Dog Walking in High Crossing, Madison, WI

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated High Crossing dog walkers

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Anna S.
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Anna S.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
17 reviews
5 repeat clients
3 years of experience
Madison, WI, 53714

Anna was wonderful! She was communicative from the start and respectful, gentle, and patient with my dog. He's nervous around new people, but he warmed up to her quickly. She walked him well, asked a lot of great questions, and looked for her after she left. Can't recommend Anna more!

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Melissa T.
Sitter Profile Image: Samantha S.
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Samantha S.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
26 reviews
10 repeat clients
25 years of experience
Madison, WI, 53704

Samantha was great! Showed up on time and took good care of Pico. He came home from his walk happy and ready to rest!

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Katie S.
Sitter Profile Image: Alissa W.
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Alissa W.
from
$14
per walk
10 years of experience
Ridgewood, Madison, WI, 53704

About: New to Rover, but NOT new to pet care! I have taken care of dogs, cats and other animals since I was 12 years old! I've had pets of all kinds for the past 10 years and I have also been hired to pet-sit for family, friends, and neighbors throughout middle school, high school and college! Additionally, my father owned a small dog walking business in our town while I was growing up, so I have lots of experience with walking all kinds of dogs. I am familiar with how to walk with and take care of dogs of all sizes from chihuahuas to great Danes! And I have experience working with varying ages, from puppies to older doggos who need additional care such as medication administration or walking accommodations. In addition to growing up with dogs, I've also had and taken care of cats, reptiles (lizards and turtles), rodents (hamsters, guinea pigs, rats & rabbits), and fish which gives me a wide range of drop-in visit expertise! I am familiar with how to clean liter boxes or small animal enclosures/cages, cleaning water fountains and food bowls, serving food and treats, administering medications, playing with your pet or using other forms of enrichment, etc. I am looking forward to working with you and your pet(s)! I am currently working part-time, so I have plenty of time to hangout with your pet(s)! I am generally available on weekdays from 8am-1pm and 6pm-11pm. My weekend availability fluctuates, but when I am in town I am available on Saturdays and Sundays from 11am-9pm! I currently offer dog walking and drop-in visits for dogs, cats or small animals. To ensure your pet gets the best from me, I make sure that I have detailed instructions about what your pet needs from my visit and/or walk. This includes having conversations about things like how much to feed them and when, litterbox changing specifics, changing your pets water, keeping your pets areas clean, any medication instructions you have for me, where you want me to walk your dog, expectations for waste disposal, or any other specific details I need from you in order to take care of your pet!

Sitter Profile Image: Kathryn N.
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Kathryn N.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
31 reviews
11 repeat clients
10 years of experience
McClellan Park, Madison, WI, 53718

Tofu has such a great time when Kathryn walks her! Kathryn is flexible and we always feel like Tofu is getting the same level of attention and care that we give her! Will definitely book again in the future

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Junko T.
Sitter Profile Image: Paul M.
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Paul M.
from
$15
per walk
9 years of experience
Madison, WI, 53718

About: I have 2 large rescues that have been a part of my family for the last 9 years. When I lived in apartments, I helped watch other neighbors' dogs and always enjoyed getting to know them and learn about their routines, hobbies, and quirks. While my family never had a dog growing up, I love being around them now and could never go back to a life without them! Since I work part time at a local farm, and am only just getting my own farm up and running, I have a relatively flexible schedule from week to week, especially during the winter, early spring, and late fall. I am thorough when it comes to taking care of my dogs' health and safety, as well as the health and safety of all pets that are in my care. I am always vigilant about traffic while walking dogs near any roads, and am always careful of walking them near other animals. When in another's home I am respectful of boundaries and rules and always clean up after myself or any messes that a pet may make.

Sitter Profile Image: Hailey R.
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Hailey R.
from
$15
per walk
5.0 out of 5 stars
2 reviews
2 repeat clients
9 years of experience
Sun Prairie, WI, 53590

About: What sets me apart is my dependable, loving care. I treat every dog like family, giving patient attention, walks, playtime, cuddles, and plenty of love. I work mornings in retail, leaving afternoons and evenings free. I enjoy being active, but always plan my schedule around pets to ensure consistent, loving care. I adapt to each pets needs. I grew up with cats and dogs, and provide walks, cuddles, space if needed, plus updates, photos, and lots of love, care, and attention.

Sitter Profile Image: Wystria C.
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Wystria C.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
9 years of experience
Ridgewood, Madison, WI, 53704

About: I started pet sitting at age 12. I’m comfortable with all animals from exotic to barnyard (ex. Horses, pigs, bearded dragons, wolf-dogs, fox, skunks, parrots and ferrets). I have had my dog for six years, and I recently took in a senior cat over the summer whom has adjusted flawlessly. I am a full time student and currently unemployed during my pregnancy journey. I spend most days at home, as most of my coursework is online. My pets are crate trained and respect boundaries. I also have baby gates for separation. I do not require crate training but it is extremely helpful if your pet is, so please let me know!

Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
20 reviews
4 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

Was great with Dexter. He can be nervous around new people. But she did great with him

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Olivia M.
Sitter Profile Image: Virginia V.
Verified Background Check
Virginia V.
from
$15
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
15 years of experience
Sun Prairie, WI, 53590

About: First time bookings with me you will receive $20 off! Use this promo code https://www.rover.com/sit/virgiv43216 Hello! Your dog will never be left alone as I work from home. They will receive lots of attention, walks and play time with me and with my dog, Athena. I only take one client at a time in order to ensure quality time and attention. Athena is a loving and well socialized 2 year old Siberian who loves to gently play and share her toys with other dogs. We look forward to your visit! I work from my home and we have a fully fenced in yard! I am available all day to care for my pets and yours. When your dog stays here at my home I will give them plenty of attention and love. They are allowed on the furniture and I have many toys, healthy treats, and games available to keep them occupied throughout the day. This is a great fit for pets that may need medication and timely dosing. I will care for your pet like they are my own!

Sitter Profile Image: Cassandra B.
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Cassandra B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
30 reviews
10 repeat clients
15 years of experience
Madison, WI, 53704

About: I have done petsitting (cats and dogs) for over 15 years. Usually for animals where I personally know the owners and have spent time with the animal to create a bond/relationship. I want to full disclose with new perspective pets parents: I have a full time, in-office job with the standard business hours, Monday through Friday. If that's not what you are looking for in a house sitter, I understand. If I had a pet of my own, I would ensure all their needs are met. As a petsitter, I would to ensure their animal's life doesn't change or I could make it better in some small way especially since their parent(s) is gone I stay at the animal's home to care for them so their life isn't different than what it usually is for them. Changing their environment can be quite shocking and stressful to them. I try not change their lifestyle too much while the parent is gone

Sitter Profile Image: KarLee B.
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KarLee B.
from
$13
per walk
5 years of experience
Madison, WI, 53704

About: I've taken care of my parents' dogs since I was young, making sure they were always feed and walked, and most importantly, had tons of playtime. I work full time Monday-Thursday, but my weekends are open for caring for all types of fluffy friends. I'm available mostly on Fridays and Saturdays (anytime) and Sundays (until 8pm). I plan to do visits to homes to take care of your fuzzy friends. Any instruction given will be followed, i.e. always on a leash outside or fenced in, whatever your preference is.

Sitter Profile Image: Lindsay B.
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Lindsay B.
from
$15
per walk
5.0 out of 5 stars
3 reviews
20 years of experience
McClellan Park, Madison, WI, 53718

About: I’ve dog-sat for aunts and uncles since I was 16! I love dogs of all sizes and breeds :) big dogs have a special place in my heart because I used to show bullmastiffs when I was a kid! I work 3-4 days a week depending on my schedule. And I’m going back to school this fall. I am trying to save some money for a very expensive treatment that I’ve been trying to avoid so I’m doing what I can to make a little extra! I love our neighborhood and love being outside so I figured this is the perfect way to do that! My husband and I bought our house last November. We have a fenced in yard and an 8 month old chocolate lab puppy who LOVES other dogs and any opportunity to play with them! She will bark on occasion and when that happens, we just bring her inside because we don’t like to disturb our neighbors. She is allowed on the furniture when we invite her up so we don’t mind if you dog likes the couch! I would have the same respect for your house as I do my own!

