Home Blog Uncovering the Past: Exploring Sleepy Hollow's Historic Sites

Uncovering the Past: Exploring Sleepy Hollow's Historic Sites

Sleepy Hollow Historic Sites

While Sleepy Hollow may have a quiet, small-town feel, it is also steeped in American history. A perfect way to appreciate this history is by touring some of the most well-preserved architectural wonders of Sleepy Hollow. Many are less than a ten-minute drive away when staying at the Sleepy Hollow Hotel. Explore these beautifully preserved architectural wonders of Sleepy Hollow. 

Philipsburg Manor

Located in the heart of Sleepy Hollow and just over two miles from the Sleepy Hollow Hotel, the Phillisburg Manor is one of the best architectural wonders to visit. The Phillipse family once owned this trading complex and mill. While visiting, you will learn about the family that owned the complex. Tour the white-washed stone building and additional wooden structures to experience life for the enslaved people who operated the dairy and gristmill. 

Kykuit, the Rockefeller Estate

For four generations, the Rockefeller family called Kykuit home. This historic mansion, built in 1913 and with 40 rooms, has a Classical Revival style of architecture. The estate was opened to the public in 1991. 

To visit Kykuit, you must join a tour that starts at the Philipsburg Manor. A shuttle bus will take you to the manor for your tour and then return you afterward. Visitors can attend a guided walking tour through the home and grounds. Three tours are available: a 90-minute highlight tour, a just-over-two-hour classic tour, and a three-hour grand tour. 


The Sunnyside cottage is the much-loved home of Washington Irving, author of The Legend of Sleepy Hollow. Irving bought the house and began customizing it as the perfect picturesque cottage. He expanded on the home while adding architectural elements that appealed to him. This included Gothic windows, a Spanish tower, Dutch stepped gables, and Tudor-style clustered chimneys. During your home tour, you will see many of the original furnishings. Sunnyside is just over one mile and less than five minutes from the Sleepy Hollow Hotel. 

The Tarrytown Lighthouse

This sparkplug-style lighthouse once stood a half mile off-shore. Today, the shoreline is within a few feet of the lighthouse due to years of landfill created by the now-demolished General Motors factory. Built in 1883, this cast iron lighthouse stands five stories tall. Over the 78 years of operation, 12 lightkeepers and their families called the lighthouse home. When staying at the Sleepy Hollow Hotel, you are just over two miles or less than a 10-minute drive from the lighthouse. Visitors can take a guided tour of the lighthouse during the summer months. 

Union Church of Pocantico Hills

Drive about three miles from the Sleepy Hollow Hotel and outside of downtown Sleepy Hollow to find the Union Church of Pocantico Hills. This quaint church is home to some of the most elaborate and beautiful stained glass work in Hudson Valley. The Rockefeller family commissioned the stained glass pieces from European glass masters Henri Matisse and Marc Chagall. When the sun shines, the inside of the church comes to life in an explosion of color. This is an active church. While you can visit and take a tour, you must make arrangements in advance and do so around the congregation’s activities. 

Discover Sleepy Hollow’s Architectural Wonders 

Many of these architectural wonders in Sleepy Hollow have operating hours and tour schedules that change throughout the year. Book your tours and visitings ahead of time to ensure you get to see everything. From the old mill at Philipsburg Manor to the quaint comfort of Sunnyside and the extreme wealth and elegance of Kyuit, there is plenty to see for those looking to enrich their visit to Sleepy Hollow. 

Book your stay at the Sleep Hollow Hotel and be at the center of Sleep Hollow’s architectural wonders.