Looking for the perfect day trip from New York City? Sleepy Hollow, NY, is a charming getaway full of history, nature, and adventure—it’s a perfect dog-friendly break from the city!
🐶 Great for dogs of all sizes!
🍂 Best for Fall (Spooky season and peak Fall Foliage)
🗓️ Best for a day trip
I started my trip at Grand Central Station in New York City, where I hopped onto the Metro-North train. The ride was under an hour, and I loved watching the Hudson River roll by through the window. The trains come regularly, but make sure to check the schedule ahead of time so you don’t miss your ride!
Metro North allows all dogs to ride the only requirement is they are on leash or in a bag and they don’t bother other passengers! You can find the Metro North Dog Policy here.
I got off at Tarrytown and explored the charming town on foot. From the station, I made my way up to the Sleepy Hollow Cemetery. Along the way, I passed Philipsburg Manor, a historic site dating back to the 1700s. While only service dogs can go inside, it’s still worth a look from across the pond to appreciate its history.
The cemetery is peaceful and scenic, with a gentle stream guiding our path toward the legendary Headless Horseman Bridge—thankfully, no ghostly riders emerged to give chase! Along the way, be sure to spot the grave of Washington Irving, the famed author of The Legend of Sleepy Hollow.
After all that walking, I strolled back into town via Broadway, stopping for a picture at the famous Sleepy Hollow sign. Then I made our way to Beekman Avenue, the town’s main street lined with cafés, bars, and shops. A tired pup like me needed a break, so we stopped at Sleepy Coffee Too, where I got to rest and warm up while my human enjoyed a hot drink. Many places here welcome dogs, so it’s a great town for furry travelers like me!
Before heading back to the train station, I took a detour to the Hudson River waterfront stopping to appreciate the Sleepy Hollow Lighthouse. The recently developed riverfront area is perfect for a leisurely stroll before catching the train home.
I visited in early November, after the big Halloween rush. The weather was cooler, but the festive decorations were still up, making the town feel extra special. I’ve heard that October is packed with people and events, but many aren’t dog-friendly, so plan accordingly if you visit during that time.
Overall, Sleepy Hollow is a wonderful spot for a dog-friendly day trip, offering history, scenery, and dog-friendly spots to rest your paws. If you’re looking for an easy getaway from the city, I give it two paws up!