Things To Do in Sleepy Hollow You’ll Absolutely Love

The town of Sleepy Hollow, infamous for the Headless Horseman antics, has attracted the masses. When it comes to things to do in Sleepy Hollow, the list is a bit lengthy, just FYI. Thousands of people rush to the quaint village of Tarrytown, and for good reason. From haunted tours to craft fairs, local shops, festive parades, and charming streets, Sleepy Hollow is perfect for friends, families, kids, couples, and even a solo date. As someone who grew up going to Tarrytown every year (my aunt used to live there), I know a thing or two about the things to do in Sleepy Hollow. Check out this ultimate guide and start planning your trip ASAP! 

Things To Do In Sleepy Hollow: But First, A History Lesson

Before European settlement: The area along the Hudson River where Sleepy Hollow now sits was home to the Wappinger people, a Munsee-speaking group. In the 1600s, Dutch farmers and traders established Tarrytown and the surrounding region. The land was fertile and ideal for wheat and livestock, and Dutch Reformed culture heavily shaped local life. 

The Philipse Family: In the late 1600s, the powerful Frederick Philipse I acquired much of the Hudson Valley, creating Philipse Manor, which included what’s now Sleepy Hollow. His manor house, built in 1682, still stands today as a museum. At its height, Philipsburg Manor covered over 52,000 acres stretching from what is now Yonkers to Croton. The Philipse fortune came from trade, including shipping wheat grown on the estate, importing luxury goods, and, significantly, the transatlantic slave trade. The Philipse family enslaved more than 20 African men, women, and children here in the early 1700s, making it one of the largest enslaved populations in the colonial North. These individuals were skilled in carpentry, milling, farming, and domestic work, and their labor was central to the manor’s success. To make matters worse, the Philipse family sided with the British. In 1779, their vast lands were confiscated by the American rebels as punishment for their allegiance to the Crown. The family fled to England, never returning to New York.

American Revolution: The Hudson Valley was a key strategic area during the American Revolution. The capture of British Major John André (1780) happened nearby in Tarrytown, a pivotal moment for Americans. 

Modern Tarrytown: The village was known as North Tarrytown until only a decade ago, in 1996, when residents voted to officially rename it Sleepy Hollow, embracing the famous legend of Sleepy Hollow

Frequently Asked Questions

When it comes to the top things to do in Sleepy Hollow, you’re going to want to plan your trip accordingly. Here are some frequently asked questions you might not even have thought of, but glad you found them here on the blog!

1. What is the best way to get to Sleepy Hollow? It’s only an hour drive from NYC, but trust me, it gets crowded. You’ll want to take the Metro-North to either Tarrytown or Philipse Manor. 
2. How much time do you need to get the full Sleepy Hollow experience? You can fit everything into one day, but if you really want to spread it out, you can over a weekend!
3. Is everything walking distance? Yes, everything is all walkable. Just be prepared and wear good walking shoes so you don’t hate yourself later. 
4. How soon is Sleepy Hollow decked out in Halloween decorations? How is it during and after Halloween? Decorations start the 3rd and 4th weekends of September!

Things To Do In Sleepy Hollow

Best Places to Eat in Sleepy Hollow: Start your day at either Muddy Water, Horseman Bagels, or some local recs (Los Andes Bakery & Coffee Labs). For lunch and some snacks, check out Horsefeathers and Posh Pretzels to satisfy your sweet tooth and make up all the calories you burned walking. 

Shopping Spots in Sleepy Hollow: Most stores open at 11 am so don’t try to get there too early unless you’re trying to see an empty town. Some fun stores I loved checking out were the, Flying Fingers Yarn Shop, Bellas Boutique, Bark and Meow, La Maison Square & Pretty Funny Vintage

Parks to Visit in Sleepy Hollow: From Neperan Park to Patriots Park, these are two tranquil spots perfect for enjoying a light lunch, a little picnic, and perhaps a break before walking all over the town! Patriots Park is closer to Sleepy Hollow Cemetery and Horseman’s Bagels, which, if you’re starting your day, would be the best bet.

Things To Do in Sleepy Hollow: If You Love History

1. Tarrytown Historical Society: Looking to see just how fascinating the history of this town is? The Tarrytown Historical Society has everything from artwork to archaeological objects, manuscripts, maps, clothing, and educational programs to immerse yourself in the research. If you love history, this spot is perfect. https://www.thehistoricalsociety.net/about/
2. Philipsburg Manor: Philipsburg Manor is a historic mill and trading complex with deep-rooted history in Colonial America. In the 1750s, this house enslaved individuals who worked on the property, contributing to the wealth of the Philipse family. Learn about their way of life, the conditions they faced, and how it impacted Colonial America at the site with self-guided tours of the premises. Check it out https://visitsleepyhollow.com/see/philipsburg-manor/  and get your tickets today! https://tickets.hudsonvalley.org/philipsburg-manor-self-guided-2025/9788
3. Old Dutch Church & Cemetery: Where the iconic Washington Irving is buried, this place is a classic you cannot skip. There are tons of events, both spooky and informational, that break down just how important the people buried in the cemetery are and how much they contributed to society. The cemetery spans 90 to 100 acres with picturesque, spooky views you can quite literally get lost in. 
4. Lyndhurst Mansion: Lyndhurst Mansion is a Gothic Revival mansion filled with history and Victorian lore. They have a really cool event called Lyndhurst After Dark. From October 16th to the 26th, experience the Victorian era from a new perspective. Paired with food, drinks, and decor, you won’t know where to look- there’s so much to offer. https://lyndhurst.org/events/lyndhurst-after-dark/

