Dog Walking Winchester

“Ryan is so great with our Pup that we keep increasing the requests and care for Abbie and making those bookings recurring. He always arrives with a pep in his step and is so attentive to Abbie. Thrilled to have discovered him.”

Rachel O.

“Corrine is a blessing. I injured myself and was unable to walk my pup, she responded to a last minute request, had her own supplies, and walked him far enough that when he came home, he was exactly how I like him to be, exhausted. I will definitely use her services again.”

Marchae C.

“Always amazing! Cheryl is a god send to me and Frank. I have hired her in the past for a walk here and there but with a recent break in my ankle I need help more now than ever and she has been wonderful! Not only do I recommend her, my Frank would too! He absolutely loves his walks with her!”

Bethany M.

“We absolutely love James! What really stood out to us is how much time he took to get to know our pup before even going on their first walk together. He didn’t just show up and clip the leash—he sat with her, probably learned her little quirks, asked questions, and made sure she felt comfortable and safe. That kind of care is rare, and it meant the world to us 💛 Highly, highly recommend!”

Alexandra V.

“Shawn is wonderful with our girl Apple! She is so kind, patient, and very trustworthy - we all immediately liked her and are so grateful that she can help us with our pup 😊”

Kevin L.

About: I’ve been around dogs my entire life and have experience caring for pets for family, friends, and neighbors. As a retired Division I student-athlete and current graduate student at Tufts, I am dependable, responsible, and highly organized. I understand that pets are family, and I treat every dog as if they were my own. One thing that sets me apart is my patience and ability to adapt to each dog’s unique personality. I have experience working with anxious, timid, and shy dogs who need extra reassurance, as well as high-energy dogs who thrive with exercise, structure, and play. As a former Division I athlete, I am also comfortable handling larger, stronger dogs and can confidently keep up with dogs that need long walks, runs, or plenty of activity. Whether your dog needs exercise, playtime, lots of attention, or simply a reliable person to check in on them, I’m happy to help. Your pet’s safety, comfort, and happiness will always be my top priorities. I also provide regular updates and photos so you can have peace of mind while you’re away. I’m a graduate student at Tufts University with a flexible schedule that allows me to provide reliable pet care throughout the week. I enjoy staying active and spending time outdoors, so dog walks fit naturally into my daily routine. Whether your pet needs a quick potty break, a long walk, or a drop in visit, I’m committed to being dependable, punctual, and responsive. Your pet’s safety and comfort are my top priorities. I take the time to learn each pet’s routine, personality, and specific needs so they feel secure and cared for while you’re away. I will always follow your instructions closely, keep pets safely leashed during walks, and provide regular updates and photos for peace of mind. I treat every home with respect and every pet as if they were my own.

About: Animals have been part of my life for as long as I can remember. I grew up surrounded by dogs, cats, birds, fish, turtles, hamsters, gerbils, and even chickens, and each one taught me something different about patience, joy, and unconditional love. Over the years, I’ve rescued dogs, helped others find their forever homes, and volunteered at shelters and adoption events. I have a soft spot for senior pets and pups with special needs. My dog Dumba is turning 16 this February, and supporting her through her golden years has taught me how to be gentle, attentive, and adaptable. Before Dumba, my dog Cookies bravely fought cancer for many months, and I cared for him through two surgeries and ongoing treatment. Because of experiences like these, I’m comfortable administering medication, monitoring health changes, and giving extra support to pets who need a little more care. I also love working with cats! Since rescuing Zoro when he was only 8 weeks old, I have developed experience with basic grooming, brushing, and keeping litter areas clean and comfortable. Your pets are family, and I’ll care for them with the same love, patience, and attention I give my own. My schedule is flexible, and I’m happy to accommodate your pet’s routine. I'm currently offering daily walks and drop‑in services. I live in Winchester and know the area well, so your dog can enjoy peaceful walks around Horn Pond or fun playtime at Sheepfold Dog Park. I share my home with my senior dog, Dumba, and my goofy cat, Zoro. They’re both used to being around other animals, but my space isn’t large enough to comfortably or safely host additional pets. Because of that, I offer care exclusively in your home, where your pet feels most secure and where their routine stays consistent. When I’m caring for your pet, I follow your house rules and make sure your pet’s environment stays familiar and stress free. My goal is to respect your home, maintain your pet’s routine, and give them attentive, loving care while you’re away.

“Olivia is great! She was punctual, easy to communicate with, and comfortable walking my 55 pound (one year old) dog, who tends to pull on the leash. I would happily hire her again!”

Katie B.

“Sarah did a wonderful job.. she clearly loves dogs and is very good with dogs. My pup was so comfortable with her. Definitely recommend Sarah.”

Ann G.

