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Best dog walkers in Winchester

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Dog Walking

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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

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Jessica M avatar

1. Jessica M

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Chelsea, MA, 02150

from$18

Five stars

5 (6)

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from$18

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Chelsea, MA, 02150

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CHRISTIAN P avatar

2. CHRISTIAN P

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Boston, MA, 02128

from$19

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4.8 (376)

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from$19

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Boston, MA, 02128

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Steven D avatar

3. Steven D

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Somerville, MA, 02144

from$19

Five stars

4.9 (120)

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from$19

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Somerville, MA, 02144

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Maria F avatar

4. Maria F

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Boston, MA, 02115

from$19

Five stars

5 (37)

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from$19

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Boston, MA, 02115

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Ethan M avatar

5. Ethan M

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Boston, MA, 02210

from$17

Five stars

4.9 (77)

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from$17

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Boston, MA, 02210

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Emma E avatar

6. Emma E

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Winchester, MA, 01890

from$16

Five stars

5 (43)

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from$16

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Winchester, MA, 01890

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Casey S avatar

7. Casey S

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Woburn, MA, 01801

from$16

Five stars

4.9 (1022)

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from$16

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Woburn, MA, 01801

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Sean G avatar

8. Sean G

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Somerville, MA, 02144

from$16

Five stars

4.9 (89)

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from$16

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Somerville, MA, 02144

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Nikita V avatar

9. Nikita V

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Stoneham, MA, 02180

from$16

Five stars

5 (0)

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from$16

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Stoneham, MA, 02180

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Kimm S avatar

10. Kimm S

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Woburn, MA, 01801

from$17

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4.9 (655)

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from$17

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Woburn, MA, 01801

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Eden V avatar

11. Eden V

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Lexington, MA, 02420

from$16

Five stars

5 (55)

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from$16

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Lexington, MA, 02420

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Julia G avatar

12. Julia G

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Arlington, MA, 02474

from$18

Five stars

5 (27)

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from$18

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Arlington, MA, 02474

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Zach A avatar

13. Zach A

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Arlington, MA, 02474

from$16

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4.9 (287)

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from$16

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Arlington, MA, 02474

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Kelly H avatar

14. Kelly H

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Medford, MA, 02155

from$19

Five stars

4.9 (35)

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from$19

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Medford, MA, 02155

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Gareth B avatar

15. Gareth B

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Medford, MA, 02155

from$16

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4.9 (193)

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from$16

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Medford, MA, 02155

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Harrison B avatar

16. Harrison B

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Medford, MA, 02155

from$16

Five stars

5 (4)

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from$16

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Medford, MA, 02155

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Lindsay L avatar

17. Lindsay L

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Arlington, MA, 02474

from$15

Five stars

4.9 (806)

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from$15

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Arlington, MA, 02474

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Reagan R avatar

18. Reagan R

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Medford, MA, 02155

from$15

Five stars

5 (11)

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from$15

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Medford, MA, 02155

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Chris O avatar

19. Chris O

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Medford, MA, 02155

from$16

Five stars

4.9 (146)

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from$16

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Medford, MA, 02155

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Maria A avatar

20. Maria A

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Melrose, MA, 02176

from$16

Five stars

5 (10)

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from$16

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Melrose, MA, 02176

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John K avatar

21. John K

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Medford, MA, 02155

from$15

Five stars

4.8 (79)

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from$15

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Medford, MA, 02155

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Kai P avatar

22. Kai P

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Medford, MA, 02155

from$17

Five stars

4.9 (177)

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from$17

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Medford, MA, 02155

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Kaeli H avatar

23. Kaeli H

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Medford, MA, 02144

from$16

Five stars

5 (67)

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from$16

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Medford, MA, 02144

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Jacquelyn B avatar

24. Jacquelyn B

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Lexington, MA, 02421

from$15

Five stars

5 (9)

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from$15

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Lexington, MA, 02421

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Mikayla C avatar

25. Mikayla C

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Burlington, MA, 01803

from$18

Five stars

4.4 (15)

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from$18

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Burlington, MA, 01803

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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

Read reviews of Winchester, MA dog walkers

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2048 reviews

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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

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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.

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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鈥橝mici鈥檚 Bakery, where you can share a sweet treat at the outdoor tables before heading to the park.

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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.

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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.

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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

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