Things To Do in Sleepy Hollow: If You Love Spooky Events

There’s nothing like spending a festive Halloween spooky day/night in Sleepy Hollow. From cemetery tours to craft fairs and farmers’ markets, there is something here for everyone to enjoy. Think of how perfect a Candlelight cemetery tour is following a Headless Horseman Tour in the iconic town of the Headless Horseman. If you love a lil scare or are willing to face your fears, this is one of those events to put you in the festive spirit. 

1. Sleepy Hollow Cemetery Lantern Tour: On Fridays and Saturdays from 7:30 – 9:30 go back in time and learn why the Sleepy Hollow Cemetery is as famous as it is. Learn about the people who shaped the town, uncover insightful history, and marvel at the architecture. It’s an experience you can only have once so why not make it this season? https://visitsleepyhollow.com/series/sleepy-hollow-cemetery-lantern-tour/
2. Headless Horseman Tours: You not only have one, but 13 interactive haunted houses, walking trails, and corn mazes that will certainly test how brave you are. Think you can handle it? Better yet, bring a whole group of friends/family and bet on who will be the most scared! It’s one for the books and a spot to add to the bucket list. https://headlesshorseman.com/?utm_campaign=GMB
3. Fall Crafts at Lyndhurst: From September 12th -14th, get in the festive spirit at the Fall Craft Fair with your favorite artisans and jewelers alike. It’s the best way to decorate your home and even better way to spend a fall festive day. https://visitsleepyhollow.com/series/fall-crafts-at-lyndhurst-2/
4. Murder and Mayhem Walking Tour: If you love a thrill, then a murder walking tour inside a cemetery just might itch your brain the way it ought to be. On Saturdays from around 7-9pm, get unhinged access to the Sleepy Hollow Cemetery. Listen to horror stories and ghost tales of the past that may or may not give you nightmares even after Halloween. Up for the challenge? Check it out and tell all your friends! https://visitsleepyhollow.com/series/murder-and-mayhem-walking-tour/
5. Farmers’ Market: Because there truly is nothing like homemade apple strudels with fresh apples from the farm. From delicious bread to produce, meat, flowers, dairy preserves, wine, and beer, you are going to have a full fridge for weeks to come, so thank me later. Enjoy events for the kiddos and live music along with educational programs. If you have a pupper, bring them along, but only if they are leashed and friendly! Check them out every Saturday through Nov 22 from 8:30am to 1:30pm. https://visitsleepyhollow.com/series/tash-farmers-market/
6. Pumpkin Blaze: Beginning September 12th, see thousands of hand-carved pumpkins cascade the walkways of Sleepy Hollow. It’s a spectacle worth experiencing. Picture lit up pumpkins almost everywhere you walk, and you’ll want to look everywhere, because there are hand-carved pumpkins every which way. Get amazed and bring your kids, it’s the perfect place, they’ll have great memories of it when they’re older. https://pumpkinblaze.org/

Things To Do In Sleepy Hollow: Spooky Parades & Festivals

Looking for more spooky activities? These are a bit more timely, so you’ll want to secure the plans and make it happen. From witches paddling in the Hudson River to classic Halloween parades, if Fall is your favorite season, this shall solidify that tenfold. 

1. Witches Festival 10/13 1-5pm: I promise you’ll never see witches paddling along Sleepy Hollow than at the SUP Witches of Sleepy Hollow Festival on Oct 12th (rain date Oct 19th). From 1-5pm, enjoy various vendors, live music, delicious bites, brews, and witches galore. If you want to paddle, you must fill out a registration form here https://rivertownssupyoga.com/sup-witches-registration
2. Tarrytown Halloween Parade 10/25, 5-6 pm: The 23rd annual Village of Tarrytown Halloween Parade is the perfect place to dress up, get in the spirit, and enjoy the Halloween fun. Register to march with a group or float and get a chance to win prizes. There’s music, dining, performers, haunted costumes, and way more! The village will be very packed, so please take the Metro-North or Westchester County buses instead. The parade starts at Patriots Park and makes its way south along Broadway to Main Street. For more information, check it out here https://www.tarrytownhalloweenparade.com/

There You Have It 

Sleepy Hollow is truly a town you can spend more than one day in. From all the activities, you might even find yourself coming back weekend after weekend. From the historic charm to the aesthetic village, it’s a great weekend getaway, family adventure, and even a date night! Save all these places to the list and start planning out your perfect day in Sleepy Hollow.

Veronica

Hi everyone! My name is Veronica, but you can also call me Vee! I grew up in the iconic city of Brooklyn, NY, the cultural hub of the world, and hence learned about so many different cultures. It was those experiences that inspired me to travel and from then on, I had learned the power of travel. In return, I want to give others that same experience, to help inspire others to unleash their inner travel enthusiast no matter the trip.

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