Dog walking in Winchester

Book on demand and scheduled walks with local dog walkers

Book now
Dog walking

How to book dog walkers near me

  • Get matched

    Get matched

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

  • Follow along

    Follow along

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

  • Get a report card

    Get a report card

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

    • Get matched

      Get matched

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

    • Follow along

      Follow along

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

    • Get a report card

      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.

    Browse top-rated dog walkers in Winchester, MA 01890

    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

    Background Checked

    High Demand

    High Demand

    Top Pet Caregiver

    Top Pet Caregiver


    CherryAnn G.
    2019-11-18T09:46:56-08:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    I grew up with a Shetland Sheepdog/Border 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

    Background Checked

    High Demand

    High Demand

    Socially Distanced Pet Care

    Socially Distanced Pet Care

    Specialties

    Oral medicine administration, Senior dog care, Special needs dog care, High energy dogs, Dogs who pull, Puppy care, Therapy training, Puppy training


    Toni A.
    2022-08-06T03:48:07-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    “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

    Background Checked

    High Demand

    High Demand

    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


    Jaleesa G.
    2017-06-20T06:47:20-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    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

    Background Checked

    High Demand

    High Demand

    Socially Distanced Pet Care

    Socially Distanced Pet Care

    Specialties

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


    Jaime D.
    2022-06-26T13:01:32-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    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

    Background Checked

    High Demand

    High Demand


    Toni A.
    2022-07-23T09:07:05-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    Hi there! My name is Gabbi! I'm a South Shore 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

    Background Checked

    High Demand

    High Demand

    Specialties

    Fast walker, Dogs who pull, Puppy care


    lauren C.
    2022-02-08T19:16:41-08:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    I am taking classes online right now and my time is flexible. I have an English Bulldog named Henry who only ever wants to go for car rides. I am always trying to find ways to exercise and keep moving so I would truly love to play or walk with your dog.

    Background Checked

    Background Checked

    High Demand

    High Demand

    Top Pet Caregiver

    Top Pet Caregiver

    Specialties

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


    Niccolo O.
    2021-08-24T08:54:37-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    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

    Background Checked

    High Demand

    High Demand


    Craig D.
    2021-07-28T10:35:20-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    “Experienced & Knowledgeable Walker”

    Hi, there! I’m Miriam, I’m 29 and I have 8 years of dog walking and pet sitting experience. I firmly believe that all dogs are good dogs and work with dogs all breeds, ages, personalities and levels of energy.

    Background Checked

    Background Checked

    High Demand

    High Demand

    Socially Distanced Pet Care

    Socially Distanced Pet Care

    Specialties

    Dog first aid and/or CPR, 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, Behavioral training, Socialization training


    Morgan L.
    2022-07-06T09:49:19-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    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

    Background Checked

    High Demand

    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


    Rebecca Felhazy Zuman Z.
    2020-03-02T09:18:21-08:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    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

    Background Checked

    High Demand

    High Demand

    Top Pet Caregiver

    Top Pet Caregiver


    CherryAnn G.
    2019-11-18T09:46:56-08:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    I grew up with a Shetland Sheepdog/Border 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

    Background Checked

    High Demand

    High Demand

    Socially Distanced Pet Care

    Socially Distanced Pet Care

    Specialties

    Oral medicine administration, Senior dog care, Special needs dog care, High energy dogs, Dogs who pull, Puppy care, Therapy training, Puppy training


    Toni A.
    2022-08-06T03:48:07-07:00
    Five starsFive starsFive starsFive starsFive stars
    Verified 20m Walk

    More about dog walking in Winchester, MA 01890

    Hours

     - 

    Star

    Average rating

    star rating

    4.95


    Price range

    $23.50 - $32.88

    Dog walking FAQs

    How much does a dog walk cost in Winchester, MA 01890?

    plus-wag-green-icon

    How do I find and choose a dog walker in Winchester, MA 01890?

    plus-wag-green-icon

    How long does a dog walk last in Winchester, MA 01890?

    plus-wag-green-icon

    How to book a dog walk in Winchester, MA 01890?

    plus-wag-green-icon

    Didn't find the answer? Visit our FAQ page

    Read reviews of Winchester, MA 01890 dog walkers

  • avatar

    CherryAnn G.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Chelsea is overrun with bad dog owners!

    avatar

    Paul V

    Book now
  • avatar

    Toni A.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Thank you!

    avatar

    James W

    Book now
  • avatar

    Jaleesa G.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Ellie! You are awesome. That video made my day. Jermaine's anthem, for sure!

    avatar

    Ellie G

    Book now
  • avatar

    Jaime D.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Thank you so much!

    avatar

    Collin M

    Book now
  • avatar

    Toni A.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    You re the best - as always! Chevy and I thank you.

    avatar

    Jill Y

    Book now
  • avatar

    lauren C.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Aww thank you so much! I will request you next time

    avatar

    Gabrielle S

    Book now
  • avatar

    Niccolo O.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Great picture. Thanks Richie.

    avatar

    Richie C

    Book now
  • avatar

    Craig D.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Had a different routine a little more complicated than usual because of houseguests. He was able to make it happen seamlessly. Nice job, Bailey loves this guy as a walker.

    avatar

    Elliott M

    Book now
  • avatar

    Morgan L.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    Thank you so much Miriam! :) really appreciate you making sure she didn t overheat

    avatar

    Miriam L

    Book now
  • avatar

    Rebecca Felhazy Zuman Z.

    Five starsFive starsFive starsFive starsFive stars

    Verified 20m Walk

    LOVED report card. Thx!

    avatar

    Rebekah H

    Book now
    • avatar

      CherryAnn G.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Chelsea is overrun with bad dog owners!

      avatar

      Paul V

      Book now
    • avatar

      Toni A.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Thank you!

      avatar

      James W

      Book now
    • avatar

      Jaleesa G.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Ellie! You are awesome. That video made my day. Jermaine's anthem, for sure!

      avatar

      Ellie G

      Book now
    • avatar

      Jaime D.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Thank you so much!

      avatar

      Collin M

      Book now
    • avatar

      Toni A.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      You re the best - as always! Chevy and I thank you.

      avatar

      Jill Y

      Book now
    • avatar

      lauren C.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Aww thank you so much! I will request you next time

      avatar

      Gabrielle S

      Book now
    • avatar

      Niccolo O.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Great picture. Thanks Richie.

      avatar

      Richie C

      Book now
    • avatar

      Craig D.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Had a different routine a little more complicated than usual because of houseguests. He was able to make it happen seamlessly. Nice job, Bailey loves this guy as a walker.

      avatar

      Elliott M

      Book now
    • avatar

      Morgan L.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      Thank you so much Miriam! :) really appreciate you making sure she didn t overheat

      avatar

      Miriam L

      Book now
    • avatar

      Rebecca Felhazy Zuman Z.

      Five starsFive starsFive starsFive starsFive stars

      Verified 20m Walk

      LOVED report card. Thx!

      avatar

      Rebekah H

      Book now

    Best Dog Friendly Neighborhoods in Winchester

    Middlesex Fells Reservation

    4848
    Dog ParksDog Parks
    1 park

    Population DensityPopulation Density
    2,410 per sq. mi.

    Middlesex Fells Reservation

    4848

    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

    3636
    Dog ParksDog Parks
    1 park

    Population DensityPopulation Density
    10,678 per sq. mi.

    Wyoming

    3636

    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

    2424
    Dog ParksDog Parks
    1 park

    Population DensityPopulation Density
    5,624 per sq. mi.

    Southeast Medford

    2424

    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

    1212
    Population DensityPopulation Density
    13,973 per sq. mi.

    City Center Arlington

    1212

    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

    00
    Population DensityPopulation Density
    2,863 per sq. mi.

    Horn Pond Recreation Area

    00

    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!

    Middlesex Fells Reservation

    4848
    Dog ParksDog Parks
    1 park

    Population DensityPopulation Density
    2,410 per sq. mi.

    Middlesex Fells Reservation

    4848

    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

    3636
    Dog ParksDog Parks
    1 park

    Population DensityPopulation Density
    10,678 per sq. mi.

    Wyoming

    3636

    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

    2424
    Dog ParksDog Parks
    1 park

    Population DensityPopulation Density
    5,624 per sq. mi.

    Southeast Medford

    2424

    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

    1212
    Population DensityPopulation Density
    13,973 per sq. mi.

    City Center Arlington

    1212

    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

    00
    Population DensityPopulation Density
    2,863 per sq. mi.

    Horn Pond Recreation Area

    00

    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!

    Learn more in the Wag! app

    Five starsFive starsFive starsFive starsFive stars

    43k+ reviews

    Install


    © 2022 Wag Labs, Inc. All rights reserved.