Top Things to Do in Sleepy Hollow, NY: Ultimate 2-Day Itinerary

If you’ve ever dreamed of stepping into a Halloween town straight out of a storybook, Sleepy Hollow, New York should be at the top of your fall bucket list. Nestled on the banks of the Hudson River and just a short drive from New York City, this charming village is best known for its haunting folklore especially The Legend of Sleepy Hollow by Washington Irving. And let me tell you, this place fully embraces its ghostly roots.

I visited Sleepy Hollow in October, and the entire town felt like a cozy mix of history, autumn magic, and just the right amount of eerie. From candlelit cemetery tours and centuries-old churches to pumpkin-lined paths and haunted hayrides, there’s no shortage of things to do. The town’s historical significance, especially spots like the Old Dutch Church and Sleepy Hollow Cemetery, is fascinating even if you’re not a huge history buff.

But heads up- October is peak season here. Nearly 100,000 people visit during the Halloween month alone, so expect heavy crowds, sold-out events, and limited parking. If you’re planning a fall weekend getaway, definitely book your accommodations and tickets in advance.

I also explored nearby Tarrytown, which is just minutes away and offers even more charming streets, historic homes, and waterfront views. Between the autumn foliage, the festive atmosphere, and the spooky legends, Sleepy Hollow is an unforgettable destination especially if you’re a fan of Halloween or looking for a unique weekend escape in the Hudson Valley.

In this blog, I’ll share everything you need to plan the perfect two-day itinerary in Sleepy Hollow, including how to get there, where to stay, the best haunted attractions, scenic walks, seasonal events, great food spots, and family-friendly activities. Whether you’re visiting with kids, your partner, or flying solo with a love for legends, this guide has you covered.

Best Time to Visit

The best time to visit Sleepy Hollow is hands-down October, when the town is bursting with fall colors, Halloween events, and spooky charm. This is when Sleepy Hollow truly comes alive but it’s also the busiest time, so expect crowds and book everything early. If you prefer a quieter visit with milder weather, late September or early November offers a similar vibe without the packed streets.

Day 1: Historical Haunts and Scenic Strolls

Breakfast in Sleepy Hollow

Start your day off right with a cozy breakfast in or near Sleepy Hollow. Horsefeathers in Tarrytown is a local favorite with hearty options and a quirky vibe. Coffee Labs Roasters is perfect for a quick bite and great coffee. If you have a sweet tooth, The Bakehouse at Tarrytown has fresh pastries and river views.

Visit the Sleepy Hollow Cemetery

Sleepy Hollow Cemetery is a great place to begin your adventure. Get there when the gates open at 8 a.m. and you’ll have the place almost to yourself. The main entrance by the Old Dutch Church is the easiest place to park. Some side entrances might be locked or harder to get to, so it’s best to stick with the main lot. Arrive early, because that lot is pretty small.

Walking through the cemetery is the way to experience its history and eerie charm. You can drive through some sections, but you’ll miss out on the old mausoleums, peaceful wooded trails and the graves of famous folks like Washington Irving the author who put Sleepy Hollow on the map. It’s quiet, reflective and a little mysterious—a great way to start your day.

Explore the Old Dutch Church and Burial Grounds

The Old Dutch Church and burial grounds are just steps from the cemetery. That church, built in 1685, is a big deal in American folklore. It’s the church from Washington Irving’s The Legend of Sleepy Hollow and the Headless Horseman’s ghostly ride begins somewhere nearby.

The burial ground around the church is a 2.5-acre patch of weathered headstones some of which date back centuries. It’s a peaceful, atmospheric spot that’s full of history. If you love literature or just old, haunted places, this is a must-see.

Philipsburg Manor: Step Back in Time

After exploring the church and cemetery, head over to the Philipsburg Manor Visitor Center. It’s just a short drive away and well worth the visit. This beautifully restored 18th-century estate lets you experience what life was like back then, complete with costumed interpreters and working mills.

Before you go inside, stop by the Headless Horseman Monument. That stone monument, erected in 1974, captures one of the most iconic moments from The Legend of Sleepy Hollow. It’s a great photo op and adds a fun, spooky touch to your journey through the village’s legendary past.

