If you’re looking for a quick getaway from the bustle of New York City, the villages of Tarrytown and Sleepy Hollow (just under an hour away) are the perfect options for a quick southern Hudson Valley day trip.
While visiting New York City, my family and I decided to take advantage of Hudson Valley’s proximity and delve into the charming villages for a day. Even if it’s just you and your sweetheart, these are also romantic things to do in the Hudson Valley. Here’s what you can expect from the history-filled day trip to Tarrytown and Sleepy Hollow.
Please keep in mind these details are subject to change. Due to COVID-19, social distancing and face coverings may be required. Be sure to check local health officials’ safety regulations and each establishment’s website for updated information before making final plans.
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Tarrytown & Sleepy Hollow: A Hudson Valley Itinerary
Map of Sleepy Hollow and Tarrytown Itinerary
Tarrytown, New York
Located 25 miles (40 km) north of New York City on the eastern shore of the Hudson River, the hilly Village of Tarrytown can bring a great change of pace for a day or even longer. Like most Northeastern towns, it is stacked with lovely heritage buildings, picturesque riverside views, beautiful green space, and history from Native Americans through European colonization and 20th-century industrialization.
How to Get to Tarrytown
Taking the Metro-North train from Grand Central Station to the Tarrytown stop, you can expect a travel time of just short of an hour. Tickets are priced by peak and off-peak times. And it is suggested that you purchase your tickets online or at the station before departure to secure the most favorable prices. Driving offers a couple of options.
Things to Do in Tarrytown, New York
Main Street Tarrytown
We started our journey near Westchester County’s oldest theater, the Tarrytown Music Hall. The historic theatre built before 1900, continues to line up entertainment acts including comedy shows, jazz, blues, country, and rock bands.
Conveniently located on Tarrytown Main Street, the theatre is surrounded by commercial businesses and offers a wide selection of restaurants from basic burgers joints to ethnic, organic, and sustainable options.
Tarrytown has an upscale colorful vibe. Walking along the shopping district, you’ll also find trendy boutiques, galleries, and numerous antique shops.
Scenic Hudson RiverWalk
Just under a mile downhill from Main Street toward the Tarrytown Metro-North train station, and right along the water’s edge at Pierson Park, lies the Scenic Hudson RiverWalk.
We spent quite a bit of time here taking in the sweeping views spanning from Manhattan to Governor Mario M. Cuomo Bridge. The riverfront park also includes a stretch of lush green space filled with native plants, a playground, picnic pavilion, benches and tennis, and basketball courts. It’s an ideal spot to unwind and watch the sunset over the river.
Purchased by John D. Rockefeller in the mid-20th Century, he fulfilled his ambition to preserve the home as a historic landmark. The Historic Hudson Valley now operates the restored home containing original furniture and accessories. But note, photography of any type is prohibited.
Address: 3 W Sunnyside Ln, Irvington, NY 10533
This 67-acre estate is more of a castle than an ordinary house. The 1838 Gothic Revival mansion, once owned by railroad tycoon Jay Gould, still contains original furnishings collected by its three owners.
Be sure to check out the conservatory, the first of its kind to be reinforced with steel framing. And end the experience with a stroll through the grounds to visit the bowling alley or Rose Cottage. See Lyndhurst.org for tour schedules and special events.
Address: 635 S Broadway, Tarrytown, NY 10591
Other Mansions – At the turn of the 19th to the 20th century, Tarrytown was a hub for millionaires. Many of their estates remain today.
- Carrollcliffe, now the Castle Hotel & Spa is built in the Tudor style from stone quarried from the property on which it stands. Initially, there were 45 rooms on a 64-acre plot. Address: 400 Benedict Ave, Tarrytown, NY 10591
- Hillcrest was constructed in 1882, Mark Twain purchased the property in 1902 and lived there for two years. In 1915 the original structure was demolished and rebuilt in a more solid form, renaming it Halleston. Undergoing another change during World War II, it is now known as Tappan Hill and is popular for weddings and galas. Address: 81 Highland Ave, Tarrytown, NY 10591
Sleepy Hollow, New York
Formerly known as North Tarrytown, Sleepy Hollow is a mecca for Washington Irving fans. The town has several historic sites plus a nearby state park.
How to Get to Sleepy Hollow
Use the Metro-North Railroad (Hudson Line) to the Sleepy Hollow Philipse Manor Station. While it may seem easier to purchase your tickets on board the train, there is a significant price increase for this convenience. To avoid this, buy tickets online, at the station window, or using the vending machines. Some of the local hotels offer shuttle services to and from the station.
