19 Things to do in Sleepy Hollow, New York

Are you looking for things to do in Sleepy Hollow, New York? Keep reading for my recommendations!

Sleepy Hollow in New York is a great place to visit for a weekend out fo the city. A place that’s always appealed to Halloween fans, Sleepy Hollow is an excellent place to visit during the spooky season. However, though Sleepy Hollow caters superbly to the Halloween crowd, it’s a fantastic place to visit year-round. With festivals, awesome landmarks, and seasonal attractions that travellers will enjoy no matter their age, it’s no surprise that Sleepy Hollow often finds itself inundated with out-of-towners. 

Now, if you’re looking for the low-down on things to do in Sleepy Hollow, New York, then look no further for we’ve sourced some of the coolest things to do in the area so that you don’t have to.

Lyndhurst Mansion in Tarrytown sleepy hollow

Sleepy Hollow Farmers Market

First on my list of things to do in Sleepy Hollow, New York, it’s the Farmer’s Market! If you love a good Farmers Market, then you’re in luck. With weekend farmers’ markets commonplace in Sleepy Hollow, it’s one of the best things to do in the area if you fancy living like a local. Whether you want to pick up fresh meat, bread, flowers, or dairy products, you’ll find the freshest produce here.

There’s often live music featured at these markets, so you can truly make a day of it! The best one in the area is probably Tarrytown’s and Sleepy Hollow’s weekly farmers market, so make sure you stop by. 

sleepy hollow framers market

Have dinner in a castle

If you’re looking for something romantic and impressive to do in Sleepy Hollow… this might tick all the boxes! Equus is a restaurant located inside the Castle Hotel and Spa, and it’s a fancy restaurant with amazing food and even better views. If you’re looking for a date idea in Sleepy Hollow, this is a great option! This is a great option for things to do in Sleepy Hollow, New York.


Phillipsburg Manor

If you want to explore Sleepy Hollow’s historical side, then be sure to swing by the historic Phillipsburg Manor. Once a thriving farming, milling, and trading center, it was owned by a family of Anglo-Dutch merchants. An excellent place to learn about 18th-century colonial life, it’s one of Sleepy Hollow’s most historic spots. One of the top things to do in Sleepy Hollow. New York according to both locals and tourists, this manor just had to make it onto our list of things to do in Sleepy Hollow, New York.

If you happen to be visiting in October, the manor transforms on select evenings. Becoming a haunted attraction during the month, you’ll have the opportunity to experience some top scares and excellent costumes whilst walking through the historic property! A double whammy we’d say.

Philipsburg Manor in Sleepy Hollow

Headless Horseman Monument

Next on my list of things to do in Sleepy Hollow, New York, it’s the Headless Horseman Monument. If you’ve read The Legend of Sleepy Hollow, then you won’t want to miss the Headless Horseman Monument. One of the top things to do in Sleepy Hollow, New York for literature fans, this headstone monument depicts the famous scene in the story where the menacing horseman appears.

This monument is located at Phillipsburg Manor, so it’s a great idea to pay it a visit alongside your trip to the manor itself. Make sure you bring your camera along for this one, as it’s a truly memorable photo spot!

things to see in sleepy hollowthings to see in sleepy hollow

Kykuit

Kykuit is the next suggestion on my list of things to do in Sleepy Hollow, New York. One of America’s most famous private residences, Kykuit: The Rockefeller Estate is one of the best things to do in Sleepy Hollow, New York. Once home to the renowned oil tycoon John D. Rockefeller in the late 1800s, this amazing six-story stone house is a transportive step back in time.

Visitors can take guided tours of the property and hear stories about the Rockefeller family as they make their way round the property!

Kykuit, the Rockefeller Estate. sleepy hollow

The Great Jack O’Lantern Blaze

Next on my list of things to do in Sleepy Hollow, New York, it’s one for the autumn months. During the fall months, The Great Jack O’Lantern Blaze is a must-visit for those passing through Sleepy Hollow. An amazing night-time display of carved pumpkins that take on various themes, it’s truly a sight to behold. If you’re a fan of Halloween, be sure to book early, as tickets always sell out during peak weekends.

With this festival, you will truly feel like you’ve been dropped into Halloween Town (shoutout to the Nightmare Before Christmas fans amongst you!). Though this isn’t technically in Sleepy Hollow (you’ll need to drive around 20 minutes to reach Croton-on-Hudson), we thought it was too good of an opportunity to leave out of our list of things to do in Sleepy Hollow, New York! 

things to do in sleep hollow pumpkin parade

Visit the Armour-Stiner (Octagon) House

Next on my list of things to do in Sleepy Hollow, New York it’s the Armour-Stiner (Octagon) House is one of the most unique and eye-catching houses in the USA. Yes, that’s a big statement, but wait until you see it, we think you’ll agree. The Octagon House was built in the 1860s by Paul J. Armour, a New York City financier, and it’s really something special – it’s one-of-a-kind and it’s a must-see for anyone obsessed with ‘haunted-style’ houses. This is something you won’t want to miss on this list of things to do in Sleepy Hollow, New York.

This looks like one of those houses you’d see in a ghost / horror movie, and it’s a must-see when you’re in the Sleepy Hollow. Watch the video below for a closer look at this amazing building…

buildings in sleepy hollow new york

The Old Croton Aqueduct

Another one of the top things to do in Sleepy Hollow, New York for history buffs is a visit to the Old Croton Aqueduct. Touted as New York’s first water system, it now functions as a 26-mile walking trail that crosses through both Tarrytown and Sleepy Hollow. Offering stunning views and a great glimpse into both villages, it’s a great one for nature lovers too. 


