Dog Walking in Westchester Gardens, Madison, WI
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Westchester Gardens dog walkers
“Laura has been absolutely phenomenal with the weekly recurring dog walks. She gained the trust of our skeptical Bernese mountain dog immediately, and of course our golden loves her. Highly recommend!”
“10/10 Tucker loves going for walks with Autumn! He's such a good boy for her and is always really sleepy when he gets back. I will be rebooking with her again soon!”

“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!”

“Jilly is the best of the best. Peanut loves her and she put my mind at ease while I was at work knowing that Peanut was still getting love and attention. She sent super detailed notes and tons of pictures and videos. She was extremely communicative. I wish I could bring her with since we are moving! We will miss her!!!”
“Logan is dependable, trustworthy, and knowledgeable about dogs! My dogs are pretty crazy and Logan handles both of them wonderfully…I can notice they listen to me better since Logan has been caring for them. His wife is just as awesome and sometimes covers or comes with.”

About: I have been helping care for dogs both personally and as a friend since middle school. I began walking my own dog for an allowance in elementary school and loved it so I began to walk dogs for neighbors and family friends in middle school. Since then I have continued to work with dogs helping friends and family complete basic training (Sit, Stay, Lay, Leave it) and continued to learn more about dog behavior, activity needs by breed and body language. When walking your dog you can expect a minimum of a 1 mile walk/at least 20 minutes of actual walking time (or less if requested due to animal's health and abilities). I will ensure your dog is able to take in the sights and smells along the way and is engaged mentally to get some energy out. I work from home and am pretty flexible around my workday meetings. I have regularly scheduled reoccurring meetings from 9-930 on Mondays and Wednesdays but am flexible otherwise. When caring for your pet in your home you are the boss. I will follow any rules, routines or boundaries expressed by you and agreed to by me. Additionally, I will be respectful of your pet and your space. This means monitoring and respecting their behaviors and body language, keeping a clean space in your home, cleaning any mess made by feeding your animal, and cleaning accidents they may have had if provided the needed tools and supplies. When walking your dog you can expect a minimum of a 1 mile walk/at least 20 minutes of actual walking time (or less if requested due to animal's health and abilities). I will ensure your dog is able to take in the sights and smells along the way and is engaged mentally to get some energy out.
About: As many other animal-lover's, I have had animals in my life ever since I was born. My very first pet was a black cat named Korn that my parents adopted right before having me! Ever since I have never been without animals in my life. I'm knowledgeable in care for cats, dogs, reptiles and other herps, fish, birds, and horses. I personally have two German Shepherds, a cat, and crested geckos. My dogs I got as puppies and trained them with my mother, so puppy duties are easy for me too! Additionally, I used to work as an adoption manager and took care of two facilities that specifically adopted out cats, so I've worked with many different kinds of cats of different ages and disabilities. I have a plethora of experience with many different species and breeds of those species! My schedule is completely open and flexible. I'm able to be molded into your schedule as you need it! Some Saturday's or Sunday's I will be vending at fairs, but they're not often and only a few hours during the one day! I take care of my own animals whenever I am home. I have two german shepherds, one cat, and crested geckos. The mammals in the house all have the same food schedule. My dogs get lots of outside and inside playtime with me and each other! I love playing with Eva too, and she is big into snuggles (drool city when petting her). I also have crested geckos and have their own personal schedule I attend to (feeding 2-3x a week, watering daily, handling the young ones to get them adjusted to human touch.
“Anna is wonderful with our dogs! She always goes above and beyond and takes great care of them - and sends lots of cute pictures! Both of our dogs are reactive and she manages their antics well, and we always feel safe leaving them in her care. I can't recommend Anna highly enough!”

About: I have taken care of multiple different breeds of dogs! Small, medium and large! I also have experience with farm animals as well horses, cattle, goats etc. I’ve also had house with combinations of dogs, cats and horses. I’ve also had experience with epileptic dogs as well and having to give medication to pets as well. Although I do not have my own when I am house sitting I make sure to schedule my personal life around the pets I am watching. When pet sitting the pets I am watching are my number one priority. My work schedule during the week I typical work 8-9 hours a day and on the weekends I work I typically work 10-11 hours days. Even with working if the pet requires walks I will make sure they are getting the exercise they need before and after work regardless of the time. I am a very trustworthy pet sitter I have clients that are okay with friends or significant others coming over and I have others who are not, either way I fully respect that clients choice. I always make sure to clean up after myself and make sure the house is clean before leaving. When it comes to the animal I will not push the animal to do anything it does not want to do like going for a car ride, or anything else that may make the pet nervous. I do like to meet the animal and pet parents before hand just to make sure we have a good connection and trust.
About: As a passionate and experienced dog sitter, I bring over 5 years of pet-sitting experience and 4 years of hands-on care with my own pup, who I adopted as a puppy and has grown into a playful, loving companion. He’s wonderful with other dogs and children, which means your furry friend will have a built-in buddy during their stay! I provide a fun, safe, and loving environment for dogs of all sizes and temperaments. I live in a dog-friendly apartment just 2 miles from a spacious dog park where I frequently take dogs for exercise and playtime. Whether it’s walks, runs, car rides, or simply cuddling on the couch, your pet will receive plenty of attention, affection, and activity while in my care. I’ve also volunteered at the Humane Society in Green Bay during college, where I gained valuable experience working with dogs of all breeds and energy levels. I pride myself on being active, attentive, and highly dependable. When your dog is with me, they’re not just being watched—they’re being cared for like family. If you’re looking for someone who will treat your pup like their own, provide regular updates, and ensure they feel right at home, I’d love to be that person. Feel free to reach out with any questions—I can’t wait to meet your best friend! I work part time monday - thursday and my boyfriend starts work later in the day so my pup usually is only home alone for 5 hours out of the day and I come home during my breaks. I usually take him potty and feed him at that time and allow for some play time before going back My puppy loves running. He is a high-energy dog so we do walks and he has lots of toys to play with. We also have a balcony so we like to people watch together in the mornings ! If your dog is not into other dogs or high energy, my pup is also crate trained.
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. 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 quite shocking and stressful to them. I try not change their lifestyle too much while the parent is gone
About: My name is Raven, and I am an energetic and passionate lover of animals of all kinds. I grew up in a household wherein my mom saved any animal she could get her hands on, therefore I learned how to care for cats, dogs & even snakes very early in life. Ive worked for shelters since I was a pre-teen, both in volunteer and employment capacity, as well as being on Rover for almost 5 years now, and have fallen in love with every pet i've been able to care for. I'm respectful of your home, time and routine. I'm able to meld to any feeding, walking, cuddling time your animal is used to, as to not change their routine while you're away. I hope to meet you and your furry friend! I am a student at MATC, as well as working part time for Fedex. My schedule is very flexible, and I prioritize your pets before anything else. Rover is something i've cherished for many years, allowing me an opportunity to connect with families who need help, and spend therapeutic time with the animals who make them whole! I can give myself an immense amount of credit for being a very trustworthy person. I was taught by my father to leave things better than I found them, and enjoy cleaning and maintaining my own environment as well as yours. I've never had a complaint about my respect for my clients space. You may occasionally check your home cameras and find me having a conversation with your pets, but other than that, I am fully sane! As for boarding in my home, I am unable to care for dogs in my home as I have 2 cats without experience with dogs, and the number one priority in my care is safety. However, I can board cats as my cats are very comfortable and used to living in a multi-cat home.
About: I have been in the vet med field for about 7 years. During this time I have acquired many skills from that would set me apart from many other sitters. Hello everyone! I live a few minutes from Sun Prairie and additionally work in SP. I am typically available after working hours or on lunch breaks if you are located near me! ** I do not stay the night nor are pets allowed at my house (my cats do not like dogs) I am available for walks, potty breaks, meals/medications, and nail trims, at your request.
About: I have always loved animals no matter what kind. Our family rescues animals as well and finds good homes for them. Pets are like family and I treat all fur babies like my own child :) I have a lot of experience with larger dogs who dont walk so nice in leashes also. I love cats too and if they need love and affection I'm the perfect one. I would love to take care of you're fur baby for you while you are away at work or on vacation or just dont have the time. I will also go swimming with them or whatever you would like me to do with them. No rollerblading though is the only thing I will not do with dogs.
Loving dog walkers in your neighborhood
Search Results
Laura S.Star Sitter
“Laura has been absolutely phenomenal with the weekly recurring dog walks. She gained the trust of our skeptical Bernese mountain dog immediately, and of course our golden loves her. Highly recommend!”
Autumn H.Star Sitter