Things to Do in Sleepy Hollow, New York
Sleepy Hollow Cemetery
Sleepy Hollow Cemetery is the final resting place of writer Washington Irving and several famous figures including Andrew Carnegie, Walter Chrysler, Elizabeth Arden, and Leona Helmsley.
A free self-guided tour map is available at the cemetery office or the south gate, adjacent to the Old Dutch Church. For guided tours and special events, visit the Sleepy Hollow Cemetery website for more information.
Address: 540 N Broadway, Sleepy Hollow, NY 10591
Old Dutch Reformer Church and Burying Grounds
Not to be confused with the nearby Sleepy Hollow Cemetery, this is the final resting place of locals who may have inspired Washington Irving. Only self-guided tours are available but be aware that the gates are locked at 4:30 p.m., so don’t get caught inside or you may experience a visit by the Headless Horseman.
Don’t know what we’re talking about? Watch the Sleepy Hollow film adaptation for FREE with an Amazon Prime membership.
Address: 430 Broadway, Sleepy Hollow, NY 10591
Kykuit, the Rockefeller Estate
Kykuit was home to several generations of Rockefellers during the heyday of millionaires finding refuge in the quiet countryside. The 6-story estate has outstanding views of the Hudson River and is filled with artwork, as well as fountains, gardens, and a collection of antique cars and horse-drawn carriages. It is now a historic site with guided tours available through Historic Hudson Valley.
Address: 381 N Broadway, Sleepy Hollow, NY 10591
Today the Philipsburg Manor is a tribute to the grueling work performed by slaves of African descent. The gristmill and manor house are open to the public and offer a view of the lifestyle of the Philipse household as told by guides in period costume.
Address: 381 N Broadway, Sleepy Hollow, NY 10591
1883 Lighthouse – Sleepy Hollow Lighthouse
Also known as the Kingsland Point Lighthouse and the Tarrytown Lighthouse, it operated for over 78 years. It was automated in the mid-20th century but continued in operation until decommissioned by the federal government in 1961. The village of Sleepy Hollow offers tours of the cast-iron structure.
Address: Tarrytown Light-Kingsland Point Path, Sleepy Hollow, NY 10591
Halloween in Sleepy Hollow – Great Jack O’Lantern Blaze
If you’re looking for an epic Halloween event, consider planning your trip to Sleepy Hollow in the fall to coincide with the Great Jack O’Lantern Blaze event. This should be #1 on your list.
From the end of September through Halloween night, take a spooky walk complete with over 7,000 hand-carved jack o’ lanterns beautifully illuminating along the riverside near Van Cortlandt Manor.
Listen to creepy Halloween tales, take a tour of the Museum of Pumpkin Art, stargaze inside the Pumpkin Planetarium. Don’t miss the Pumpkin Carousel and a 25-foot-tall jack o’lantern Statue of Liberty. Plan ahead because tickets tend to run out fast.
Address: Van Cortlandt Manor, 525 S Riverside, Croton-on-Hudson, NY 10520
Where to Stay in Sleepy Hollow and Tarrytown
If you’re in the area for more than a day, here are a few accommodations with varying budgets.
Treat yourself to the Castle Hotel & Spa, a spectacular hotel sporting the best views of the city with packages ranging from delicious breakfasts and glorious massages. Check rates and availability here!
Doubletree Hotel Tarrytown offers all the amenities from an indoor pool, a 24-hour fitness center, all within the vicinity of the attractions you want to hit up on your list. Check rates and availability here!
Hampton Inn White Plains
Features comfortable modern room, outdoor pool, and onsite fitness center.
Hudson Valley Campgrounds Near Sleepy Hollow and Tarrytown
Why not camp outdoors during your trip to Tarrytown & Sleepy Hollow? It’s an experience to lie under the stars, build a campfire, and share stories with your family. Here are a few campgrounds. Don’t forget to look into the rules and regulations of the grounds.
Where to Eat in Tarrytown and Sleepy Hollow
From a good cup of coffee to a light lunch or hearty dinner, there are a number of eateries in Tarry town and Sleepy Hollow. An eclectic mix of nationalities, including Greek, Portuguese, Indian, Moroccan, etc., offer you a wide choice of taste sensations to top off your visit. Here are a few local favs:
- Equus: A fine dining restaurant at the Castle Hotel & Spa with a magnificent Sunday brunch.
- Blue Hill at Stone Barns: A farm-to-table cuisine restaurant offering lunch and dinner.
- Lefteris Gyro: An amazing casual Greek food spot with a welcoming staff.
- Sleepy Hollow Tarrytown Farmers Market – The TaSH: A community-run market with loads of farm-fresh local food. Find everything that you need in the way of snacks.
So, here’s hoping that this information stirs some wanderlust and you enjoy a quick history-filled day trip out of the city.