Dog walking in Windham

Book on demand and scheduled walks with local dog walkers

How it works

Flexible scheduling

Select the date and time that best suit your needs. Want a walk ASAP? We’ve got you covered.

Customized for your pup

Choose between a 20-minute, 30-minute, or 60-minute stroll for your dog.

Follow along

Track your walk with our live GPS tracker, then view your detailed report card after the walk.

What is Wag!?

Wag! is the nation's fastest-growing network of pre-screened and insured pet sitters and dog walkers. In less than 15 minutes you can book a nearby dog sitter, daycare provider, or dog walker, who'll take complete care of your loved one - at their place or yours.

Book walkers near you

Stacey CWindham, ME 04062

5.0

(760)

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“Extreme Animal Lover! Hug your furbaby!”

Hi! I am a huge dog lover (currently have 2 Goldens) who walks my dogs every day (unless it's raining hard or there's a severe wind chill). I love all dogs. I do not walk dogs on prong collars. I prefer a harness or gentle leader. I am a school teacher and have lived in my home for about 15 years. I've hired dog walkers in the past myself (when my dogs were puppies and needed to get out more on work days). I am the person who, when not with my dogs, stops to meet other dogs along my way.

Background Checked

High Demand

Top Pet Caregiver

Specialties

Dog first aid and/or CPR, Oral medicine administration, Senior dog care, Special needs dog care, High energy dogs, Dogs who pull, Puppy care, Fast walker

Brenda HWindham, ME 04062

5.0

(88)

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After many years of working in customer service, I decided to pursue my love of animals further. Aside from spending time with my own pets, I also volunteer at the AWS shelter in Kennebunk. I assist in puppy training, obedience and walking shelter dogs. My dog and I have taken courses in obedience, tricks, agility, Wag-It, conditioning and even circus dog. I am reliable, responsible and compassionate. Your dog and I will have lots of fun!

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Top Pet Caregiver

Specialties

Dog first aid and/or CPR, Can run with dogs, Senior dog care, Special needs dog care, High energy dogs, Training experience, Dogs who pull, Puppy care, Fast walker

Maggie JWindham, ME 04062

5.0

(48)

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“Outdoor enthusiast and friend of dogs!”

I love being active and spending time with animals! While growing up, I tried my hardest to convince my parents to adopt dogs, but had to settle for hamsters, guinea pigs, and rabbits. I have always had an affinity for animals, but have felt especially connected to dogs, which lead me to begin dog walking for friends when I was only five years old. Since then, I have spent countless hours walking and taking care of dogs - I hope I have the opportunity to spend time with your pup soon, too!

Background Checked

High Demand

Top Pet Caregiver

Specialties

Can run with dogs, Training experience

Rose MWindham, ME 04062

4.9

(562)

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“entrust your pet to me when you are busy or away”

My name is Rose. I am a conscientious, trustworthy pet lover who have grown up with dogs as part of my family. I have a 7-year old golden named Daisy and an energetic 10-year old Maltese mix named Gordie. We love to go for walks and explore new places. I also have 2 rescue cats, 13-year old Izzy and 3-year old Fred. For the past three years, I have been an active volunteer at the ARLGP. I look forward to working with you and your beloved pet or pets.

Background Checked

High Demand

Top Pet Caregiver

Specialties

Dog first aid and/or CPR, Can run with dogs, Oral medicine administration, Injected medicine administration, Senior dog care, High energy dogs, Training experience, Dogs who pull

Matthew QWindham, ME 04062

4.9

(428)

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Hello, my name is Matt! I am an avid dog lover and would like to spend some quality time with your doggo. Born and raised in Portland, I enjoy the city and everything that comes with it. Sports are a big part of my life; been involved with them since day one. Being active is also very important to me: I love going on bike rides, working out, runs, etc! But most importantly, I'm here to build a connection with your dog and hope to make a friend for life!!!! If you have any questions, just ask :)

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High Demand

Top Pet Caregiver

Dianne FWindham, ME 04062

4.9

(223)

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“Puppy~Senior Care & Everything in Between”

I grew up with cats, dogs, rabbits, guinea pigs, & a box turtle. I worked in a Grooming Salon, a Veterinary Hospital, & a local Super Pet store. I have trained in Obedience, Agility, Trick Dog, & Wag-It. Currently I own 2 Black Labs that are in Agility Training, Trick Dog Titles , & Wag-It Games. My 4yo Lab has recently completed the Therapy Dog Test...I have walked 2-3dogs @ a time, plenty of practice walking dogs &... keeping their safety my #1 priority. I treat every Pet as if it's my own

Background Checked

High Demand

Top Pet Caregiver

Specialties

Dog first aid and/or CPR, Can run with dogs, Oral medicine administration, Injected medicine administration, Senior dog care, Special needs dog care, High energy dogs, Training experience, Puppy care, Fast walker

Mike PWindham, ME 04062

4.9

(89)

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“Live fast. Pet dogs.”

Hi everyone, My name is Mike. I’m a graduate student at USM hoping to do a little more while I work toward my degree. Ive had dogs since I was a little kid and currently my own puppy so I’m sure I’ll love hanging out with your fur buddy. I’m an early riser and I enjoy the cold so I’ll be happy to keep your fren walked even in Maine winters. Thanks for reading. Hope to hear from you soon.

Background Checked

Top Pet Caregiver

Specialties

Can run with dogs, High energy dogs, Dogs who pull, Fast walker

Melissa GWindham, ME 04062

4.9

(91)

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Hello! I've loved dogs ever since I was a little girl but because of my family's living situation i have never been able to own one myself. Because of this I am filled with love and knowledge for an animal that has no outlet. I do own 3 cats and a bunch of fish wich receive much love and spoilage. Hopefully with the profits I make from walking I will be able to continue to spoil them!

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High Demand

Sarah WWindham, ME 04062

4.9

(68)

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My name is Sarah and I have been a dog owner and a dog lover my entire life. I have been fostering rescued dogs for several years now and helping them find homes, so I am very experienced! I have been around all sizes, breeds, personalities, and ages of dogs so I know how best to interact with different kinds of dogs. I understand the magnitude of responsibility that comes with walking someone else's dog; I can ensure that I am capable of being a loving and trustworthy dog walker for your pet!

Background Checked

High Demand

Top Pet Caregiver

Specialties

Dogs who pull, Puppy care, Fast walker

Jack KWindham, ME 04062

4.8

(82)

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My name is Jack, I’m 21 years old and I go to college in Hoboken. I study music, and I’m originally from small-town Maine. I’ve grown up with pets my entire life and back home I currently have a golden retriever who is five named Enzo. I’ve always been around dogs and I’m very comfortable with them and controlling them in public around other animals.

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Dog Walking in Windham

Dog-friendly Windham is in southern Maine’s Cumberland County, near Portland. It lies along the Presumpscot River and Sebago Lake, and both bodies of water provide outdoor adventure opportunities for dog lovers and their pooches. Windham also contains a number of parks that offer activities year-round for outdoor enthusiasts.

Donnabeth Lippman Park is 123 wooded acres where dogs are welcome to join their humans for birding and wildlife-watching, fishing on the 10-acre pond, and hiking. Lippman Park features a 1.5-mile multi-loop hiking trail that is groomed in the winter to accommodate snowshoeing and cross-country skiing. The largest loop circles Chaffin Pond, which is a perfect fishing spot. The trailhead is located at the park entrance off Route 302, and you will find an information kiosk there, as well as a picnic area. The terrain makes for mostly flat and easy walking. There’s plenty of parking, too. Pawsome!

After your hike at Lippman Park, head over to the Bomb Diggity Bakery and Café for breakfast or lunch. Fido can be tied to one of the outdoor tables while you go inside to order up some of their baked goods or a sandwich. Locals recommend the pastrami hash! They also offer several gluten-free and vegan menu items. Bone appetit!