Sitter Profile Image: Brittany H.
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Brittany H.
from
$15
per walk
5.0 out of 5 stars
3 reviews
12 years of experience
Bluff Acres, Madison, WI, 53704

About: Hello! I was raised with dogs, and love spending time with them! I travel too often to have my own full time pet, so I would love to house or watch yours while you are traveling, and we can swap stories when you get back! I helped my family raise a puppy when we got her back in 2019 and still love spending time with her whenever I go home to visit. I work full time at home, so I have flexibility to take care of your pet when they need it most. Can’t wait to meet you furry besties! :) I work full time at home in IT, it’s mostly computer facing, so there’s a lot of flexibility throughout the day. I’m usually around for most of the weekend as well. I live right next to a walking path, and go for walks regularly. I have a fenced in yard for dogs to play in, as well as an extra cage if ever needed. I am the only person in the home, with no other animals, so my full attention will be for them only. I always check food and water bowls, and any other items they use daily.

Sitter Profile Image: Jackie G.
Verified Background Check
Jackie G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
51 reviews
15 repeat clients
20 years of experience
Madison, WI, 53718

Jackie is consistent and punctual she treats our lalu as her own takes good care of him and gives him a good walk. Lalu really looks forward to her walking him

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Leo B.
Sitter Profile Image: Mason H.
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Mason H.
from
$15
per walk
20 years of experience
Marquette, Madison, WI, 53704

About: I've lived alongside pets my whole life, and have volunteered for hundreds of hours at various animal shelters. I have experience with both dogs and cats of all sizes and ages. I also love long walks, beaches not required, and am perfect for those high energy dogs that never seem to tire out. I am a nurse working a swing shift so I am up at hours, on an ever-changing schedule. This means that I can care for your furry little ones on a short notice, and even check in on them at night if you are away. I only have a small apartment at the moment, unsuited for pets of my own or for yours. I will change this information as my circumstances change.

Sitter Profile Image: Ben G.
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Ben G.
from
$21
per walk
5.0 out of 5 stars
11 reviews
1 repeat client
35 years of experience
Madison, WI, 53718

Excellent service. He took care of our dogs like they were his own. I think they would have rather we stay on vacation and Ben come walk them. Will definitely use again.

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Rachel D.
Sitter Profile Image: Caden K.
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Caden K.
from
$15
per walk
17 years of experience
Madison, WI, 53704

About: Ive been taking care of my familys pets since I could walk When it was dinner time I fed them, or when it was time to go for a walk or go outside to use the bathroom I was right there, excited to help out. I do a lot of research into the pets I'm caring for to ensure I'm providing the best care possible I'm currently looking for work so I'll have plenty of time to hang out with your furry (or scaley) friends! I will update this once something changes. Im always learning new and better ways to care for animals. One of my favorite things is to research the animals and find out the best ways to care for them

Sitter Profile Image: Bobby K.
Verified Enhanced Background Check
Bobby K.
from
$15
per walk
5.0 out of 5 stars
11 reviews
3 repeat clients
32 years of experience
Heistand, Madison, WI, 53714

We were happy to have Bobby take care of our dog while we were away.

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Joel S.
Sitter Profile Image: Christine D.
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Christine D.
from
$15
per walk
4.8 out of 5 stars
21 reviews
7 repeat clients
10 years of experience
Cottage grove, WI, 53527

About: I always had a dog. The house isn’t a home if you don’t have a dog. Family brings there dog over. Every one gets along I’m working part time . Will have time to play and walk your dog. I care for dogs. I have a dog name Louie. We’re always outside I have a big fenced in yard . I have a dog so my house is dog proof. I have a one story house on a quiet street.

Sitter Profile Image: Ernst G.
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Ernst G.
from
$15
per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
15 years of experience
Monona, WI, 53716

Ernst is super friendly, responsive and knowledgeable. We have 70 lbs adolescent pup who has a lot of energy to give. Ernst is great at keeping our pup in line. I already notice an improvement in our pet’s loose leash walking!

