Dog walking in Chesterton

Book on demand and scheduled walks with local dog walkers

How it works

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Flexible scheduling

Select the date and time that best suit your needs. Want a walk ASAP? We’ve got you covered.

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Customized for your pup

Choose between a 20-minute, 30-minute, or 60-minute stroll for your dog.

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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

Tina LChesterton, IN 46304

5.0

(92)

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Hi All! My name is Tina. I have several years of caring for dogs both personally and professionally and am an avid rescuer. I am available for walks and sitting and have experience with all types of breeds and special needs, such as working with older dogs and administering medications. I look forward to meeting you and will treat your pups like family!

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Katelyn LChesterton, IN 46304

5.0

(45)

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I can provide great long walks for all your fur children! I love to care for animals because of the immense amount of love they give you. I have been around animals my whole life, and currently have two female Chihuahuas that I love! I am here for all of your pet walking and watching needs!

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Socially Distanced Pet Care

Specialties

Fast walker

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!

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Socially Distanced Pet Care

Specialties

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

Miranda RChesterton, IN 46304

5.0

(15)

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I'm Miranda, and I'm super excited to be walking with Wag! I'm working as a middle school science teacher and I'm currently off for summer break. I love pretty much all animals, and I volunteered walking dogs with a shelter when I was younger. I had 2 awesome dogs at home growing up, and can't wait to adopt one when I get married in September! Thanks for letting me hang out with your pup!

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Melissa MChesterton, IN 46304

4.9

(196)

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Thank you for taking the time to view my profile. I am a nurse who loves the burn off some stress by taking care of animals. My favorite part of the day is getting to go for a walk. I'm hoping that will be your dogs favorite part of the day as well. I own and American Bully and have recently had the passing of our shitzu. I have over 100 walks under my belt and have had the pleasure of meeting so many sweet pups! Looking forward to meeting your sweetie!

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Joseph OChesterton, IN 46304

4.9

(174)

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Hello, my name is Joseph Orosz. I am 27 years old and I am an absolute dog-lover. I walked dogs for a company in Chicago for seven months and I look forward to continuing that here in Saint Paul. I believe that dogs are without a doubt humans best friends, and they should be treated as such. Love, warmth, understanding and patience are the qualities I will bring with me to each walk, and I will get to know each one as I go along. I look forward to meeting all sorts of new and wonderful pups!

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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!

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Top Pet Caregiver

Socially Distanced Pet Care

Specialties

Can run with dogs, Senior dog care, High energy dogs, Fast walker, Dogs who pull, Puppy care, Potty training, Puppy training

Sandra OChesterton, IN 46304

4.9

(63)

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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!

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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, Fast walker, Dogs who pull, Puppy care

Kimberly CChesterton, IN 46304

4.9

(50)

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Hi my name is Kim, I was lucky enough to have parents who loved animals, so my whole life I've had a love for dogs. I have adopted everyone of my dogs from shelters & have donated when I can. I've boarded friends & family dogs in the past while they were on vacation, or during emergencies. I had to break up dog fights in the past with either a blanket, water, or picking up their two back legs. Thankfully I've been able to stop it quickly. I've also been there twice, when my own dog had her litters. I treat them as if they were children, always putting their needs first. I'm looking forward for the rest of my life being blessed with animals.

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Whitney FChesterton, IN 46304

4.9

(36)

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Hi, I’m Whitney! I have grown up with dogs my entire life. I grew up with a huge and loving Weimaraner and a cute little Shih Tzu. Now that I am 22 and living on my own, I have three! My babies are Mini Poodle, Shih Tzu, and a Pitbull. They are so loving! Nothing cheers me up more than coming home from a long day at work than being greeted with kisses and wagging tails. I would love to keep your pet healthy and happy as I do mine! I will treat your dog as if it was my own and I will ensure you that you will not regret choosing me from Wag! to walk your pup!!

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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.