Dinner Recommendations (Family-Friendly & Romantic Options)

After a full day of exploring Sleepy Hollow, you’ll definitely be ready for a good meal. If you’re traveling with family, check out Bridge View Tavern it’s casual, kid-friendly, and serves up delicious burgers, BBQ, and local brews with views of the Hudson. Another great pick is Horsefeathers in nearby Tarrytown, known for its fun vibe and broad menu.

Looking for something more intimate? Sweet Grass Grill in Tarrytown is perfect for a cozy, locally-sourced dinner with a warm ambiance. For a romantic waterfront setting, head to Hudson Farmer & the Fish, where you can enjoy fresh seafood while watching the sun set over the river.

Evening Ghost Tour or Lantern Tour

My favorite part of visiting Sleepy Hollow was ending the day with a ghost tour by lantern light. As the sun went down and the shadows stretched across the gravestones, the whole town got even spookier and trust me, walking through the cemetery at night with only lanterns to guide you? Chills.

The tour guide shared local legends, real historical facts and stories about the people buried there — including some very creepy tales tied to Washington Irving’s Legend of Sleepy Hollow. Not over-the-top scary but definitely that creepy-but-fascinating vibe that makes you glance over your shoulder now and then.

If you visit in October these tours sell out fast so book ahead. It’s the perfect way to wrap up your day and feel like you’ve really experienced the heart (and haunt) of Sleepy Hollow.

Day 2: Legends, Nature, and Culture

Morning Coffee and Light Bites

Start your second day in Sleepy Hollow with a warm cup of coffee and a light breakfast. For a cozy spot The Coffee Labs Roasters in Tarrytown has freshly brewed coffee and delicious pastries — perfect for fueling up before your outdoor adventures. If you’re looking for something heartier The Bakehouse at Tarrytown has breakfast sandwiches and pastries with a charming atmosphere and river views.

Rockefeller State Park Preserve (Hiking & Birdwatching)

After your morning coffee head to the Rockefeller State Park Preserve where you can get into nature. With over 1,000 acres of woods, ponds and trails this is a haven for hiking, birdwatching and outdoor enthusiasts. I loved walking the Pond View Trail where you’ll often see ducks, herons and other wildlife along the way.

If you’re up for more adventure the trails range from easy walks to more challenging hikes. The park is also perfect for a picnic by the water so bring some snacks if you want to enjoy the peace and quiet of the outdoors. Whether you’re an avid hiker or just looking for a leisurely walk this park is a must visit for a quiet nature break.

Lyndhurst Mansion or Kykuit: The Rockefeller Estate

Just a 15 minute drive from the Union Church is the Lyndhurst Mansion, a beautiful example of Gothic Revival architecture right on the Hudson River. Built in 1838 this grand estate has pointed arches, turrets and intricate details that look like a fairytale come to life.

The grounds are just as impressive with river views. One of the highlights is the billiards building which even has its own bowling alley- how cool is that? Whether you’re into history, architecture or just want to wander the beautiful estate Lyndhurst has it all.

After exploring the historic landmarks, take some time to wander through Tarrytown’s charming streets, where you’ll find local art galleries and unique boutiques showcasing everything from paintings and sculptures to handmade jewelry and vintage finds.

I stumbled upon The Blue Door Gallery, which had a collection of local artists’ work that really captured the spirit of the Hudson Valley. Whether you’re looking for a souvenir or simply want to appreciate the local art scene, this is the perfect place to spend an hour or two.

Lunch with a View

For lunch, nothing beats dining with a view of the Hudson River. Head to The Tarrytown House Estate or The Hudson Farmer & the Fish for a relaxed meal while enjoying the scenic beauty around you. I loved sitting outside, savoring fresh, locally-sourced dishes, and watching the boats glide by.

Whether you’re in the mood for a casual bite or a more refined dining experience, both spots offer a beautiful setting that makes your lunch feel extra special.

Horseman’s Hollow (If Visiting in Fall)

If you’re visiting in the fall, make sure to experience Horseman’s Hollow, one of the most thrilling and spooky events Sleepy Hollow has to offer. Held at the Phillipsburg Manor, this haunted attraction brings Washington Irving’s Legend of Sleepy Hollow to life in a terrifying way.

