Are you looking for things to do in Sleepy Hollow, New York? Keep reading for my recommendations!
If you’re looking for things to do in Sleepy Hollow, then you’ve come to the right place!
Sleepy Hollow in New York is a great place to visit for a weekend out of 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 travelers will enjoy no matter their age, as there are so many things to do in Sleepy Hollow!
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 activities 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.
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.
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Have dinner in a castle
Next on our list of things to do in Sleepy Hollow, it’s a special dinner!
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!
Philipsburg Manor is next on our list of things to do in Sleepy Hollow.
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.
New York according to both locals and tourists, this manor just had to make it onto our list!
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!
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Headless Horseman Monument
Next on my list of things to do in Sleepy Hollow, New York, it’s the spooky 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 attractions in Sleepy Hollow, 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!
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Kykuit is the next suggestion on my list. One of America’s most famous private residences, Kykuit: The Rockefeller Estate is a great way to spend the day in Sleepy Hollow.
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.
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Visitors can take guided tours of the property and hear stories about the Rockefeller family as they make their way round the property!
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!) because this is the perfect choice for things to do in Sleepy Hollow for you!
Though this isn’t technically in Sleepy Hollow (you’ll need to drive around 20 minutes to reach Croton-on-Hudson).
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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! 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…
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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 choice for nature lovers too.
Take a stroll around Tarrytown
Next on our list of things to do in Sleepy Hollow, it’s 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.
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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 visitors, and the perfect way to end a day of sightseeing too.
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… But this is definitely one of the best things to do in Sleepy Hollow during Halloween and spooky season!
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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 well worth visiting and I think you’ll be fascinated by the place.
Though the cemetery is probably the main attraction here, the adjoining church is certainly worth a look!
Who doesn’t love a castle? If you’re looking to see where some of your favorite 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, if you’re looking to indulge your inner architecture nerd, this is the place.
Trust us, this place is stunning.
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 chance 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 on this list, and it’s a chance to enjoy the great outdoors and the beautiful scenery!
Head out during sunrise or sunset for super gorgeous views.
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, and that’s definitely half the fun. I always like having a bit of a contest with my husband or friends, to see who can find the ‘weirdest’ item.
Or maybe the most haunted item!
Here are some of my top picks for antique shopping in Sleepy Hollow:
- Belkind Bigi
- Canfin Gallery
- Michael Christopher Antiques
- Carol Master Antiques
- Pretty Funny Vintage Antiques & Curious Goods
- Cherry Door Thrift Shop
Rockefeller State Park Preserve
The Rockefeller State Park Reserve is our next suggestion for things to do in Sleepy Hollow.
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, and 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
Next up, on our list of things to do in Sleepy Hollow, it’s listening 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, especially if you fancy a night out!
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Enjoy some theatre
Next on my list of things to do in Sleepy Hollow, New York, it’s the theater!
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!
We couldn’t really write a list of things to do in Sleepy Hollow without mentioning this local spot.
It’s a classic photo opportunity in the town, and you have to grab at least one selfie with it.
Hopefully this list 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!