Dog walking in Winchester

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Best dog walkers in Winchester

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$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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Luis  D avatar

1. Luis D

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Brighton, MA, 02135

from$16

Five stars

5 (151)

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from$16

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Brighton, MA, 02135

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Casey M avatar

2. Casey M

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Medford, MA, 02155

from$18

Five stars

5 (68)

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from$18

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Medford, MA, 02155

Promoted Caregiver
Karolina D avatar

3. Karolina D

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Saugus, MA, 01906

from$19

Five stars

5 (174)

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from$19

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Saugus, MA, 01906

Promoted Caregiver
Adrienne M avatar

4. Adrienne M

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Location icon

Newton, MA, 02458

from$18

Five stars

5 (52)

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from$18

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Newton, MA, 02458

Promoted Caregiver
Michaela M avatar

5. Michaela M

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Boston, MA, 02127

from$16

Five stars

5 (168)

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from$16

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Boston, MA, 02127

Aubrey H avatar

6. Aubrey H

Wag! Expert icon
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Arlington, MA, 02474

from$18

Five stars

5 (32)

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from$18

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Arlington, MA, 02474

Casey S avatar

7. Casey S

Wag! Expert icon
Location icon

Woburn, MA, 01801

from$16

Five stars

5 (1102)

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from$16

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Woburn, MA, 01801

David R avatar

8. David R

Wag! Expert icon
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Cambridge, MA, 02140

from$17

Five stars

5 (218)

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from$17

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Cambridge, MA, 02140

Kimm S avatar

9. Kimm S

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Location icon

Woburn, MA, 01801

from$17

Five stars

5 (660)

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from$17

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Woburn, MA, 01801

Julia G avatar

10. Julia G

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Arlington, MA, 02474

from$18

Five stars

5 (64)

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from$18

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Arlington, MA, 02474

Gareth B avatar

11. Gareth B

Wag! Expert icon
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Medford, MA, 02155

from$16

Five stars

5 (217)

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from$16

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Medford, MA, 02155

Sarah P avatar

12. Sarah P

Wag! Expert icon
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Medford, MA, 02155

from$16

Five stars

5 (36)

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from$16

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Medford, MA, 02155

Cayla B avatar

13. Cayla B

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Medford, MA, 02155

from$16

Five stars

5 (140)

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from$16

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Medford, MA, 02155

Mee Thlen M avatar

14. Mee Thlen M

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Medford, MA, 02155

from$16

Five stars

5 (0)

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from$16

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Medford, MA, 02155

Hannah L avatar

15. Hannah L

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Stoneham, MA, 02180

from$18

Five stars

5 (151)

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from$18

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Stoneham, MA, 02180

Mia S avatar

16. Mia S

Wag! Expert icon
Location icon

Medford, MA, 02155

from$16

Five stars

5 (27)

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from$16

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Medford, MA, 02155

Aaron C avatar

17. Aaron C

Wag! Expert icon
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Medford, MA, 02155

from$16

Five stars

5 (76)

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from$16

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Medford, MA, 02155

Mikayla C avatar

18. Mikayla C

Wag! Expert icon
Location icon

Burlington, MA, 01803

from$19

Five stars

5 (62)

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from$19

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Burlington, MA, 01803

Sarah H avatar

19. Sarah H

Wag! Expert icon
Location icon

Boston, MA, 02116

from$16

Five stars

5 (5)

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from$16

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Boston, MA, 02116

Kaeli H avatar

20. Kaeli H

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Location icon

Somerville, MA, 02144

from$16

Five stars

5 (95)

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from$16

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Somerville, MA, 02144

Nicole S avatar

21. Nicole S

Wag! Expert icon
Location icon

Somerville, MA, 02144

from$16

Five stars

5 (9)

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Boarding

from$16

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Somerville, MA, 02144

Elizabeth P avatar

22. Elizabeth P

Wag! Expert icon
Location icon

Woburn, MA, 01801

from$15

Five stars

5 (73)

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Sitting ·

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from$15

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Woburn, MA, 01801

Olivia S avatar

23. Olivia S

Wag! Expert icon
Location icon

Medford, MA, 02155

from$16

Five stars

5 (67)

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Sitting ·

Boarding

from$16

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Medford, MA, 02155

Edward L avatar

24. Edward L

Wag! Expert icon
Location icon

Lexington, MA, 02420

from$17

Five stars

5 (182)

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Boarding

from$17

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Lexington, MA, 02420

Aya C avatar

25. Aya C

Wag! Expert icon
Location icon

Malden, MA, 02148

from$16

Five stars

5 (6)

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from$16

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Malden, MA, 02148

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Why find pet care through Wag!?

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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.

Viren P.-avatar

Viren,

Winchester

Thank you

Five starsFive starsFive starsFive starsFive stars
Ryan S.-avatar

Ryan,

Winchester

Clarissa was literally amazing with Rosie. She was recently discharged from the hospital and Clarissa took the time to be thorough with her updates and even give rosie extra love and rub her tummy and sit with her a litttle longer after their walk, Rosie was in great hands while I was at work

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Patrick D.-avatar

Patrick,

Winchester

The best! Judy has gotten to know my dog really well couldn t recommend her enough!

Five starsFive starsFive starsFive starsFive stars
Mary L.-avatar

Mary,

Winchester

Clara is amazing! My super picky dog loves her!

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Emily G.-avatar

Emily,

Winchester

Joseph is always on time and great with my dog!

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Hafiza Y.-avatar

Hafiza,

Winchester

Thank you!!

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Danielle M.-avatar

Danielle,

Winchester

Thank you so much! Penny had a wonderful time and is nice and tired out.

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Heidi G.-avatar

Heidi,

Winchester

Nice to know Victoria is in the neighborhood!

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khadijah W.-avatar

khadijah,

Winchester

Thank you so much!

Five starsFive starsFive starsFive starsFive stars
Holly S.-avatar

Holly,

Winchester

One of the best, most caring dog walkers we ve had!

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

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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’Amici’s 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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