Chesterton, IN

Dog walking in Chesterton

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

Looking for other services? Book Sitting or Boarding with Wag!

Looking for other services? Book Sitting or Boarding with Wag!

How Wag! works

Easily find and book trusted Pet Caregivers near you

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

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

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

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

Wag! Guarantee

Peace of mind with every
booking.

Trustworthy care

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

Protected bookings

Every booking on Wag! is backed by up to $25,000 of coverage for your pet and your home.Learn more

Reliable communication

Photo and video updates, and in-app messaging to keep you connected during every service.

Assistance anytime

In-app and live support from Wag!’s Trust & Safety team, available when you need it.

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.

Thank you so much you are so kind

aymen O.

Jenna is the best! I won t even jog with my dog, but she will! He s going to start loving her more than me before long if she keeps spoiling him the way she does!

Kali N.

Jenna and Woofles love each other! Another perfect walk in the books. I appreciate her love and detail tending to my pup.

Kali N.

Thanks for taking great care of my pups on their walk

Jennifer S.

love jenna she loved my babies like they were hers plus go cubs ... how can you go wrong!

Amber H.

Jenna is the best! You can really tell they both enjoy each other s company! Woofles is a giant boy and we love how his strength doesn t phase her one bit and the thorough report cards. He already can t wait for next time s belly rubbins!

Kali N.

Jenna provided the cutest photo and a very thorough report of her time with my pup and you can tell they both enjoyed each others company! Will definitely prioritize Jenna for future walks. Thank you so much!

Kali N.

Jenna, you are so friendly and kind. I am so glad that anna was able to connect with you and had an amazing walk. Thank you for coming on this chilly day!

Jess M.

I was super nervous to let a stranger walk Dixie, but it s necessary. Shanie was great! She even taught me a few tricks for when Dixie is pulling.

Megan R.

Thank you!!

Lindsey H.

Why book dog walker in Chesterton

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 Chesterton, IN 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. Chesterton, IN has "pawlenty" of parks and neighborhoods that your dog is itching to explore!

The best dog friendly neighborhoods
in Chesterton

Historic Downtown

You can't talk about dog-friendly places in Chesterton without mentioning Thomas Centennial Park. Not only is this a furrific place to walk through history, but it also is the home of the local farmers market. Farmers markets are always lovely, especially when you can bring your dog along, but this one has a "bark in the park" section that sells pet food and pet treats! There are so many chances for belly rubs here that your dog won't be able to stop wagging his tail! There are even water bowls set out for your pup. You'll need to keep a leash on your pal while you're here and bring some waste baggies for those clean-ups.

Dune Acres

Dune Acres has an opportunity for you and your dog to do something that you may not be able to do anywhere else. The Dune Challenge is pawfect for pups and pooch parents who love to, well, challenge themselves! Check in at the front desk and choose your level. The casual level allows you to bring your dog with you to climb the dunes. It is a fun way to get some exercise, and if you complete it, you get a sticker. There is a more extreme challenge as well, but you can't bring your dog on that one. Make sure you bring a leash and water. Don't forget to check out the gift shop!

National Lakeshore

Indiana Dunes has many options for a day of fun in the sun. There is a dog-friendly beach, many dog-friendly trails, and even a few small dunes to climb. You are sure to have a furrific day here! There is a small fee to get in, so bring some pocket money. You'll have to have your dog on a leash when not in the water. Bring drinking water because there is no running water here. This is a popular site for picnics and family gatherings, so come ready to spend the entire day. The only thing this park is missing is a dog park!

Willow Creek

The Prairie Duneland Trail runs from Chesterton to Hobart. You can find an access point in Portage's Willow Creek neighborhood. The first two miles take you through the city but after that, you are led out of town and through the beautiful countryside. Most of the trail is paved, but there are some parts of the trail that still need to be improved. You and your dog can spend as little or as much time as you would like on the trail. Just remember that you do need to keep your dog on her leash at all times. Bring lots of water for the trail because there are few watering stations along the way.

Mccool Road

The Iron Horse Trail is the trail that runs from Chesterton to Portage. It is a two-mile trail that is paved most of the way. The trail ends in Imagination Glen Park. If you need a little more exercise, you can take a side trail to Woodland Park after you finish. Both parks are pet-friendly. There are leash laws for this area, though. Bring water with you because the restrooms do not allow pets to come in. Doggie waste bags can be found on some of the trash cans, but not all of them, so you might want to carry a few with you. This is a good hike that is easy to walk with your dog and your children.