Sleepy Hollow, New York {Travel Guide}
- Chey Muter
- 4 days ago
- 5 min read
Happy Friday! I said I was going on a spooky, Halloween-themed vacation. Well, I am so excited to share, I went to Sleepy Hollow, New York. My first-time ever going to New York! We stayed for 3 days in Sleepy Hollow, so I saw and did everything I wanted to do. Sleepy Hollow is a very small town, so it was very easy to get through everything I had on my bucket list. I will share everything I did then recommend some other fabulous places to check out as well. Sleepy Hollow is the most perfect trip for fall. I highly recommend you go in October, to experience all of the spooky vibes.
Where I Stayed
I stayed at the Holiday Inn Express & Suites Hawthorne - Elmsford North. This hotel is 7 minutes from Sleepy Hollow. Renovated and newly opened. I could tell everything was new and clean. There is a complimentary Express Start Breakfast buffet, that we ate every day. It was so good and had a variety of options from eggs, omelet's, sausage, muffins, bagels, cereal, etc. There is a pool, free Wi-Fi, on-site parking, pet-friendly accommodation, and spacious rooms with all the essentials.
Other Places To Stay
Sleepy Hollow Hotel- Conveniently close to several historic sites, with a kosher kitchen and rooms overlooking a serene courtyard. There are a fitness center and an indoor pool. About 1 mile from downtown Tarrytown and 2 from Sleepy Hollow. A little on the pricier side, as it is in the heart of Sleepy Hollow.
What To Do
Sleepy Hollow Sign- This is the iconic roadside attraction for the town, which is the real-life setting for the legend of the Headless Horseman.
Philipsburg Manor- Cross the millpond bridge to Philipsburg Manor, a mill and trading complex where an enslaved community lived and labored for generations. Learn about the enslaved individuals who worked on the property in the year 1750, and whose family relationships and personal histories are revealed in primary documents. There is a nice gift shop where you can pick up some Sleepy Hollow souvenirs as well.
Headless Horseman Statue- The Headless Horseman statue is one of the most visited spots in Sleepy Hollow. This 18-foot-tall sculpture of the Headless Horseman chasing Ichabod Crane was created by local artist Linda Perlmutter and built by Milgo/Bufkin Metal Fabrication. Its 11 tons of steel panels were chemically treated to oxidize a rich cinnamon hue.
Headless Horseman Bridge- Unfortunately, the Sleepy Hollow bridge where Ichabod Crane was unseated by a pumpkin is the most popular destination in Sleepy Hollow that doesn’t exist, at least not in the form and location in which it appeared in Washington Irving’s short story "The Legend of Sleepy Hollow." The simple wooden span that crossed the Pocantico River in the late 1700’s has long since rotted away. In fact, Sleepy Hollow village historian Henry Steiner, has documented at least five distinct bridges that carried the Albany Post Road over the stream. Scarcely a trace remains of any except the most recent, the 4-lane concrete and steel U.S. Route 9 (the modern successor to the colonial-era Albany Post Road) bridge constructed by William Rockefeller in 1912. Even that was heavily modified in the 1930's when New York State reconfigured the route of the road.
The Cemetery Headless Horseman Bridge- In “The Legend”, Irving describes the route of the Albany post road on the east side of the Old Dutch Church (now it runs on the west side), placing Ichabod’s collision inside what is today Sleepy Hollow Cemetery. The cemetery’s own bridge, upstream from where the Post Road bridge stood in Washington Irving’s time, is rustic enough for a selfie. It is on cemetery road Sleepy Hollow Avenue about 0.3 mile inside the cemetery’s south gate. Be respectful, the cemetery bridge is used daily by funerals and mourners visiting graves.
Sleepy Hollow Cemetery- Sleepy Hollow Cemetery in Sleepy Hollow, New York, is the final resting place of numerous famous figures, including Washington Irving, whose 1820 short story "The Legend of Sleepy Hollow" is set in the adjacent burying ground of the Old Dutch Church of Sleepy Hollow.
Sleepy Hollow Lighthouse- Tarrytown Lighthouse in Sleepy Hollow was built in 1883 in response to pleas by local steamship companies for assistance in navigating dangerous shoals. It was a critical guide for Hudson River shipping. The Lighthouse is a cast iron “sparkplug” lighthouse, whose superstructure rests on concrete and metal caisson and is the only conical steel structure in Westchester to include living quarters for its keepers, which housed eight keepers and their families when it was active. Once the Tappan Zee Bridge was built, the lighthouse was considered obsolete and taken out of service in 1961. The Tarrytown Lighthouse in Sleepy Hollow is listed on the National Register of Historic Places.
The Great Jack O’Lantern Blaze- Meander through an 18th-century landscape and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns, all designed and hand-carved on site by a team of artisans. Complete with synchronized lighting and an original soundtrack, this immersive, one-of-a-kind event is not to be missed. This awesome event is the whole reason I went to Sleepy Hollow. I will have a dedicated blog post about this coming very soon. Here is a little sneak peak of this one-of-a-kind pumpkin experience.
Twilight Village- As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers and eerie encounters around every corner. Mingle with Legend icons Ichabod Crane and Katrina Van Tassel, wander through a pop-up market with curious goods, oddities, and handmade wares, and grab delicious bites from food trucks while sipping cocktails and mocktails. Throughout the evening, a roving band fills the air with music, fortune tellers offer glimpses into your future, and the Headless Horseman makes a dramatic appearance in a sound-and-light spectacle that recreates his midnight ride. This second event is also why I went to Sleepy Hollow. I will have a dedicated blog post about this event coming very soon as well.
Where To Eat
Horseman Bagels- Bagel shop and ice cream parlor offering a variety of bagel flavors, plus sandwiches and coffee. How can you not go to Horseman Bagels in Sleepy Hollow?
Horsefeathers- Since 1981, Horsefeathers has been a staple in the village of Tarrytown, offering both classic and New American cuisine. Nestled along Route 9, they are not just a place to dine, but a local legend celebrating the rich history and lore of Sleepy Hollow Country. Halloween decorations fill the entire restaurant with new and vintage pieces. You can feel the spookiness in the air. You have to go here for the festive atmosphere, and the food is pretty good too. Just could use a little more seasoning.
Fast Food Options Sleepy Hollow Has- Chick-fil-A, McDonald's, Wendy's & Applebee's.
Where To Shop
Ona- Combination art gallery and gift boutique, Ona offers some of the best ceramics and jewelry designed by local artists in the area. Ona specializes in Fair Trade products from all around the world.
Trilogy Consignment- There are used, vintage and retro items at this consignment shop.
All Together Now- The cutest little toy store I have ever seen. Bought a Jellycat for my sister's birthday while I was there. There is a cute, vintage mechanical horse you can ride in the store as well.
Sleepy Hollow Souvenirs- Looking for vintage Sleepy Hollow Souvenirs?! This is the place to go to. They have T-Shirts, sweatshirts, artwork, stickers, ornaments, etc.
That is my complete Sleepy Hollow Travel Guide. The most amazing place and so many fun, spooky things to do. I highly recommend staying at least 3 days just so you can see and do everything you want to do while also having time to unwind and relax. My Great Jack O'Lantern Blaze & Twilight Village post will be coming very soon.
Xoxo,
Chey
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