Dog walking in Winchester

Book on demand and scheduled walks with local dog walkers

How it works

Flexible scheduling

Select the date and time that best suit your needs. Want a walk ASAP? We’ve got you covered.

Customized for your pup

Choose between a 20-minute, 30-minute, or 60-minute stroll for your dog.

Follow along

Track your walk with our live GPS tracker, then view your detailed report card after the walk.

What is Wag!?

Wag! is the nation's fastest-growing network of pre-screened and insured pet sitters and dog walkers. In less than 15 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.

Book walkers near you

Sarah KWinchester, MA 01890

5.0

(1047)

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I love dogs! I have experience with all sizes from XS Pomeranians to XL St. Bernard’s and Newfies, and everything in between. I'm a very active surfer, yogi, and hiker all over New England and love being out in the elements, including rain and snow. I spend a lot of time at the beach in any weather! I also work at South Boston Animal Hospital-you may have seen me behind the front desk. I would love to take your pup with me on a safe and fun adventure around the neighborhood!

Background Checked

High Demand

Top Pet Caregiver

Specialties

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

Gabrielle SWinchester, MA 01890

4.9

(1514)

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Hi there! My name is Gabbi! I'm a Boston 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!

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High Demand

Top Pet Caregiver

Specialties

Dogs who pull, Puppy care, Fast walker

Rebekah HWinchester, MA 01890

4.9

(1364)

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Hi, my name is Rebekah. I grew up an animal lover in Maine, where I enjoyed living with a Blue Heeler/Sheppard mix named Sitka. I started walking and sitting for my friends’ and neighbors’ pets more than 5 years ago and have loved it ever since! Recently I’ve moved to Boston and am excited to be back in the area. 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.

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High Demand

Brenda WWinchester, MA 01890

4.9

(1340)

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“Never met a dog I didn't love ❤”

I have been a lover of animals my whole life . Been dog sitting for friends the last 20 years . I consider myself to be a very dependable respon person who will give your dog the love and care it deserves.

Background Checked

High Demand

Top Pet Caregiver

Specialties

Senior dog care, Special needs dog care, Fast walker

Aidan FWinchester, MA 01890

4.9

(1209)

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“my strengths are distance care and being thorough!”

Hi, my name is Aidan. When I was little I had a black lab named Satch that I loved very much, and that has shown me the joy of caring for animals.I have experience in college caring for dogs in multiple situations and am confident in my abiility to adapt to the needs of individual dogs. I am also a very active person and am excited to take your dogs on very thorough walks! Also, I am a photography graduate from MCAD have experience taking pictures of dogs. Can't wait to meet you and your dogs!

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Top Pet Caregiver

Juliana RWinchester, MA 01890

4.9

(447)

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Hi! My name is Juliana! I'm at FT student at ODU. I grew up with a Poodle, and have lived with and cared for other breeds of different sizes and ages. I am a fur mommy to 2 Pits. I very much enjoy exercising and being outside. Since I'm a very active person, I would love have the opportunity to take your dog on many fun filled walks! As well as a relaxed walk through the neighborhood. I will treat your baby as if they were my own! I look forward to meeting you & your dog! (:

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High Demand

Top Pet Caregiver

Socially Distanced Pet Care

Specialties

Can run with dogs, Oral medicine administration, Senior dog care, Special needs dog care, Dogs who pull, Puppy care, Fast walker

Collin MWinchester, MA 01890

4.9

(1151)

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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

High Demand

Top Pet Caregiver

Socially Distanced Pet Care

Specialties

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

Rafael HWinchester, MA 01890

4.9

(1060)

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Hey there! I'm Rafael. I have owned and taken care of both small and large dogs my entire life, from Jack Russel Terriers to American Pit Bulls, I have experience with them all!! I am good at reading dog behavior and what they want and how they are feeling. Caring for dogs is my great passion in life and I can not wait to meet yours!!!

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Kia MWinchester, MA 01890

4.9

(1012)

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Hi! My name is Kia and I'm originally from Long Island where I have a high- energy wheaten terrier named Roxy. I loved walking with her and with many other neighborhood dogs that I took care of throughout the years. I'm very excited to meet you and your dog!

Background Checked

High Demand

Specialties

Senior dog care, Special needs dog care, High energy dogs, Dogs who pull, Puppy care, Fast walker

Miriam LWinchester, MA 01890

4.8

(1289)

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“Compassionate, caring, experienced caregiver”

**I have been tested negative for Covid-19** Hello! My name is Miriam, I am 27, an enthusiastic dog lover, as well as self-employed dog sitter, boarder, walker and trainer! I have had a loyal client base in the greater Boston area for the past several years that has only been growing, which I am so grateful for. I strive to provide optimal care and safety for each and every dog!

Background Checked

High Demand

Socially Distanced Pet Care

Specialties

Dog first aid and/or CPR, Can run with dogs, Oral medicine administration, Injected medicine administration, Senior dog care, High energy dogs, Training experience, Dogs who pull, Puppy care

Dog Walking in Winchester

The small suburban township of Winchester, located about 10 miles north of Boston, is a neatly organized community set on Wedge Pond and Mill Pond, connected to each other by the Aberjona River. The town’s surroundings offer picturesque views of nature at the nearby parks and reservations, which provide outdoor entertainment for both humans and their furry friends. There aren't so many local businesses and cafes to visit with Fido here, apart from Bruegger's Bagels, but you can always rely on the help of two veterinary clinics in the city center.

Winchester doesn't have many dog-friendly activities of its own, but the surrounding areas have plenty of things for you and Rover to explore! Feel free to enjoy the sandy area of Shannon Beach, which allows leashed dogs to dig in the sand and play in the water. Or, check out Mystic Lakes State Park, boasting a range of walking trails and paths that meander alongside Upper Mystic Lake. Another furrific place for you and your pooch to visit near Winchester is Whipple Hill, a 120-acre conservation area with walking trails, a pond, and diverse animal life.

Winchester is just pawfect for dog owners looking to spend some time away from the hustle and bustle of the big city, while staying close enough to enjoy all its amenities.

Best Dog Neighborhoods in Winchester

Middlesex Fells Reservation

48
Dog Parks
1 park

Population Density
2,410 per sq. mi.

Middlesex Fells Reservation

48

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

36
Dog Parks
1 park

Population Density
10,678 per sq. mi.

Wyoming

36

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

24
Dog Parks
1 park

Population Density
5,624 per sq. mi.

Southeast Medford

24

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

12
Population Density
13,973 per sq. mi.

City Center Arlington

12

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

0
Population Density
2,863 per sq. mi.

Horn Pond Recreation Area

0

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!