Dog Walkers in Winchester, MA

Find trusted dog walkers near you.

How Wag! Works

Book a Dog Walk with One of our Trusted Wag! Walkers
Track your Dog's Walk with our Live GPS Tracker
Receive Custom Reports Detailing your Dog's Activity

Vetted Walker Trust & Safety

Thoroughly Vetted
Insured & Bonded
Wag! Guaranteed

Featured Walkers Near You

Dog Areas in Winchester, MA

1 Shop
1 Eatery
3 Groomers

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, MA

  1. Dog Parks 1
    Population Density 2,410/sq mi

    #1 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.

    Dog neighborhood?
  2. Dog Parks 1
    Population Density 10,678/sq mi

    #2 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.

    Dog neighborhood?
  3. Dog Parks 1
    Population Density 5,624/sq mi

    #3 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.

    Dog neighborhood?
  4. Dog Parks 0
    Population Density 13,973/sq mi

    #4 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.

    Dog neighborhood?
  5. Dog Parks None
    Population Density 2,863/sq mi

    #5 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!

    Dog neighborhood?
Book me a walkiee?
Pweeeze!
Sketch of smiling australian shepherd