“Sanela is a phenomenal dog walker! She is attentive, personable, communicative, and timely. She takes my dog Tully on nice long walks and he loves her. I’m so happy we found her, and I highly recommend!”

Caroline H.

“Sarah was great! Very responsive and thorough. Would definitely book her services again 😊”

Charlotte M.

“Noila was very prompt and walked Miles without any issues. She had a last minute adjustment close to the time and had to modify the booking, but she was very apologetic and professional about it. We would definitely use Noila’s services again.”

Maple G.

“Sophia was such a pleasure to work with. Sophia came on time and collected Dakota and Bogomila on a walk replete with photos and helpful commentary. I look forward to working with Sophia in the future”

David C.

“Jacqueline is awesome! So patient with my crazy, energetic pup. Piper absolutely loves when Jacqueline comes for her walks and waits for her to return when she leaves!”

Chrystine L.

About: I've always loved taking care of dogs! I had my first when I was 9, a beagle. Throughout the years I've done various dog-walking and dog/cat sitting for friends and family, and now I miss seeing all the dogs as I live away from them and they have passed :'( On multiple occasions, I took care of two loving but rambunctious pit bulls for weekends and extended periods of time while my friend was away. Gave them medicines, lots of attention, and invigorating walks. I took care of the house while they were away and sometimes stayed overnight. I have experience with dogs that need to be on a tight leash in certain scenarios, and experience allowing them to just have fun in safe spaces. With well-behaved dogs, I've gone on runs in the forest and been able to have them off-leash. I love having a buddy! I care a lot about maintaining the boundaries and rules around how you have trained your pet and keeping their routines. I manage an office nearby Monday thru Thursday, flexible Fridays. The morning walks are reliable and I can message you specifics and sort your dog’s and my schedule around it :) Most days, the afternoon walk can be configured into the schedule. We have a larger yard and no pets living in the house. My sisters nearby both have friendly dogs if yours would like some pals. Some days are busier or have a tighter walk schedule for me, but usually just 2 weekdays, which is why this works for me! I love taking dogs to different adventures like the Fells or games in my backyard, or just hanging out and cuddling :)

About: I’ve had dogs and cats my entire life, so I’m very comfortable caring for pets of all ages and personalities. I’m patient, dependable, and attentive to each pet’s individual needs, whether that means going on walks, playing, feeding, administering basic care, or simply providing companionship. I understand how important it is for pets to feel safe and loved while their owners are away, and I’ll treat every pet as if they were my own. My lifelong experience has taught me how to recognize changes in behavior and ensure pets stay happy, healthy, and comfortable. Pet care is a large part of my daily life. In my home we have two cats (Max and Binx) and one extra large Labrador (Trixie). I change litter, feed my pets, and take Trixie out to the bathroom and for walks. Although I haven’t professionally cared for clients’ pets yet, I’ve had dogs and cats my entire life and understand the responsibility that comes with caring for them. I always make sure pets have fresh food and water, plenty of exercise, attention, and a safe environment. I’ll carefully follow any instructions provided by owners to keep their pets comfortable and maintain their normal routine. I treat every animal with patience, kindness, and the same level of care I give my own pets.

About: I’ve grown up caring for a wide range of animals and have extensive experience walking both small and large dogs; rain or shine. I tailor each walk to your dog’s needs, whether that means a relaxed pace or a more active outing while equally maintaining any training routines you’ve established. I’m also experienced with senior dogs and can provide gentle walks, rest breaks, or additional support as needed. Your dog’s safety, comfort, and happiness are always my top priority! I am a freshman university student returning back home to Massachusetts for the summer, currently working part-time. I am free most days for regular walking, but will be occupied Monday and Wednesday evenings for extracurricular classes. I am generally flexible and will manage to work around your schedule! I provide reliable and respectful in-home visits, ensuring your dog is cautiously handled and returned as instructed. I carefully follow your instructions, including access, routines, and any specific care needs, so your pet’s day stays consistent. You can trust that I treat your home and your dog with the utmost professionalism at all times.

“Rebecca was wonderful! She took the time to come meet Mr. Lahey before care and he immediately could tell she was a true animal lover! Did a wonderful job caring for him, as well, and very good at communicating! Highly recommend Rebecca for all your pet needs haha”

Jake O.

“Angela has been a lifesaver. She was quick to respond when we needed a last minute, recurring walker and worked around our hectic schedule for a meet and greet. Our two labs absolutely love her and look forward to their morning walks. She’s communicative and considerate and I also look forward to seeing her in the mornings as she has a great personality! She’s a pleasure to work with and we are lucky to have found her. Highly recommend!”

Catherine S.

“Extremely dependable and arrives exactly when promised - she was so prepared that she even brought towels to dry off the dogs when it was very wet outside! Thanks again!”

Jonathan L.