Take a stroll around Tarrytown

Tarrytown is right next door to Sleepy Hollow (literally you can walk from one to the other) and it’s a lovely scenic, historic town that you can stroll around. On a summer’s day, it’s a lovely town to wander through, and dip in and out of local stores.

tarrytown new york

Order up a beer flight

If you love your beer and trying new brews – then taking a beer flight at the Bridge View Tavern is a great idea. A beer flight is basically a chance to try a variety of beer (in small measures) and sample lots of the local beer talent. The beer flight at the Bridge View Tavern is really well known and a popular choice for things to do in Sleepy Hollow!

beer in sleepy hollow

Sleepy Hollow Cemetery

Another spooky thing to do in Sleepy Hollow, New York is taking a trip to the Sleepy Hollow Cemetery. Though we don’t recommend going after dark if you’re easily scared, the Sleepy Hollow Cemetery is an excellent attraction. Tours are offered during the day that focus on Washington Irving and The Legend of Sleepy Hollow. However, if you’re brave, why not hop on one of the tours that operate after dark? With names like “Murder and Mayhem”, proceed with caution! We jest of course…

things to do in Sleepy Hollow - cemetery

Old Dutch Church of Sleepy Hollow

Old Dutch Church of Sleepy Hollow is the amazing stone church and adjoining burial ground that’s featured in Washington Irving’s story. If you like history, then this is a great option for things to do in Sleepy Hollow, New York.

An atmospheric place to get to grips with The Legend of Sleepy Hollow, it’s certainly one of the best things to do in Sleepy Hollow, New York. Though the cemetery is probably the main attraction here, the adjoining church is certainly worth a look!


Lyndhurst Castle

Who doesn’t love a castle? If you’re looking to see where some of your favourite vampire shows were filmed, then make sure you book a guided tour of Lyndhurst Castle. For film and movie buffs this is a must-do for things to do in Sleepy Hollow, New York.

With a spooky exterior that’s got some great gothic flair, it’s one of the best things to do in Sleepy Hollow if you’re looking to indulge your inner architecture nerd. Trust us, this place is stunning. 

The Jay Gould estate Lyndhurst in sleepy hollow

Spend a day on the river

Sleepy Hollow is right on the river (the Hudson river in case you’re wondering!) so it’s a great chances to do some river-based activities such as boating, fishing, paddle-boarding, kayaking, etc.

Getting out on the river (especially during the spring and summer) is a nice break from the more spooky things to do in Sleepy Hollow, and it’s a chance to just enjoy the great outdoors and the beautiful scenery!


Go antique shopping

You’d expect somewhere like Sleepy Hollow, New York to be popular with antiques hunters. So antique hunting is next on my list of things to do in Sleepy Hollow, New York.

There’s something about the history of this place that means antiques stores seem to have popped up in and around the area. There are quite a few to choose from – so if you’re set on doing a bit of antique shopping, then Sleepy Hollow is a pretty perfect place to do it. You never know what you might find!

Here are some of my top picks for antique shopping in Sleepy Hollow:

best things to do in sleepy hollow new york

Rockefeller State Park Preserve

This huge park is comprised of 1,400 acres, so it’s the perfect place to explore and experience the great outdoor! In the summer it’s perfect for hiking, running, bird watching, fishing, picnicking, horseback riding, carriage driving, photography, painting, geocaching (park permit required). You name it – there is SO MUCH you can do in this part of Sleepy Hollow!

With plenty of spots for a lovely picnic, it’s a great choice for that long-awaited family day out. 


Listen to some jazz music

If you’re a music fan (and specifically into jazz) then you’re going to love the Jazz Forum, (located at 1 Dixon Lane, Tarrytown). It’s a venue known for amazing music and jazz, and it’s constantly hosting amazing performers and putting on incredible shows. It’s an intimate venue (only 100 people!) so it’s a really special music experience to have during your time in Sleepy Hollow.

You’ll find the headline jazz artists on Fridays and Saturdays, and celebrated Brazilian groups on Sundays. It’s definitely worth a visit, and you’ll love it.


Enjoy some theatre

Next on my list of things to do in Sleepy Hollow, New York, it’s theatre! The local theatre venue for Sleepy Hollow is the Tarrytown Music Hall online box office. You’ll find a load of different theatre performances at Tarrytown Music Hall, and there’s a big mix of talent and performers to choose from. If you’re really set on a specific kind of performance, it’s a great idea to check out their website (linked above) to see the listing s and schedule ahead of your trip. You can (very handily) but tickets through the online box office, or in person at the physical box office.


Headless Horseman Bridge

This famous bridge was written about many times (and used in movies) so it’s a must-see for anyone visiting Sleepy Hollow because of the literary roots!

headless horseman bridge things to do in sleepy hollow

Hopefully this list of things to do in Sleepy Hollow, New York has been useful!

There’s so much to do in Sleepy Hollow, so make sure you cram in as many of these suggestions as possible during your time there! Hopefully this list of things to do in Sleepy Hollow, New York has been useful and you’ve got plenty of ideas for your trip!

things to do in sleepy hollow new york.
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