“10/10 Tucker loves going for walks with Autumn! He's such a good boy for her and is always really sleepy when he gets back. I will be rebooking with her again soon!”
Kathryn N.Star Sitter

“Lynelle was very patient, responsive, and caring towards our puppy. She was also quick to respond to our messages. Highly recommend! Thank you! 😊”
Ernst G.

“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!”
Jilly D.
“Jilly is the best of the best. Peanut loves her and she put my mind at ease while I was at work knowing that Peanut was still getting love and attention. She sent super detailed notes and tons of pictures and videos. She was extremely communicative. I wish I could bring her with since we are moving! We will miss her!!!”
Natalee Y.

“Natalee is very kind and conscientious, both to us and our pets. She takes great care of them, and they are always excited to see her!”
Logan M.

“Logan is dependable, trustworthy, and knowledgeable about dogs! My dogs are pretty crazy and Logan handles both of them wonderfully…I can notice they listen to me better since Logan has been caring for them. His wife is just as awesome and sometimes covers or comes with.”
TAYLOR P.
“Taylor is amazing with our dog. Our dog is so excited to see and be walked by taylor. Taylor communicates well when it comes to checking in on our dog. She is our number one choice for dog walking and sitting.”
Salem E.
“Salem has strong protective and nurturing instincts when it comes to animals! He also has a great breadth of knowledge of exotic animals and less common pets including reptiles, horses, fish, and insects. You can trust that Salem will treat your animals with great care and responsibility as if they were his own.”
Kate C.

“Kate was so patient and friendly! She has experience with reactive dogs and my Aussie warmed up to her extremely fast! After their walk he was happy and tired ?”
Stacy S.Star Sitter

“Stacy was great! She was communicative and she listened to all the details about my dog. She is timely and trustworthy, and my dog loves her too!”
Anna S.

“Anna was on time, very friendly and patient with our pups. She’s kind and positive and they’ll be her friends in no time.”
Anna S.
Star Sitter

“Anna is wonderful with our dogs! She always goes above and beyond and takes great care of them - and sends lots of cute pictures! Both of our dogs are reactive and she manages their antics well, and we always feel safe leaving them in her care. I can't recommend Anna highly enough!”
Kirsten R.
“Kirsten is an excellent dog sitter for our family when we are out of town! She is affordable, cleanly and always sends wonderful updates on the dogs. She does a great job with whatever you ask of her! We highly recommend her!”
Tatiana C.
About: As a passionate and experienced dog sitter, I bring over 5 years of pet-sitting experience and 4 years of hands-on care with my own pup, who I adopted as a puppy and has grown into a playful, loving companion. He’s wonderful with other dogs and children, which means your furry friend will have a built-in buddy during their stay! I provide a fun, safe, and loving environment for dogs of all sizes and temperaments. I live in a dog-friendly apartment just 2 miles from a spacious dog park where I frequently take dogs for exercise and playtime. Whether it’s walks, runs, car rides, or simply cuddling on the couch, your pet will receive plenty of attention, affection, and activity while in my care. I’ve also volunteered at the Humane Society in Green Bay during college, where I gained valuable experience working with dogs of all breeds and energy levels. I pride myself on being active, attentive, and highly dependable. When your dog is with me, they’re not just being watched—they’re being cared for like family. If you’re looking for someone who will treat your pup like their own, provide regular updates, and ensure they feel right at home, I’d love to be that person. Feel free to reach out with any questions—I can’t wait to meet your best friend! I work part time monday - thursday and my boyfriend starts work later in the day so my pup usually is only home alone for 5 hours out of the day and I come home during my breaks. I usually take him potty and feed him at that time and allow for some play time before going back My puppy loves running. He is a high-energy dog so we do walks and he has lots of toys to play with. We also have a balcony so we like to people watch together in the mornings ! If your dog is not into other dogs or high energy, my pup is also crate trained.
Cassandra B.Star Sitter
“Cassie is an amazing pet sitter. She has been watch my two kitties for over 6 years now and needless to say they love her. Cassie is reliable and will care for your pets like they are her own. She has administered medication to my cats, stayed multiple nights with them, plays with them, and follows all feeding instructions perfectly! She will give you daily updates and sends pictures too! You couldn’t find a better person to watch your pets.”
Jackie G.