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Sofia S.
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High Crossing dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Sylvia was great with our little shy doggie. She was patient & caring- taking the time to let or dog get used to her before they walked. No wonder she is a star sitter.

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Hex H.
Dog Walking
5.0 out of 5 stars

She's always so kind and great with my dog. Hes a stranger danger dog but he loved Anna immediately! She's very communicative and timely

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Melissa T.
Dog Walking
5.0 out of 5 stars

Since recently moving to Madison, I have been overjoyed to discover Alisha. She has become a lovely caregiver for my anxious rescue dog. Our partnership kicked off with a thorough meet-and-greet that instantly built trust, evolving into drop-in visits and dog-walking sessions, with overnight house-sitting on the horizon for future needs. Alisha's calm, nurturing demeanor is exactly what my dog needs, who has a challenging history of anxiety and trust issues. Alisha consistently shares reassuring photos alongside detailed updates, giving me peace of mind no matter how long I'm away. I would highly recommend Alisha to fellow dog owners, especially those with loving yet challenging pets that require extra patience and understanding. Hazel is forming a genuine bond with her, displaying real joy and relaxation in her presence—precisely what I hoped for—and I eagerly look forward to booking her services again.

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Sammy G.
Dog Walking
5.0 out of 5 stars

Jilly is amazing! My dog absolutely loves her, and she is so good about making sure that all of my pets have everything they need while I’m away.

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Lori A.
Dog Walking
5.0 out of 5 stars

Eileen has been very dependable and communicative! We love the peace of mind she brings our family and Raleigh loves getting out in the neighborhood while we are at work!

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Leslie S.
Dog Walking
5.0 out of 5 stars

Jimmy is a great match for our dog Tala! He sees her twice a week and provides her walks, playtime in the yard, and brings his dog so she has a doggy companion to play with. He has been patient and helpful working with Tala despite her having little training as a new rescue dog. We hope to have him as our regular walker for a long time!

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Meagan S.
Dog Walking
5.0 out of 5 stars

Thank you for taking care of Clementine’s walk tonight on such short notice. She was tired and happy when I got home.

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Shana H.
Dog Walking
5.0 out of 5 stars

We love Tina and our dog Stevie loves her even more! We use her often for check-ins and walks. She goes above and beyond with communication and photos. Appreciate having her in our life to love on our dog.

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Jessyca A.
Dog Walking
5.0 out of 5 stars

Laura came and met us before starting walks with my dog, Ruby. She was great with Ruby and very attentive to her. The first time Laura came to walk Ruby, Ruby was shy and uncertain. Laura was patient and slowly allowed my pup to warm up to her so they could play in the yard. I highly recommend Laura, she clearly loves animals and does a great job recognizing what they need and goes at their pace.

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Natalie P.
Dog Walking
5.0 out of 5 stars

Logan and Brittney are simply the BEST! They are extremely vigilant and notice any small change in behavior and/or health. They tidy up and take care of any unexpected messes. They are dependable, compassionate, and very knowledgeable about dogs.

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Patricia W.
Dog Walking
5.0 out of 5 stars

Helped out immensely when I decided to take a last minute trip, very attentive and flexible care, greatly appreciated.

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Wystria C.
Dog Walking
5.0 out of 5 stars

We always love when Tonisha comes to walk our dog! She always takes great care of her, and our pup loves her walks with her!

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Kylee S.
Dog Walking
5.0 out of 5 stars

Thanks for caring for our pups Molly! Great communication and care- I’d definitely book with you again.

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Tonisha A.
Dog Walking
5.0 out of 5 stars

Avery walks my babies every S/M/W and my girls adore her sooo much!!! I hope she likes my babies enough to walk them forever! She’s such a blessing and I wish she would never move 😭😭 please help me in keeping Avery where she currently lives rover 😊

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Heather L.
Dog Walking
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The median cost per walk for dog walking in High Crossing is $20

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Sitters in High Crossing average 2
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in High Crossing on Rover as of Feb 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a High Crossing dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 89% of High Crossing dog walkers respond in under an hour.

Dog walkers with repeat customers have an average of 2 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in High Crossing.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.