Dog Walking Woodland Way

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

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Woodland Way, Find top rated dog walking

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: Matthew P.
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Matthew P.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
43 reviews
11 repeat clients
8 years of experience
Middletown, MD, 21769

Matt is very dependable and communicates very well on every walk he takes Bella on. I know I can rely on him to take care of my baby while I am away every time.🐾

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Shawna H.
Sitter Profile Image: Abigail T.
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Abigail T.
from
$25
per walk
5.0 out of 5 stars
15 reviews
3 repeat clients
7 years of experience
Myersville, MD, 21773

Abigail has been walking my dogs for a while now. She always does an awesome job and is really good about sending pictures and details about the walk and my dogs always look happy in the pictures she sends. I would 100% recommend her to anyone because I know that they are safe with her. Thanks, Abigail!

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Ryan T.
Sitter Profile Image: Emily B.
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Emily B.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
70 reviews
31 repeat clients
30 years of experience
Middletown, MD, 21769

About: With over 30 years of pet care experience growing up on a small farm, I’ve had the privilege of caring for a wide variety of animals—from dogs and cats to livestock. My experience has given me a deep understanding of animal behavior, health, and care needs. Living on 100 acres, I offer a unique environment where pets have plenty of space to explore and play in a safe, supervised setting. Unlike many sitters, dog sitting is my main source of income, which means I am fully dedicated to giving your pet my full attention, love, and care. Whether it’s puppy training, senior pet care, or just providing lots of love and exercise, I treat every pet like they’re my own! *I also offer a contactless pet drop-offs and pick-ups if needed for early morning/late evening pick ups(+$fee per dog). You can drop your fur baby off in my outdoor kennel, text me and I will be sure to come get you pup as soon as I can and move them inside or to the fenced in area! I prefer to do this after we have met in person at least once to show you the kennel drop off/pick up. Pet care is at the heart of my daily routine. As a full-time pet sitter living on 100 acres, my day revolves around providing attentive, personalized care. From morning walks and playtime to feeding, grooming, and cuddling, I ensure every pet gets the love, exercise, and attention they deserve. Since pet sitting is my main source of income, I have the flexibility and time to accommodate individual needs—whether it’s extra potty breaks, medication schedules, or play sessions. Your pet’s happiness and well-being are my top priority every single day. There isn't an option to mark for older kids, Rover considers under 12yrs a child. I have a teenager and my youngest is about to turn 12. They have been raised around dogs and cats their entire lives, also my kids and our cats have their own side of the house that is gated off from all dogs. We have some outside barn cats that are used to running and hiding from our own dog Nala. It's ok if your dog doesn't like cats-they are very good at avoiding cars and dogs. I provide a safe, comfortable, and fun environment for all pets in my care. My property includes a fenced-in area detached from the house, allowing for secure, off-leash playtime where pets can run, explore, and enjoy fresh air safely. In addition to regular walks and exercise, I also offer bathing services, with pricing based on breed and size. My priority is ensuring each pet feels loved, comfortable, and well-cared for—whether they’re getting their zoomies out in the fenced area or enjoying a calm, cozy space indoors. Please make sure fur baby is up to date on all their vaccinations, flea and tick meds.

Sitter Profile Image: Brittany H.
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Brittany H.
from
$20
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
20 years of experience
Middletown, MD, 21769

About: I've owned and watched dogs since I was 10 years old. From small puppies, elderly dogs, to dogs huge as a mastiff and small as a chihuahua. Whether they be my own, friends, or families I held dear, being around and caring for dogs have always been a huge part of my life! I've fed them, bathed them, given them medicine, and have always been relable. Currently, I am mostly self-employed & studying for a Real Estate license. I do work mornings at a horse barn, and have a contract gig working occasional weekends with a D&D-styled Bed & Breakfast. Thankfully those shifts are scheduled months in advance and, for barn work, typically wrap up around 11-Noon. :) I'm always willing to give dogs the ample affections and pets they need! I'm super attentive to when they need to go outside/take a walk, have their food right on schedule, have some playtime, or whenever they just geniunely need attention and love. I honestly do it everyday for my own dogs. So I'll have no trouble giving them the same needs I give my precious wee babies.

