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.
Turn the corner down Main Street, popping into Carol Master Antiques 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 which hosts a ghost tour each fall highlighting historic spirits and spooks. 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.
Sleepy Hollow by Eden PicsBoth Tarrytown and Sleepy Hollow have a rich line-up of fall and Halloween events filling the month of October like their Murder and Mayhem Lantern Tour. 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.
Header photo by Ed.
Map of Featured Locations in Tarrytown and Sleepy Hollow
View Exploring Historic Tarrytown and Sleepy Hollow in a larger map
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram