How it works
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.
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
Hi! My name’s Maddie. I grew up with dogs and absolutely love them. I have volunteered at animal shelters for over 10 years. I’ve undergone all the training to look after your furry friends. What sets me apart is my caring attitude. I go above and beyond for my loved ones and show the same curtesy to my four legged friends, too. I promise you, there is no one better to look after your four legged furry friend.
Hi, I'm Jessica! I've had pets my entire life (dogs & cats!) I believe that compassion is the best way to approach our four legged friends and I have worked with various breeds through adopting rescue dogs, volunteering at animal shelters such as the ASPCA and helping out friends and family members with their pets. I live a very active lifestyle and one of my favorite activities is hiking with my dog DJ.
Top Pet Caregiver
Can run with dogs, Oral medicine administration, Senior dog care, High energy dogs, Fast walker, Dogs who pull, Puppy care, Socialization training, Puppy training
Dog Walking in Winchester
If you and your dog love hiking through beautiful forests and up mountains together, Winchester is the perfect place for you. This New Hampshire town has one dog-friendly park, and it’s just a short drive from many other great parks that welcome dogs on- and off-leash. While there are no veterinary clinics in Winchester, there are many good options in nearby Keene, Jaffrey, and North Swanzey.
If you’re looking for a pawesome place to trek with your dog, check out Mount Grace State Forest. This stunning forest is seven miles from Winchester, and it welcomes dogs on-leash. If you want to go on a long hike with your pup, try the 3.9-mile Mount Grace Long Loop, which takes you through a forest and provides amazing views of the nearby mountains. Or, you could try the 2.6-mile Mount Grace trail, which takes you to Mount Grace’s summit. Bring water and doggy bags, and enjoy exploring this peaceful state forest!
Canalside Rail Trail is another great place to take your pup for an on-leash hike. This trail begins in Turner Falls, which is 16 miles from Winchester. From there, the trail goes 3.6 miles south to Deerfield. As you go along the trail, you’ll pass the beautiful Connecticut River, and you’ll also walk over a historic bridge. You and your pup will always have a fun time here and at the many other dog-friendly attractions in and around Winchester!
Best Dog Neighborhoods in Winchester
Pisgah State Park
Pisgah State Park
If you’re searching for a picturesque place to hike with your pup in Winchester, Pisgah State Park is perfect for you. This 13,300-acre park welcomes dogs on-leash, and it has tons of fun trails for you and your dog to explore. If you want to go on a short trek past numerous beautiful ponds, check out the North Ponds Trail or the Lily Pond Trail. Or, if you’d like to go on a longer hike along some of the park’s most scenic ridgelines, try the Pisgah Ridge Trail. Bring doggy bags and water for you and your pup, and enjoy exploring this stunning park.
If you’re looking for a furrific off-leash area for your dog, head to this Orange neighborhood and check out North Quabbin Dog Park. This dog park is located 17miles from Winchester, and it’s separated into three sections: one for large dogs, one for small dogs, and one that’s filled with agility and training equipment. The large and small dog sections both feature big fields for pups to run and play in, and the agility equipment section offers hurdles, ramps, tunnels, and more. There’s no running water in the park, so it’s a good idea to bring some with you. Your pup will love playing in this park!
Located 12 miles from Winchester, Emerald is a mostly commercial area with lots of fun activities to offer pups. If you want to take your dog for an on-leash walk, check out Ashuelot River Park. This 157-acre park is home to the lovely Jonathan Daniels Trail. This trail takes you through the woods, past wetlands, and along the Ashuelot River. Bring some water and doggy bags with you, and enjoy strolling through this park. If your dog is a good boy or girl at the park, treat them to a snack at One Stop Country Pet Supply. This pet shop sells a wide variety of natural pet treats and toys your pup is sure to love!
River Town/South Mountain
River Town/South Mountain
If you’re looking for another pawsitively great place to hike with your dog, try the Northfield Mountain Recreation and Environment Center. This recreation area is located 13.5 miles from Winchester, and it offers 26 miles of trails to explore with your pup. These trails will take you through a forest and past wide-open fields. Water fountains are available if your pup gets thirsty — just be sure to bring their bowl. If you want to go on a scenic picnic after your hike, head down the road to the Riverview Picnic Area. This picnic area is located right on the Connecticut River, and it has tons of tables to choose from.
Prospect is home to another fun off-leash area for your pup, Paws Park. Located 22.5 miles from Winchester, this park has separate fenced areas for large and small dogs to run and play in. It also offers lots of agility equipment for your pup, including hurdles and ramps to climb. If your dog gets thirsty while they’re playing, a doggy water fountain is available. If you’re hungry after the park, head to Greenfield Coffee. This local café welcomes dogs at their outdoor tables, and they serve a wide variety of sandwiches, freshly-baked pastries, and full-leaf teas.