Dog walking in Chesterfield

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

Stephanie WChesterfield, MA

5.0

(158)

Book now

“I’d love to walk your dog!”

Hello, my name is Stephanie. I'm an artist and I love animals, have since I was a kid. I've always been told that I am a calm, kind, patient and observant person. Because of that, I feel like it’s always been easy for me to understand animals and get along with them. I'm currently working with a group of animators to create a short animated film and studio. I've spent a bit too much time indoors lately, so I'd love to get out more, and to do it while walking a dog would be a big plus!

Background Checked

Top Pet Caregiver

Specialties

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

Emily CChesterfield, MA

5.0

(62)

Book now

Hello! My name is Emily and I'm currently studying to be a vet tech. I have extensive experience with dogs of all breeds, sizes, and personalities. I have helped out vets in the exam room, hired by close friends and family to walk dogs, and even walk dogs for my town shelter! Hope to meet you and your furry friend soon!

Background Checked

Top Pet Caregiver

Specialties

Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, High energy dogs, Training experience, Dogs who pull, Puppy care

Marley BChesterfield, MA

5.0

(32)

Book now

“You say “walk” and I say “how far? how long?””

I am a doctoral student with some extra time to commit to being healthy and active. Most humans are not available during the times of day that I am free, and so I hope to find some furry friends to accompany me on walks during the day. I love dogs for their dependability and companionship, and it is only fair that we humans show them the same respect. You can count on me to treat your friend with kindness and care, and to always be on time for them.

Background Checked

Top Pet Caregiver

Specialties

Can run with dogs, Oral medicine administration, Senior dog care, High energy dogs, Puppy care, Fast walker

Ruslan AChesterfield, MA

5.0

(24)

Book now

“A random act of kindness creates an endless ripple”

I am a high school graduate and a well known person in my city. I am a college student looking to have fun with some furry babies and kitties soon!!!! I can’t wait to meet my next new pup! I enjoy all animals and think of them as free therapy because they offer unconditional love!

Background Checked

Specialties

Can run with dogs, Oral medicine administration, Senior dog care, High energy dogs, Training experience, Dogs who pull, Puppy care, Fast walker

Alex HChesterfield, MA

5.0

(22)

Book now

Hi! My name is Alex and I believe that your dog deserves the best care possible. I’ve always had a dog and currently have a Yellow Lab named Charlotte and a Pitbull mix named Sasha. I’ve been caring for many dogs on and off for the past 5 years and love to meet new ones whenever I can.

Background Checked

Top Pet Caregiver

Specialties

Oral medicine administration, Senior dog care, High energy dogs, Training experience, Puppy care

Anne DChesterfield, MA

4.9

(70)

Book now

“Dogs and puppies and tail waggers, Oh My!!!”

Hi There! I’m Anne and I have been a dog owner and lover all my life. I don’t have a dog right now, so I’d love to be your dog’s new friend and give him/her the extra TLC needed when you’re away! I am a local teacher, so I come with great references and you will not be disappointed in my pet care. Thanks for considering me!!

Background Checked

Top Pet Caregiver

Specialties

Oral medicine administration, Senior dog care, Special needs dog care, Puppy care

Mason BChesterfield, MA

4.9

(56)

Book now

“Patient and energetic dog lover”

My name is Mason, and I live in Florence with my pit mix Beatrice. I adopted Bea when she was about two-years-old, anxious, and entirely unsocialized. Since then I have put countless hours into training and rehabilitating her, and that experience has given me the patience to look after other dogs as well. Bea has helped me become understanding and flexible with how I interact with all dogs, which makes walking and training them even more enjoyable. I look forward to meeting your furry friends!

Background Checked

Specialties

Can run with dogs, Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, High energy dogs, Training experience, Dogs who pull, Puppy care, Fast walker

Julia HChesterfield, MA

4.9

(30)

Book now

Hey, I'm Julia (pronounced who-Lee-Uh)! I've had dogs my whole life. With every glance at a dog, a willingness for bonding and trust is deeply embedded within my gaze. Sometimes, the sweet pup wants nothing to do with it and that is totally fine. My natural instinct is to convey my openness and availability. The unspoken is so beautiful! The non-verbal cues and boundaries that animals are able to communicate is never taken for granted when we're hanging out!

Background Checked

Specialties

High energy dogs, Fast walker

Lauren LChesterfield, MA

4.9

(17)

Book now

Hi, my name is Lauren and I am 24 years old. When I am not out and about, I love playing and taking my Shih Tzu, Oreo, for walks. Being around happy and playful dogs really brightens my days. I look forward to getting to know and love your dog, as well!

Background Checked

Lucia OChesterfield, MA

4.8

(23)

Book now

My name is Lucia, I am a person who loves dogs. I am in post grad and would love to walk your dog between classes! Please consider me as I love dogs of all types and love to go the extra mile.

Background Checked

Dog Walking in Chesterfield

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

Chesterfield

48
Population Density
1,162 per sq. mi.

Chesterfield

48

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.

Goshen

36
Population Density
1,102 per sq. mi.

Goshen

36

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.


Middlefield

24
Population Density
1,149 per sq. mi.

Middlefield

24

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.


Westhampton

12
Dog Parks
1 park

Population Density
1,569 per sq. mi.

Westhampton

12

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.


North Farms/ Leeds

0
Dog Parks
1 park

Population Density
3,717 per sq. mi.

North Farms/ Leeds

0

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.