Dog Walkers in Chesterfield, 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
Wag! Guaranteed

Dog Areas in Chesterfield, MA

1 Park
1 Trail
1 Shop
3 Eateries

The Town of Chesterfield, between Northampton and Pittsfield, was created in 1739 and given to King Philip's and King William's war veterans. The town center was established after the Revolution. In the early days, the community was largely Merino sheep farms and later became industrialized with sawmills, tanneries, and cloth mills. Today, this rural recreational hill town has returned to a farming area and summer visitor economy. Being rural, dogs are a part of the day-to-day scene, and are often seen working on the farms.


While Chesterfield has no veterinarians, there are three nearby in Williamsburg, just six miles away. Within the town of Chesterfield there are several parks and trails that make for dog-tastic opportunities for a lively walk. Krug Sugerbrush State Forest offers great swimming, shaded picnic spots and enough space to bring your family tribe to relax and enjoy the trails and views of the Connecticut River Valley.

Walk the Chesterfield Gorge trail for dramatic rock formations or the easier pathway down River Road to George Bliss Park.


Neighboring communities offer plenty of park and camping adventures where you and your pup can relax and enjoy the serenity and beauty of Chesterfield.

Best Dog Neighborhoods in Chesterfield, MA

  1. Dog Parks 0
    Population Density 1,162/sq mi

    #1 Chesterfield

    This community has one gorgeous neighborhood referred to as Chesterfield. Chesterfield Gorge is a nature reserve of deep canyons with a wag-tastic half-mile trail along the cliff top that offers views of the gorge. The East Branch Trail at Gilbert Bliss State Forest is a 9-mile trail one way with rolling terrain and short climbs and descents. Krug Sugarbrush State Forest offers 15 miles of mixed use trails for pawsome walks with your pup. The Dead Branch State Forest also offers sniff-tastic walks among some of the unusual fauna and small wildlife. Fido is welcome in the parks and forests on leash.
    Dog neighborhood?
  2. Dog Parks 0
    Population Density 1,102/sq mi

    #2 Goshen


    This single neighborhood community in Goshen is the home of Hammond Pond Park and is just over two miles from Chesterfield. This beautiful park with gentle walking trails will have your pooch “waggin’ like he means it.” Rough it at Waterfront Camp which is available through Airbnb, and enjoy the beautiful, quiet and clean lake just perfect for a pawsome swim in the warm spring and summer water. Enjoy a walk around Damon Pond as the snow begins to melt as you and your leashed pup enjoy a trek across the small bridges to the sounds of babbling water as it runs over the rocks below.

    Dog neighborhood?
  3. Dog Parks 0
    Population Density 1,149/sq mi

    #3 Middlefield


    Glendale Waterfalls located in Middlefield just over 20 miles from Chesterfield. The Falls was once the site of a 19th century mill and antique remains can still be seen at the top. Further down the falls you can find the old grist wheel, once used for grinding grain and corn, laying on its side. A well-groomed trail is a great stroll to the bottom of the falls where you and your pup will find a beautiful swimming hole. You and your pooch can always find places to sit in the falls and let the water cascade over you during the warmer months.

    Dog neighborhood?
  4. Dog Parks 1
    Population Density 1,569/sq mi

    #4 Westhampton


    Fifteen miles from Chesterfield, is the small community of Westhampton. Located here is Springfield/Northampton KOA Campground, formerly called Windy Acres Family Campground, that has wooded and open grassy campsites with water and electricity. Your leashed pup will enjoy exploring the wide-open spaces and woods found within the campground. The fishing pond is a sniff-tastic exploration as the two of you wander the beach or wade in to enjoy the cool clear water. Plenty of picnic facilities are available to enjoy outdoor dining; check out the farmers market just around the corner. Your pup will enjoy some off-leash time in the Kamp K9 Off-Leash Dog Park.

    Dog neighborhood?
  5. Dog Parks 1
    Population Density 3,717/sq mi

    #5 North Farms/ Leeds


    Just under 25 minutes away in Northampton, Look Memorial Park is waiting for your pup. This 150-acre park is a great place to explore. The park has an array of shelters that can be reserved for group activities, and plenty of single picnic sites with grills and tables that can also be reserved. You and your pup will love the 1.2-mile walking path through covered bridges and along Willow Lake as you enjoy the scenic beauty of the park. Enjoy a rest on one of the benches along the way or check out the pedal boats at the lake. A steamer train, water spray park and a zoo will delight every member of your family.

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