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HomeDog Walking

Chesterfield, MA

Dog walking in Chesterfield

Book on-demand and scheduled walks with local dog walkers. Choose between a 20, 30, or 60-minute walk for your pup.

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How Wag! works

Easily find and book trusted Pet Caregivers near you

Pick a service

Pick a service

Whether it's Walks, Drop-Ins, Sittings, or Boardings, choose the service that best fits your pet's needs.

Choose your Caregiver

Choose your Caregiver

Select from committed Caregivers who understand your requirements. Chat directly to ensure the perfect match!

Follow along in the app

Follow along in the app

Download the Wag! App to track walks via GPS, communicate with your Caregiver, and enjoy real-time photo and video updates.

Rate and review

Rate and review

Share feedback to help other Pet Parents find their perfect Caregiver.

Wag! Guarantee - Pet caregiver with dog

Wag! Guarantee

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booking.

Trustworthy care

All Pet Caregivers are screened and background checked. All reviews are from verified Pet Parents.

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Customer reviews

Unable to take your dog on a walk today? Dog walkers through Wag! are available to care for your pup whenever you’re not. Every dog walker has passed an enhanced background check. Get photos and updates on where your dog poops and pees while you follow along via GPS in the app.

review
walk

Courtney was great! My dog has separation anxiety & is usually freaking out when I get home after being gone all day. But this time, she was calm and happy. She clearly loved Courtney!

Lauren G

review
sitting

Taylor was such an amazing sitter! She gave me detailed updates every time she checked in on the pups. Will definitely hire her again if she is available :)

Ivianna S

review
boarding

Yuki boarded at Mari’s house and she had a great time. She loves running in the background. Thank you so much for taking good care of Yuki.

Cari P

review
drop-in

Thank you for taking such great care of our kitties, so glad to hear that they were in good company while we were away!

Rebecca G

review
sitting

Keera was great with Archer and went at his pace! I got a ton of updates and Keera was super responsive and gave great updates! Keera was flexible when I was coming home sooner than expected.

Suzanne C

review
walk

Above and beyond service and communication! Would recommend time and time again! Extra caring and loving!

Lindsey B

review
boarding

Kristen took such great care of Mia while I was away for the weekend! Super responsive and easy to communicate with. Mia would love to stay with her again!

Nicole C

review
drop-in

Sheana came through when I was in a pinch. I needed someone to let the dogs out because I was stuck in traffic in the mountains. She responded last minute and had excellent communication. She’s the best!

Lindsay C

review
sitting

It was our first time leaving Skittles with a sitter, and Daniel did a great job of assuaging our fears! He was super communicative and made sure we knew that Skittles was in good hands. Highly recommend!

Christi B

review
drop-in

He looks so happy with you dropping by! Thank you so much for your loving caring attention. Love it!

Crystal C

review
boarding

Kelli was awesome boarding my two dogs. Not only did she give daily updates with videos and pictures she also worked with them on introducing them to her cat and getting used to her big dogs. Can't recommend enough!

Cody H

review
walk

Sara went above and beyond for us and our pet. Gave us some peace of mind while out of town and we couldn’t be more grateful. Def recommended!

Jenn S

Why book dog walker in Chesterfield

Busy Pet Parents sometimes need a hand when it comes to ensuring their pup is getting the potty breaks and exercise they need. That's where Wag! comes in! Local Chesterfield, MA dog walkers are background checked and registered on the Wag! platform, ready to take your dog on an adventure when you need them. Your dog can make a friend in the neighborhood, and you can re-book with the same dog walker easily in the app. Chesterfield, MA has "pawlenty" of parks and neighborhoods that your dog is itching to explore!

Why book with Wag!

The best dog friendly neighborhoods
in Chesterfield

Unable to take your dog on a walk today? Dog walkers through Wag! are available to care for your pup whenever you’re not. Every dog walker has passed an enhanced background check. Get photos and updates on where your dog poops and pees while you follow along via GPS in the app.

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Chesterfield

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.
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Goshen

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.


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Middlefield

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.


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Westhampton

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.


North Farms/ Leeds

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.


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