Sitter Profile Image: Ava O.
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Ava O.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
7 reviews
6 repeat clients
2 years of experience
Frederick, MD, 21702

Ava was really communicative and spent a lot of care looking after our pup. We will definitely be using her again!

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Neena T.
Sitter Profile Image: Leah H.
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Leah H.
from
$30
per walk
5.0 out of 5 stars
50 reviews
14 repeat clients
10 years of experience
Boonsboro, MD, 21713

We can’t thank Leah enough for dropping in on our pups for us. She spent time with all 3 and was careful to follow all instructions for our foster babies! We’ll definitely be having Leah watch them again in the future!!

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Jessica F.
Sitter Profile Image: Jacob D.
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Jacob D.
from
$20
per walk
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Hagerstown, MD, 21742

Jacob has been a wonderful dog walker for Zoey. He makes her walking experience enjoyable and makes over her and she just loves him. He's been very punctual and has walked the dog for the scheduled amount of time.

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Alicia M.
Sitter Profile Image: Dominika W.
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Dominika W.
from
$20
per walk
5.0 out of 5 stars
48 reviews
11 repeat clients
15 years of experience
Frederick, MD, 21769

Highly recommend Dominika. You can tell she is a dog lover and did great with both of my Chihuahuas who take some time to adjust to new people!

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Stephanie G.
Sitter Profile Image: Tiffany B.
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Tiffany B.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
27 reviews
12 repeat clients
17 years of experience
Boonsboro, MD, 21713

Tiffany took great care of our guy on her visit! Looking forward to hiring her again!

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Jess M.
Sitter Profile Image: Dominique M.
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Dominique M.
from
$22
per walk
5.0 out of 5 stars
135 reviews
28 repeat clients
6 years of experience
Frederick, MD, 21703

I am very pleased with Dominique! She is very friendly and polite and managed my two dogs very well. I definitely recommend her to anyone she will not disappoint.

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Katherine A.
Sitter Profile Image: Olivia P.
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Olivia P.
Star Sitter
from
$13
per walk
5.0 out of 5 stars
24 reviews
3 repeat clients
11 years of experience
Frederick, MD, 21703

About: I’ve taken care of dogs for as long as I can remember. I have grown up with dogs, and love all dogs. Neighbors and family members have relied on me to take care of their dogs. This includes feeding, exercising, medication and play time! I am experienced with handling puppies and with senior dogs as well. I currently don’t have any other commitments, so I have plenty of time to play and take care of your doggies! I’m available Sunday through Saturday all day and or night. I will follow set instructions if you have any in regards to being in your home. Otherwise, I will care for your beloved puppy like they are my own and use my judgment.

Sitter Profile Image: Arnaldo Z.
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Arnaldo Z.
from
$15
per walk
5.0 out of 5 stars
71 reviews
12 repeat clients
23 years of experience
Fairplay, MD, 21733

Arnie is terrific! He's always early, has a smile on his face, and comes prepared with poop bags! Very efficient and flexible. Arnie has been a God send. I'm glad I chose him to take care of Cannoli while I recovery from.surgery. highly recommend!

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Sherrie-Lynn H.
Sitter Profile Image: Brian B.
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Brian B.
from
$15
per walk
5.0 out of 5 stars
3 reviews
3 repeat clients
4 years of experience
Smithsburg, MD, 21783

Brian was reliable and he took great care of Pemi! We will definitely rebook with Brian next time we need help.

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Kyi-Sin T.
Sitter Profile Image: Amber G.
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Amber G.
Star Sitter
from
$15
per walk
4.8 out of 5 stars
62 reviews
34 repeat clients
17 years of experience
Hagerstown, MD, 21740

Amber was great. She communicated everything clearly, asked great questions and she and Winnie bonded immediately. I highly recommend Amber for dog walking!

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Margaret P.
Sitter Profile Image: Lauren M.
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Lauren M.
from
$15
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
2 years of experience
Frederick, MD, 21701

Lauren was a pleasure to work with and having her help was greatly appreciated and our pups enjoyed her visiting ! She's very responsive and takes in feedback very well! I would recommend her to others.