Walk through the eerie grounds and encounter actors dressed as the Headless Horseman and other characters from the tale. It’s a must-see for anyone looking for some spooky Halloween fun, but be prepared for a good scare!

Sunset at Kingsland Point Park

End your day with a peaceful moment at Kingsland Point Park, a perfect spot to catch the sunset over the Hudson River. The park offers scenic views of the river and the surrounding hills, making it an ideal place to unwind.

Grab a bench or take a stroll along the riverbank and watch the colors of the sky change as the sun dips below the horizon. It’s a tranquil escape after a busy day of sightseeing, and a beautiful way to wrap up your time in Sleepy Hollow.

Seasonal Events & Festivals

Halloween Season in Sleepy Hollow

If you visit in October, you’re in for a treat. Sleepy Hollow during Halloween is like stepping into a storybook, especially if you love spooky. I got to experience Horseman’s Hollow and let me tell you, it was terrifying in the best way. Imagine walking through the dark, misty grounds of Phillipsburg Manor with actors dressed as the Headless Horseman and other characters popping out to scare you.

Plus the Great Jack O’Lantern Blaze is a must see the rows of glowing pumpkins create an atmosphere that’s both beautiful and eerie. If you’re a Halloween lover, this place is magic.

Summer Concerts and Farmers Markets

In the summer the town is so laid back and full of life. One of my favorite things to do was to wander through the Tarrytown Farmers Market where I picked up local produce, cheeses and homemade jams. It’s the perfect way to experience the local flavor (literally!) and the community vibe.

On weekends there are summer concerts in the park and it’s a great way to relax with a blanket on the grass, listening to live music while the sun sets. It’s one of those simple, feel good experiences you’ll remember long after your trip.

Winter & Holiday Events

Though I’ve only visited in the fall I can’t imagine how magical Sleepy Hollow must be during the holidays. I’ve heard from friends who visited during Victorian Christmas the streets are filled with holiday lights and it’s all so cozy and old timey.

Carriage rides through the snowy streets, festive markets and winter decorations make it feel like a holiday movie. If you want a more peaceful wintery atmosphere I’ve been told it’s the perfect time to visit.

Best Places to Eat in Sleepy Hollow

When it comes to food Sleepy Hollow may be a small town but it knows how to deliver. Whether you’re looking for a casual bite or a more refined dining experience there’s something for everyone.

Bridge View Tavern

If you’re looking for a laid back, family friendly spot with Hudson River views Bridge View Tavern is my top choice. Their menu is full of comfort food, burgers, fried chicken etc. I also loved their craft beers which fit the cozy vibe. It’s a great place to unwind after a day of exploring.

Horsefeathers

For a more lively atmosphere Horsefeathers in Tarrytown is a must see. It has a fun vibe and a broad menu to please everyone seafood, pasta etc. I found it to be a great place for dinner after a long day of sightseeing. The staff is super friendly and the atmosphere is warm and welcoming.

Sweet Grass Grill

For something a little more upscale but still casual enough for a relaxed evening, Sweet Grass Grill in Tarrytown is a fantastic choice. The food here is delicious, with a focus on locally sourced ingredients, and I loved how they incorporated Hudson Valley flavors into everything.

Their farm-to-table dishes are amazing, and it’s the kind of place that’s perfect for a romantic dinner or a special occasion.

The Hudson Farmer & the Fish

If you’re craving fresh seafood with an amazing view, head to The Hudson Farmer & the Fish. Located right on the river, this restaurant offers delicious, sustainably sourced seafood dishes, and the views of the Hudson are unbeatable. Whether you’re sitting indoors or enjoying the outdoor patio, it’s the ideal spot for a leisurely meal.

How to Get to Sleepy Hollow

Getting to Sleepy Hollow is easier than you might think, whether you’re driving from nearby cities or taking public transport. Here’s a quick guide:

By Car

If you’re coming from New York City, Sleepy Hollow is about a 40-minute drive up the Hudson River via I-87 North (the New York State Thruway) or I-287 West. The drive is beautiful, especially as you get closer to the river, and there’s plenty of parking around the main attractions. Just be aware, parking can fill up fast, especially in the fall, so plan accordingly.

