from$16

Woburn, MA, 01801

9. Stephanie L

Arlington, MA, 02476

from$16

Five stars

5 (194)

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from$16

Arlington, MA, 02476

10. Gareth B

Medford, MA, 02155

from$16

Five stars

5 (231)

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from$16

Medford, MA, 02155

11. Stephanie S

Medford, MA, 02155

from$20

Five stars

5 (117)

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from$20

Medford, MA, 02155

12. Sarah P

Medford, MA, 02155

from$16

Five stars

5 (48)

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from$16

Medford, MA, 02155

13. Aileen H

Medford, MA, 02155

from$17

Five stars

5 (48)

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from$17

Medford, MA, 02155

14. Caroline W

Medford, MA, 02155

from$18

Five stars

5 (191)

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from$18

Medford, MA, 02155

15. Sophia L

Cambridge, MA, 02138

from$18

Five stars

5 (92)

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from$18

Cambridge, MA, 02138

16. Bryce C

Somerville, MA, 02144

from$16

Five stars

5 (0)

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from$16

Somerville, MA, 02144

17. Kaeli H

Somerville, MA, 02144

from$16

Five stars

5 (100)

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from$16

Somerville, MA, 02144

18. Meghan K

Wakefield, MA, 01880

from$18

Five stars

5 (189)

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from$18

Wakefield, MA, 01880

19. Kamal H

Somerville, MA, 02144

from$18

Five stars

5 (42)

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from$18

Somerville, MA, 02144

20. Elizabeth K

Medford, MA, 02144

from$16

Five stars

4.9 (9)

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from$16

Medford, MA, 02144

21. Elizabeth P

Woburn, MA, 01801

from$15

Five stars

5 (80)

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from$15

Woburn, MA, 01801

22. Keelin E

Cambridge, MA, 02140

from$18

Five stars

5 (35)

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from$18

Cambridge, MA, 02140

23. Carrigan F

South Portland, ME, 04106

from$17

Five stars

5 (8)

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from$17

South Portland, ME, 04106

24. Edward L

Lexington, MA, 02420

from$17

Five stars

5 (202)

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from$17

Lexington, MA, 02420

25. Allison M

Medford, MA, 02155

from$19

Five stars

5 (191)

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from$19

Medford, MA, 02155

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How to book dog walkers near me
  • Get matched

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  • Follow along

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  • 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.

E L.-avatar

E,

Winchester

Thank you for taking such good care of my mush

Five starsFive starsFive starsFive starsFive stars
Gabrielle V.-avatar

Gabrielle,

Winchester

Thank you! Great route today! Fun to change it up for Juno!

Five starsFive starsFive starsFive starsFive stars
Kate S.-avatar

Kate,

Winchester

Thanks so much for taking him in the rain!!

Five starsFive starsFive starsFive starsFive stars
Karina C.-avatar

Karina,

Winchester

Tysm!! Amazing as always:)

Five starsFive starsFive starsFive starsFive stars
Christina A.-avatar

Christina,

Winchester

Thank you!!

Five starsFive starsFive starsFive starsFive stars
meg D.-avatar

meg,

Winchester

You re amazing thank you thank you thank you

Five starsFive starsFive starsFive starsFive stars
meg D.-avatar

meg,

Winchester

Selena is the best!!! So glad I can trust her to take amazing care of my puppy son!

Five starsFive starsFive starsFive starsFive stars
Holly K.-avatar

Holly,

Winchester

Thank you!!!

Five starsFive starsFive starsFive starsFive stars
marisa C.-avatar

marisa,

Winchester

Thank you so much for being so patient with the pups. We all really appreciate it!

Five starsFive starsFive starsFive starsFive stars
Gabrielle V.-avatar

Gabrielle,

Winchester

Cameron is the best. She always brings juno to the park and I get videos which are so fun. She keeps an extra caring eye on my dog and her report cards are great!

Five starsFive starsFive starsFive starsFive stars
E L.-avatar

E,

Winchester

Thank you for taking such good care of my mush

Five starsFive starsFive starsFive starsFive stars
Gabrielle V.-avatar

Gabrielle,

Winchester

Thank you! Great route today! Fun to change it up for Juno!

Five starsFive starsFive starsFive starsFive stars
Kate S.-avatar

Kate,

Winchester

Thanks so much for taking him in the rain!!

Five starsFive starsFive starsFive starsFive stars
Karina C.-avatar

Karina,

Winchester

Tysm!! Amazing as always:)

Five starsFive starsFive starsFive starsFive stars
Christina A.-avatar

Christina,

Winchester

Thank you!!

Five starsFive starsFive starsFive starsFive stars
meg D.-avatar

meg,

Winchester

You re amazing thank you thank you thank you

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!
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