So bring your pup for adventure in Windham!

Best Dog Neighborhoods in Windham

Frye Island/ St Joseph's College of Maine

48
Dog Parks
-6 parks

Population Density
450 per sq. mi.

Frye Island/ St Joseph's College of Maine

48

A short way from Windham Center in the town of Standish lies Sebago Lake, the deepest and second largest lake in Maine. This lake is so large, it is bordered by 6 communities including Windham, and it has a large island in the center that fills up with residents in the summer. It provides most of the drinking water for the city of Portland, but it is also the center of many outdoor activities loved by both human and pup. Sebago Lake State Park’s 1400 dog-friendly acres surround the lake and feature woodlands, sandy beaches, ponds, bogs and the Presumpscot River. Many marked trails crisscross the park, which is open year-round and offers opportunities for snowshoeing and cross-country skiing in the winter. Motorized, sail and paddle/oar boating on the lake, swimming, camping and fishing round out the list. Pooches are welcome on the beaches between October 1 and March 31, and in the rest of the park on leash year-round. Certain parts of the campground areas are designated for campers with leashed pets. One of southern Maine’s true gems, a visit to Sebago Lake and the Park is a must-do! 

Cumberland

36
Population Density
312 per sq. mi.

Cumberland

36

The town of Cumberland sits next to Windham and is home to the Town Forest Park, which includes the Town Forest Trail. This is a dog-friendly tract that loops mostly through forest with dirt, grass and crushed gravel trail surfaces. There is one large loop that will bring you near the Public Works and ball field, and another trail that traverses only the areas of forest, mostly flat but with the occasional tree root obstruction. No problem for Fido, but be careful with your own safety. You will also encounter some swampy areas, so you may want to wear boots. A rustic wooden bridge made from small tree limbs lashed together carries the hiker over a small brook, and there are open fields along the way, too. This is a great place to explore, watch for birds and wildlife and just breathe in the fresh woodsy air. Woofderful!

Windham Center

24
Population Density
292 per sq. mi.

Windham Center

24

Windham Center is the commercial and business area of Windham, full of stores, gas stations and restaurants. And because it incorporates most of Highland Lake, there are many waterfront cottages available for rent. If you’re looking for a scrumptious seafood meal, there’s no better place than Bob’s Seafood on Route 302/ Roosevelt Trail. Bob’s serves sandwiches, fish tacos, chowders, dinners and baskets, all made with fresh seafood and accompanied by delicious sides like his homemade cole slaw and fries. There are also burgers and chicken for the “turf” lovers! Enjoy!

South Windham

12
Population Density
303 per sq. mi.

South Windham

12

The dog-friendly Mountain Division Trail meanders through the nearby towns of Standish and Gorham before arriving in South Windham. This easy trail travels along a 5.7-mile paved road in, as well as along the now unused railroad tracks of the old Maine Central Railroad. As it follows the Pleasant River, there are many spots where you and Fido can stop to explore the river and to fish. A trestle bridge provides views up- and downriver, with birds and wildlife in abundance. This neighborhood is also home to the 308-acre Roscoe and Elva Lowell Preserve, with its 5 named hiking trails and 10 cross-overs between loops. This is the largest trail system in Windham, and your furry bestie can join you as you explore the Preserve!

North Windham

0
Population Density
571 per sq. mi.

North Windham

0

The North Windham neighborhood is home to the Claman Sanctuary, an undeveloped tract of land that is well-known for the High Bush Blueberries that grow there in the summer. This land is open to public use, but there is no designated parking area or trails, so you and your fur-pup need to be willing to park by the side of the road and blaze your own path, but the effort will be worth it if you love plentiful, free blueberries!  North Windham is also where you’ll find the pup-friendly Otter Brook Sanctuary, featuring a moderately difficult .8 mile out-and-back trail that passes through tree plantations, woods and wetlands. The two trailheads are both a short walk from River Road, and there is free parking. Woof!