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A Day in Sleepy Hollow: Crafting Your Perfect Adventure Itinerary

Sleepy Hollow

Located along the pastoral banks of the Hudson River, Sleepy Hollow, is a delightful village steeped in history, mystery, and natural beauty. This enchanting locale has countless attractions to offer, though you can squeeze some into a day or perhaps a weekend of adventure. 

Based on our guide to the top attractions in Sleepy Hollow, here’s a curated sample itinerary that will take you to some of Sleepy Hollow's most captivating attractions. 

Start Your Day With A Morning Stroll

Embrace the tranquility of Riverwalk Park with a leisurely morning stroll, the perfect start to your day. As the morning sun gently illuminates the Hudson River, wander along the peaceful pathways adorned with ancient trees, taking in the serene vistas and the calming whispers of nature. Engage in this serene ritual, sharing the enchanting ambiance with fellow early risers, before venturing forth to explore the captivating allure of Sleepy Hollow. 

Washington Irving's Sunnyside

Just a short drive from the hotel is Washington Irving's Sunnyside, the former home of the legendary author of "The Legend of Sleepy Hollow." This much-loved landmark is the perfect place for a morning stroll: you can explore the beautifully preserved estate, admire the lush gardens, and enjoy the picturesque views of the Hudson River that inspired Irving's tales. Tickets are available here

Lyndhurst Mansion

Continue your architectural tour of Sleepy Hollow with a visit to Lyndhurst Mansion, a stunning example of Gothic Revival magnificence. A leisurely 22-minute walk from Sunnyside will get you to Lyndhurst, which also features opulent interiors, impressive gardens, and breathtaking views of the Hudson Valley. 

Lyndhurst is more of a classic estate, however, compared to Sunnyside — it will transport you straight to the British countryside. It also has a claim to fame as the residence of former NYC mayor William Paulding Jr. and railroad magnate Jay Gould.


There are many culinary delights to choose from in Sleepy Hollow, from farm-to-table hotspot Blue Hill at Stone Barns — which has two Michelin stars — to homey Bridge View Tavern. Any of the spots on our guide to the dining scene in Sleepy Hollow will be sure to satisfy your taste buds after a morning of exploration. Read more here

Sleepy Hollow Cemetery

After a morning admiring the architectural highlights of the town, it’s time to delve into the mystique of the place. A visit to Sleepy Hollow wouldn't be complete without a trip to Sleepy Hollow Cemetery, a resting place as historic as it is hauntingly beautiful. 

Here, you’ll find the final resting places of notable figures like Washington Irving, Andrew Carnegie, and Elizabeth Arden. The stunning yet peaceful ambience and its gothic architecture make the cemetery an ideal spot for a leisurely stroll.

Old Dutch Church

A short nine-minute walk from the cemetery is the historic Old Dutch Church, a spiritual location that will let you journey back in time. This iconic place of worship has been around since 1685, and it is an important feature of “The Legend of Sleepy Hollow,” as the Headless Horseman’s haunting ground. It’s a must-see for visitors to Sleepy Hollow, especially those fascinated by the mythology of the town. Keep in mind that the grounds close at 4:30pm. 


All that walking around is sure to make you hungry, so indulge in a delectable dinner in downtown Sleepy Hollow. Whether it’s Mint Premium Foods or the Bridge View Tavern, there are restaurants all over the town and in the greater Hudson Valley that will serve as the perfect wrap-up to a busy day. 


After dinner, return to luxury at the Sleepy Hollow Hotel, where you can rest, sit outside, take a dip in the pool, or get a workout in. Our tranquil setting and impeccable service provide the ideal backdrop for unwinding and reflecting on your day in Sleepy Hollow. Remember to check the Sleepy Hollow Hotel website for the pool hours.

Enjoy a day of adventure and discovery in the charming town of Sleepy Hollow. Book your stay now!