Dog Walkers in Chesterton

Find trusted dog walkers near you.

How Wag! Works

Book a Dog Walk with One of our Trusted Wag! Walkers
Track your Dog's Walk with our Live GPS Tracker
Receive Custom Reports Detailing your Dog's Activity

Vetted Walker Trust & Safety

Thoroughly Vetted
Wag! Guaranteed

Dog Areas in Chesterton

6 Parks
18 Shops
20 Eateries
2 Groomers

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

  1. Dog Parks 0
    Population Density 429/sq mi

    #1 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.

    Dog neighborhood?
  2. Dog Parks 0
    Population Density 429/sq mi

    #2 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!
    Dog neighborhood?
  3. Dog Parks 0
    Population Density 429/sq mi

    #3 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!
    Dog neighborhood?
  4. Dog Parks 0
    Population Density 429/sq mi

    #4 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.
    Dog neighborhood?
  5. Dog Parks 0
    Population Density 429/sq mi

    #5 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.
    Dog neighborhood?
Book me a walkiee?
Sketch of smiling australian shepherd