Leaf Peeping in Tarrytown and Sleepy Hollow

Exploring the historic sites along the Hudson River

By Isabelle Kellogg Created: October 10, 2012 Last Updated: October 17, 2012
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The Hilltop Hanover Farm in New York's Westchester County. (Ted Bohlk)

The Hilltop Hanover Farm in New York's Westchester County. (Ted Bohlk)

When a trip to Central Park seems too routine for enjoying the prime fall foliage season, there are several convenient and rewarding ways to approach a leaf peeping trip to the Hudson Valley. Less than an hour outside the city by car or by Metro-North Railroad, the Hudson Valley has a network of historic sites, from castles to mansions, which are best experienced starting off in Westchester County’s Tarrytown. 

If a more leisurely weekend is possible—because there really is that much to do—then plan ahead and include an overnight stay. Either way, there are spectacular views, heritage sites, harvest festivals, and family-friendly events like the Jack O’ Lantern Blaze and Sleepy Hollow Midnight Cemetery Tour, which makes for a memorable getaway destination. 

Key destinations that afford panoramic views of the Hudson Valley’s rolling hills and foliage are all within a short distance of each other and include: Tarrytown and Sunnyside; Lyndhurst, the Gothic Revival mansion; Stone Barns Center, a working farm with myriad ongoing programs and a world class restaurant; and Union Church of Pocantico Hills with stained glass windows by famous artists Henri Matisse and Marc Chagall, all commissioned by the Rockefeller family. If time permits, there is also Van Cortland Manor, Philipsburg Manor, Kykuit, the Rockefeller Estate, Caramoor Center for the Performing Arts and the Katonah Museum of the Arts. 

Founded in the early 1600s by the Dutch, Tarrytown grew to be a major stagecoach stop on the Boston Post Road run. The town even boasts its own historic music hall where today’s major talent performs. If you’re still thinking of that grade school trip to Tarrytown to visit author Washington Irving’s Sunnyside (he wrote “The Legend of Sleepy Hollow” and “Rip Van Winkle”), then you’ll be surprised to see how much has changed—for the better. Daytrippers, visitors, both families and adults, will enjoy more sophisticated restaurants and places to shop. 

Picturesque Sunnyside, Tarrytown, is where author Washington Irving, resided when he returned to America in 1835 after living abroad. The stone cottage is very much the same as it was in his day. Sitting on 10 acres very close to the river’s edge, the house exemplifies the Romantic Movement in America with some quirky design elements like Dutch gables, small windows, a tiny staircase, and a “snuggery,” (what a library was called back then), and wisteria and ivy growing on the facades. 

Irving left most of the landscape in its natural state, but added winding paths for the river vistas as well as carefully placed trees and shrubs for decorative purposes. Call ahead for a tour by the ebullient site manager Michael Lord, who has all the inside scoop on the author and his many famous visitors and neighbors. Sunnyside also boasts a number of well-orchestrated events throughout the fall season, making the most of his character, the Headless Horseman.

In the 19th century, the Hudson River Valley was a hotbed for Romanticism in both literature and painting. Lyndhurst, the imposing yet architecturally restrained mansion situated on the bluffs overlooking Hudson River in Tarrytown, has 67 acres of park-like grounds, typifying 19th century landscape design with sweeping lawns, shrubs, and specimen trees, which are open to the public free every day. This is an ideal spot for enjoying panoramic vantage points. House tours, during the day as well as at dusk reveal a residence rich in decorative arts. 

The Stone Barn Center in New York's Westchester County. (Isabelle Kellogg)

The Stone Barn Center in New York's Westchester County. (Isabelle Kellogg)

As a member of the National Trust for Historic Preservation, there are knowledgeable staffers on the grounds. The mansion was built by Alexander Jackson Davis in 1838 for former New York City Mayor William Paulding. It was later sold to railroad tycoon Jay Gould in 1880. 

What makes Lyndhurst such a stunning example of Gothic Revival design are fanciful turrets and asymmetrical outlines, which were different than most homes constructed in the post-colonial era. A dramatic, covered curving entrance drive reveals surprise views of the river and valley, and the estate’s rooftop has an angular repetition and pattern that is Gothic in style. Whether or not you choose to visit the interior of the mansion, a stroll through the grounds is well worth it. 

Stone Barns Center is an incredible, 80-acre working farm and education center geared to increasing awareness of farm-to-table ingredients and the health benefits of sustainable food. Established by David Rockefeller as a memorial to his wife Peggy, the grounds beg to be explored with their pastures, chicken coops, livestock, pigs, gardens, sweeping vistas, and trails that lie adjacent to Rockefeller State Park Preserve. Lectures and cooking classes feature artisan cooks. The Farm Store is well stocked with books, interesting gift items, and seeds for do-it-yourself gardeners. The café serves delicious snacks and sandwiches, but its on-site restaurant is booked months in advance. Back in Manhattan, you can experience the flavors and ingredients at Blue Hill if you can’t get in to Blue Hill at Stone Barns. 

Now it should be apparent that the Hudson River Valley is Rockefeller Country and the family continues today to provide funds for so many of the sites in the area. The Union Church of Pocantico Hills, in the town of Sleepy Hollow, is an active church, especially on Sundays, and pre-planning is advisable in order to see the famous stained glass windows—10 by Marc Chagall, and one by Henri Matisse. 

The neo-Gothic style sanctuary features a timber roof and fieldstone and was constructed in 1921 for John D. Rockefeller, Jr. When he died in 1960, his family asked Marc Chagall to design a stained glass window. In 1948, Henri Matisse installed his last work of art, a rose window, commissioned by the family in honor of Nelson Rockefeller. Mrs. Rockefeller was one of the founders of the Museum of Modern Art in Manhattan. Another salient feature of this church is the pipe organ, which is based upon the organs of fin-de-siècle Paris, built in 2006 by organ builder Sebastian M. Glück.

It’s also possible to enjoy some very good food in the region at several smart restaurants that also offer excellent vantage points for river views and rolling hills. The elegant Blue Hill at Stone Barns Restaurant in Pocantico features refined American cuisine. Red Hat on the River in Irvington is a lively French bistro set alongside the Hudson River. Harth at the Hilton Westchester offers farm-to-table specialties from the region. 

Isabelle Kellogg is a writer and public relations consultant in the luxury sector, with a passion for diamonds, jewelry, watches, and other luxury products, including travel.

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