Dog walking in Pleasantville

Pleasantville Town Center

Every pups’ favfurite part of Pleasantville is the Pleasantville Dog Park. Nestled in the heart of the Village Center on Castleton Street, it’s the one place in town where dogs of all size can roam free off-leash and socialize. The park has water fountains and waste bags for pups, too. If you’re feeling more like whining and dining, check out the Ironhorse Grill. When the weather is nice, it’s a grrreat place to grab a meal or a cocktail. Their specialty is seafood, but they also have delicious salads and desserts (for humans only). Just ask the host for a dog friendly outdoor table.

Mount Pleasant

Mount Pleasant is a flufftastic area to check out if your dog likes long walks and lots of smells thanks to its two large parks. Graham Hills Park is a pawsome place to spend time with your four-legged friend. You’ll need to keep your dog leashed, but there is plenty of space to explore, over 430 acres. The park even has doggy waste stations! Aside from the open fields, the Graham Hills Park Trail offers a 3.6 mile paved path. The trail meanders mostly through the woods, meaning there’s plenty of shade. The Rockfeller State Park Preserve is also a real treat. It features views that will leave you panting, including the lovely 22-acre Swan Lake. To really take it all in, you can walk one of the three carriage roads that meander through the rolling hills and lush greenery. You could also try the 13 Bridges Loop Trail, a 1.9 mile hike that leads you over 13 bridges along the Gory Brook.

East Briarcliff Manor

The town of Briarcliff Manor is woodsy and woofderful, and it’s right next to Pleasantville. Grab the trailhead to Hardscrabble Wilderness Trail on Dogwood Lane, and then venture out for a tail waggin’ good time. The 3.5 mile trail features a pond where your pup can do a little doggy paddling, rocks to climb, and flat terrain for walking and jogging-- all on-leash. The path itself is mostly made up of dirt, gravel, and crushed leaves, so unless you trust your dog to mark a path, you’ll want to keep an eye on the trail. Waste bags, water, and tick treatments are also all good ideas. Briarcliff has some furrific food, too. If you’re looking for the best pupperoni pizza in town, look no further than North State Pizza. Dogs and their humans are welcome to sit at any of the tables outside while they chow down.

Sleepy Hollow Village Center

While Sleepy Hollow is probably best known for its headless horseman, this town's Village Center neighborhood is also a splendi-fur-ous place to stretch your legs. Kingsland Point Park is one of the most pawmazing places to spend a day. First of all, within Kinglsand Park is the Sleepy Hollow Dog Run, an off-leash dog area where dogs can run, bark, and dig to their delight. Perk up your ears, though, because you’ll want to remember this: to enjoy the park, you MUST pay a small fee for an annual permit. The 18-acre park is also full of fields and beautiful views of the Hudson River that can be enjoyed by leashed dogs and their humans. There’s a playground for kids, and you won’t want to miss seeing the historic Tarrytown Lighthouse. When you’re feeling like it’s time to fill your bowl, you and your pup can enjoy Greek food at any of Santorini Greek Restaurant’s outdoor tables. Nothing better for the humans than ending the day with a bark-lava.

Chappaqua Town Center

Pleasantville’s neighboring towns are just a pleasant for pups. The Town Center area of nearby Chappaqua is quite fur-riendly. The best part of town is undoubtedly the Gednery Park Off-Leash Dog Area, located in Gedney Park. With the exception of the playground area, well-behaved dogs are allowed to roam free throughout the 126-acre park. There are trails, education stations, and wide open fields. We recommend trying the 2.1-mile Red Trail. You’ll find a trailhead right near the ballpark barking lot. If you don’t mind an on-leash experience, you’ll also find beautiful wooded trails at the Pruyn Sanctuary. This 92-acre park has 1.9 miles of walking trails that go through swamps and streams, and include educational plaques. When you’re starting to feel like you might gnaw on a bone, try Le Jardin du Roi instead. This French bistro and barbeque has a great menu for breakfast, lunch, and dinner. They’ll also provide your pup with water, and if you ask nicely, they’ll serve him up some chicken too!