By Train

For a stress-free trip, take the Metro-North Railroad from Grand Central Station in Manhattan. The Hudson Line will get you to Tarrytown Station in about 40 minutes. From there, it’s just a short 5-minute drive or a 20-minute walk to the heart of Sleepy Hollow. Trains run frequently throughout the day, making it a convenient option.

By Bus

If you’re coming from New York City, you can also take a Greyhound or Bee-Line bus to Tarrytown, then catch a local taxi or bus to Sleepy Hollow. It’s a more affordable option, though it may take a bit longer than driving or taking the train.

Where to Stay in Sleepy Hollow

Finding a place to stay in Sleepy Hollow is easier than you might think, and there are a few great options depending on the vibe you’re after.

Tarrytown House Estate

If you’re looking for a bit of history and charm, Tarrytown House Estate is an amazing option. Set on 26 acres of land, this beautiful estate overlooks the Hudson River, and the grounds feel like something out of a fairytale. I stayed here for a weekend getaway, and the setting was just perfect.

The rooms are spacious, and the hotel’s amenities, like the indoor pool and fitness center, really made it feel like a little retreat. It’s also just a short drive to all the key attractions in Sleepy Hollow.

Castle Hotel & Spa

For something a little more luxurious, the Castle Hotel & Spa in Tarrytown is a must-try. The place is literally a castle, and staying here feels like stepping into another era.

The views of the Hudson River from the hotel are breathtaking, especially at sunset. They also have a top-notch restaurant and a relaxing spa, so it’s perfect for a romantic getaway or anyone looking to pamper themselves a bit.

Sleepy Hollow Hotel

If you want to stay closer to Sleepy Hollow itself, the Sleepy Hollow Hotel is a great choice. It’s more modern and convenient, with a welcoming vibe that feels like home.

It’s located just a short drive from the major attractions in Sleepy Hollow, and the rooms are comfortable, with all the amenities you’d expect. I found it to be a great base for exploring the area, especially since they also have a nice bistro where you can grab a meal after a long day of sightseeing.

Courtyard by Marriott Tarrytown

If you’re looking for something straightforward and comfortable, the Courtyard by Marriott in Tarrytown is a solid choice. It’s nothing fancy, but it’s clean, modern, and well-located for easy access to both Sleepy Hollow and Tarrytown.

Day Trips from Sleepy Hollow

Tarrytown

Just a short drive from Sleepy Hollow, Tarrytown is a charming village worth exploring. I spent a few hours wandering around its historic downtown, where you’ll find quaint cafes, boutique shops, and cozy spots to relax. One of the highlights of Tarrytown is the Lyndhurst Mansion, a stunning Gothic Revival estate that’s open for tours.

It’s a peaceful place to visit, with beautiful grounds that overlook the Hudson River. If you have time, I’d recommend checking out the Tarrytown Music Hall for a show—it’s a historic venue with a great atmosphere.

Hudson Valley Vineyards (Optional Mention)

If you’re a fan of wine, consider taking a short drive to one of the nearby Hudson Valley vineyards. I visited a vineyard during my trip, and it was such a relaxing day. The views of the river and hills from the vineyard are gorgeous, and you can enjoy a wine tasting while soaking it all in.

There are a few good spots around, like Brotherhood Winery, which is the oldest in the country, or Whitecliff Vineyard, which has amazing views and a lovely patio for enjoying a glass of wine. If wine isn’t your thing, you can always opt for a more nature-filled experience.

Scenic Drives and Picnic Spots

If you want to enjoy the beautiful Hudson Valley without too much hustle and bustle, a scenic drive is the way to go. I took a drive along the Hudson River, and the views were absolutely breathtaking.

You can stop at places like Bear Mountain State Park for a picnic by the river or a hike if you’re up for it. Rockefeller State Park Preserve is another great spot to check out there are serene walking trails and peaceful meadows that make for a perfect picnic setting. Trust me, spending a quiet afternoon in these spots is the perfect way to unwind after a day of sightseeing.

Final Thoughts

After exploring Sleepy Hollow and immersing yourself in its history, you might want to continue your adventure to more stunning natural parks. For breathtaking landscapes and outdoor adventures, consider visiting Glacier National Park or Zion National Park. These iconic parks offer unforgettable experiences, from rugged mountains to lush valleys, providing the perfect blend of nature and tranquility.