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Chris S.
Sitter Profile Image: Scott W.
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Scott W.
from
$15
per walk
25 years of experience
Myersville, MD, 21773

About: I've had dogs and cats for over 25 years and have trained many puppies and raised many rescue animals. Animals are like family to me and I've loved every one. Now that I have the time to help other animals, I'd love to help yours. I'm a retired Federal employee who is available in the morning or afternoon for pet check ins and walks. I live in the Myersville area and would be available to help in the surrounding vicinity. If you need a little space for your dog to run free, I have a fenced in yard with 2 friendly dogs. We usually take our dogs on walks and let them run in the fenced in area. I can walk your dog, check in on them, feed them, and let them out in your fenced yard.

Sitter Profile Image: Jaden B.
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Jaden B.
from
$15
per walk
15 years of experience
Hagerstown, MD, 21742

About: What sets me apart is the genuine love and care I have for every animal I meet! As a lifelong animal lover and pet owner myself, I understand that pets are family, and I treat them as if they were my own. I have experience caring for pets of all ages, from energetic puppies and kittens to senior pets who need extra patience, comfort, and attention. I’m comfortable adapting to each pet’s unique personality and routine, whether that means playtime and enrichment for younger pets or providing a calm, nurturing environment for older companions! I believe in building trust with both pets and their owners through reliability, communication, and compassionate care. I love getting to know each pet’s individual needs, favorite activities, and little quirks. Whether it’s sticking to a feeding schedule, administering extra TLC to anxious pets, or making sure your furry friend gets plenty of cuddles and playtime, I always go the extra mile!! My goal is to make every pet feel safe, loved, and spoiled while you’re away, giving you peace of mind knowing they’re in caring hands! As a lifelong animal lover and pet owner, caring for pets fits naturally into my daily routine! I currently have plenty of availability, allowing me to give each pet the time, love, and attention they deserve! In My Home: When caring for pets in my home, I strive to create a safe, loving, and stress-free environment where they can feel comfortable and secure. I follow each pet’s normal routine as closely as possible, including feeding schedules, potty breaks, exercise, playtime, and any special instructions provided by their owners! Pets in my care receive plenty of attention, affection, enrichment, and supervision. Whether your pet loves to play, cuddle, or simply relax, I make sure they feel right at home and are treated like part of the family! In Clients’ Homes: When caring for pets in their own homes, I understand how important it is to maintain consistency and respect their familiar environment. I carefully follow all instructions regarding feeding, medications (if needed), walks, playtime, and household routines to help pets feel comfortable while their owners are away. I provide regular updates, photos, and communication so pet parents can have peace of mind knowing their furry family members are happy and well cared for. My goal is always to ensure pets feel loved, safe, and cared for in the comfort of their own home!!

Sitter Profile Image: Shelby C.
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Shelby C.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
14 reviews
5 repeat clients
15 years of experience
Frederick, MD, 21701

We are so grateful to have found Shelby! It's such a relief to know that my pup is getting exercise and attention while I am at work all day. I highly recommend Shelby!

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Karen H.
Sitter Profile Image: Kaila M.
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Kaila M.
from
$20
per walk
5.0 out of 5 stars
12 reviews
4 repeat clients
9 years of experience
Frederick, MD, 21702

Kaila was terrific! She took good care of my dog, Tiny. She was responsive and gave me updates. I highly recommend her!

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Kendall G.
Sitter Profile Image: Ava C.
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Ava C.
from
$18
per walk
5.0 out of 5 stars
4 reviews
3 years of experience
Middletown, MD, 21769

Ava is very nice and timely. Daisy was tired from the long walk and play. I will definitely contact Ava again for walk and other Rover services.

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Maureen H.
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The median cost per walk for dog walking in Woodland Way is $20

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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer dog walking
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Sitters in Woodland Way average 3
repeat dog walking clients

FAQs for Dog Walking - Woodland Way

Frequently asked questions about Rover

As of June 2026, there are 2,237 sitters on Rover offering Dog Walking across Woodland Way. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Woodland Way. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Woodland Way.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

Yes, you can find walkers who have experience with handling special pet needs in Woodland Way. On Rover:

  • 90% of walkers can help with special care needs
  • 97% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

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