Dog walking in Chesterton

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

Joanna LChesterton, IN 46304

5.0

(19)

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“Care that makes a best friend”

Animals are my life. I have always had pets growing up as a child and my love for them has grown into my adulthood even more. I have a passion for learning and understanding all different types of animals. My experience in pet care is from having my own pets and caring for family, friends and volunteering over the years. I have recently started my own dog on behavioral training for a better understanding of his mind and learned so much that I feel I can also provide your dog!

Background Checked

Top Pet Caregiver

Specialties

Oral medicine administration, High energy dogs, Dogs who pull, Puppy care, Fast walker

Matthew MChesterton, IN 46304

5.0

(10)

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Hello! My name is Matt and I've been taking care of dogs for as long as I can remember! I've always been the first to volunteer to board friends’ and families dogs when they are away and even spent some time volunteering at PAWS, in Chicago, when I lived there. I believe dogs truly are a humans best friend and will be more than thrilled to walk your furry friend whenever you need! I can't wait to start working with you and your dog!

Background Checked

Specialties

Fast walker

Jason SChesterton, IN 46304

5.0

(3)

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I am a US Navy Veteran who is looking to walk dogs as a means to supplement the small income I receive from the VA once every month. I am great with dogs, and friendly with humans! Most importantly, I promise your pet will be treated with the same respect and attention I would give to my own dog (whom I love dearly). Available for last-minute walks and/or regularly scheduled appointments!

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Top Pet Caregiver

Leah SChesterton, IN 46304

4.9

(169)

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I am an animal lover and am a hardworking, caring, and responsible individual.I received my Master’s Degree from Northwestern & Bachelor’s Degree from Juilliard. I grew up on a small farm in Vermont where I had goats, chickens, dogs, cats, & rabbits. I learned at a very early age how to take care of animals and the dedication/hard work that is required to do so. I have a 7 year old min pin. I will do whatever it takes to ensure that your dog is well cared for and will go beyond what is expected.

Background Checked

High Demand

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

Michelle BChesterton, IN 46304

4.9

(89)

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“I <3 dogs!”

Hi I'm Michelle! I am an experienced dog walker and jogger (will jog with your dog upon request). I have experience with all types and sizes of dogs. I love meeting new dogs. Each dog is special and unique and I treat them as such. I am a marathon runner and avid weekend hiker. I will keep your pet healthy and happy. I will treat your dog with love and make sure your Wag experience is always positive!

Background Checked

High Demand

Top Pet Caregiver

Socially Distanced Pet Care

Specialties

Can run with dogs, Dogs who pull, Puppy care, Fast walker

Tyler TChesterton, IN 46304

4.9

(63)

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I've had my own dogs for almost my whole life. I have a chihuahua and a pitbull-boxer mix, so I love all kinds of dogs, sweet and feisty, small and large, shy and energetic. I have pet-sat for family and friends. While I am pet-sitting, I take them for walks to the park and around the neighborhood, feed them twice a day, give them treats, and play with them of course! You can count on me to make sure your dog is safe and has fun on our walks together.

Background Checked

High Demand

Specialties

Can run with dogs, High energy dogs, Dogs who pull

Sandra OChesterton, IN 46304

4.9

(62)

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“All dogs welcome!!”

Hello! My name is Sandra! I moved to the Chicago area from Michigan with my 14-years young, Jack Russell/Beagle mix, Kerby and my rescue mix Maggie. I have been dog sitting, walking, and playing since I was just 5 years old. I have experience with dogs of all sizes, personalities, and ages. I help out with my mom's dog, Max, who has hip dysplasia. I love to meet and hang out with new dogs and get to know each one's unique personality! I look forward to meeting and walking with your dog!

Background Checked

High Demand

Specialties

Dog first aid and/or CPR, Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, High energy dogs, Dogs who pull, Puppy care, Fast walker

Dog Walking in Chesterton

Chesterton, Indiana is quite the action-packed place. There are a ton of barktastic opportunities awaiting you here -- which makes sense, considering that the area was initially settled because it was a great place to farm and raise animals. The peaceful area also makes a family-friendly and fun-filled vacation spot. It's less than fifty miles from Chicago, which means you can relax in the countryside and be in the big city in an hour or so for the nightlife. It's the best of both worlds!

Coffee Creek Park is a beautiful little park where you can bring your whole family for a morning stroll. There are peaceful bridges over babbling brooks that make it look like it is out of a fairytale. There are many moms who bring toddlers here because it is such an easy walk. Sit real quietly, and you may even see a deer or two!

Looking for a park with more amenities? Chesterton Park is pawfect for those looking for a family park with plenty of activities! There are ball fields where the little leagues play, splash pads to get out of the heat, and walking trails that encompass it all. No matter what time of day you go, you are sure to find something to do and see. Just remember to bring your leash. 

Best Dog Neighborhoods in Chesterton

Historic Downtown

48
Population Density
429 per sq. mi.

Historic Downtown

48

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

36
Population Density
429 per sq. mi.

Dune Acres

36

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

24
Population Density
429 per sq. mi.

National Lakeshore

24

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

12
Population Density
429 per sq. mi.

Willow Creek

12

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

0
Population Density
429 per sq. mi.

Mccool Road

0

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.