“Thanks much for the help on short notice! Ill call again in the future ?”
Raven H.
About: My name is Raven, and I am an energetic and passionate lover of animals of all kinds. I grew up in a household wherein my mom saved any animal she could get her hands on, therefore I learned how to care for cats, dogs & even snakes very early in life. Ive worked for shelters since I was a pre-teen, both in volunteer and employment capacity, as well as being on Rover for almost 5 years now, and have fallen in love with every pet i've been able to care for. I'm respectful of your home, time and routine. I'm able to meld to any feeding, walking, cuddling time your animal is used to, as to not change their routine while you're away. I hope to meet you and your furry friend! I am a student at MATC, as well as working part time for Fedex. My schedule is very flexible, and I prioritize your pets before anything else. Rover is something i've cherished for many years, allowing me an opportunity to connect with families who need help, and spend therapeutic time with the animals who make them whole! I can give myself an immense amount of credit for being a very trustworthy person. I was taught by my father to leave things better than I found them, and enjoy cleaning and maintaining my own environment as well as yours. I've never had a complaint about my respect for my clients space. You may occasionally check your home cameras and find me having a conversation with your pets, but other than that, I am fully sane! As for boarding in my home, I am unable to care for dogs in my home as I have 2 cats without experience with dogs, and the number one priority in my care is safety. However, I can board cats as my cats are very comfortable and used to living in a multi-cat home.
Morgan B.
“Morgan is an exceptional caregiver to all my furry friends! She is great with both cats and dogs and is able to administer medication when needed. She is very responsible and I know my pets are in good hands with her! I highly recommend her to anyone with a four legged family member.”
Sara C.
About: I have always loved animals no matter what kind. Our family rescues animals as well and finds good homes for them. Pets are like family and I treat all fur babies like my own child :) I have a lot of experience with larger dogs who dont walk so nice in leashes also. I love cats too and if they need love and affection I'm the perfect one. I would love to take care of you're fur baby for you while you are away at work or on vacation or just dont have the time. I will also go swimming with them or whatever you would like me to do with them. No rollerblading though is the only thing I will not do with dogs.
Westchester Gardens dog parents share their Rover experiences
Kat is absolutely wonderful with my dog. My dog is elderly and in the last year had both of her "ACLs" replaced. Kat was happy to work with us on gradually increasing the length of walks, avoid pulling or pressure, and go at my dog's pace. I would recommend Kat to anyone looking for a dog walker or pet sitter.
We LOVE Nicole. She has a flexible schedule so when we have needed her in a pinch she is always available to help out. Our pup loves going on long walks and is always so excited to see her. She responds timely to requests and has great communication for how the walk went!

I chose Annemarie to walk my brothers dog. Afterwards He texted me the following: She just returned Ricky after about a 45 min walk. Ricky came back in a good mood. The walker, named AnnMarie, was both pleasant and cheerful. She is worth utilizing if needed again.

How Rover works

1. Search
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Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
3. Book & Pay
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The median cost per walk for dog walking in Westchester Gardens is $24
Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your dog walker has to cancel, we’ll work with you to find a new walker.
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We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
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 Westchester Gardens on Rover as of Aug 2025 was about $24 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.
Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, dog walkers on Rover respond in under an hour.
Experience can vary widely from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when comparing dog walkers available in Westchester Gardens.
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.













