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If you want to embrace the most colorful and eerie of all the four seasons, Sleepy Hollow—home to Washington Irving’s horror novel about Ichabod Crane and the Headless Horsemen—is a good place to go. 30 minutes after departing from Grand Central Station, your trip begins at the Tarrytown Station. From Depot Plaza, a six-block meander down Main Street leads to the dividing line between North and South Broadway, one of the main vessels of its charming, historic downtown.

Walking down Broadway, there are as many antique venues as there are Starbucks in Manhattan. The line between junk store and antique shop can often blur, but in Tarrytown, you are granted both quality and quantity in all of the numerous shops. Filled with rare old objects, Pretty Funny Vintage offers a wide selection of furniture, clothing, and trinkets. Further down Broadway is Whimsies Incognito, which is somewhere between a gift shop and a gallery, stocked with everything from The Indie Rock Coloring Book to kitty greeting cards to local artisan crafted house wares.

Along the way, stop into the cozy and quaint Silver Tips Tea Room for a pot of ginger peach tea and a balsamic turkey wrap. Some patrons may be on luncheon dates, while others nestle into a good book, sipping coffee and nibbling on baked goods. Turn the corner down Main Street, popping into Carol Master Galleries, which offers a more retro spin on the antiquing experience. Across the street, the historic Tarrytown Music Hall, built in 1885, is a historic theater that will be hosting the likes of Neko Case, Sharon Jones and The Dap-Kings, and Mavis Staples in the upcoming months. Next door, Flying Fingers Yarn Shop is a destination for knitters and carries a quality inventory of supplies. As an added bonus for the knitting enthusiasts, Flying Fingers has a free Yarn Bus that picks up at multiple locations in Manhattan on Saturdays and Sundays. Just set up a reservation by emailing them. Grab a cone of homemade Bumpy Road ice cream at old-fashioned parlor-like Main Street Sweets.

You have two options for exploring historic Sleepy Hollow Cemetery from the corner of Main Street and North Broadway in Tarrytown. Travel route #1: You could walk or bike north on N. Broadway 1.3 miles. Travel route #2: You could turn back to the Tarrytown station on the Hudson line, and head outbound one stop to Philipse Manor. The time difference according to the Google Maps estimate is negligible, leaving the choice up to what your legs are ready for.

Opting to walk, one can cross over the bridge featured in the fabled chase sequence of The Legend of Sleep Hollow and enter the portal of yesteryear’s haunted masterpiece. Just off the grand gated entrance of the cemetery is The Old Dutch Church, which was constructed in 1685. The surrounding cemetery is more charming than frightening, offering a combination of head stones and mausoleum’s from a variety of time periods. Dating back as one of the oldest cemeteries in the country, it houses the cadavers of such notable characters as Andrew Carnegie, William Rockefeller, Leona Helmsley, and of course, Washington Irving and many of his extended family members. You could kill an afternoon wandering through this sprawling graveyard, following the points of interest on their complimentary map. If you prefer an in depth tour of the graveyard, historian Jim Logan offers afternoon and evening lantern tours with advance reservation which can be arranged at SleepyHollowCemetery.org.

Both Tarrytown and Sleepy Hollow have a rich line-up of fall and Halloween events filling the month of October. Everything from a Jack-o-lantern blaze, Scarecrow Invasion, to hay rides, a Halloween Parade, and a reading of The Legend of Sleepy Hollow. The full calendar events of all this local can be downloaded at Sleepy Hollow Cemetery’s website above.

How to get there: From Grand Central Station, take the Hudson Line on Metro North to the Tarrytown or Philipse Manor stops. Consult the map below for specific locations.

Map of Featured Locations in Tarrytown and Sleepy Hollow

View Exploring Historic Tarrytown and Sleepy Hollow in a larger map

Sleepy Hollow Cemetery

Visit Washington Irving's grave

Irving Family Plot

Mausaleum

Irving Headstone

Headless Horseman Bridge

Headless Horseman Bridge

On Headless Horseman Bridge

Graveyard in Sleepy Hollow

Amidst the Graves

Ye old grave sites

Carol Master Antiques

Pretty Funny Vintage Typewriters

Pretty Funny Vintage goods

Tarrytown Music Hall

Carol Master interior

Whimsies Incognito

Main Street Sweets

Map It |

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