Are you looking for the best things to do in Tarrytown, NY in the fall? We’ve got you covered!
Tarrytown, New York, is set against the backdrop of the Hudson River and is gorgeous in the fall!
And since it’s only about an hour north of Manhattan, it’s a popular tourist destination for a fall weekend getaway or even a week away.
Tarrytown and the surrounding towns, like the infamous Sleepy Hollow, capitalize on their legends and ghost stories to make this area a must-visit destination in October and November.
When we visited, we loved the the Great Jack O’Lantern Blaze and learning more about Washington Irving, the author of The Legend of Sleepy Hollow.
However, Tarrytown offers more than frights! The guide below shares about the fun things to do in Tarrytown and nearby in the fall.
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15 Fun Things to Do in Tarrytown in the Fall
1. Sunnyside
The man who put the Hudson River Valley on the map is none other than Washington Irving.
Lauded for being the first American author to set his stories in America (like Rip Van Winkle in the Catskill Mountains), his famous tales have brought visitors to the area for years. It is only fitting that his home, Sunnyside, is also a draw to tourists.
Located on the banks of the Hudson River in Irvington, NY, the Historic Hudson Valley offers tours of the Sunnyside. They also host various events throughout the year.
During the fall months, visitors get a “spooky” tour of the home, which incorporates information about seances and vampires. The tours are still family-friendly, as are the activities that are included with your ticket!
2. Union Church of Pocantico Hills
Another active church in the Hudson River Valley, Union Church, was built in 1921 by John D. Rockefeller. The church is open to visitors Thursday-Sunday with varying hours.
One of the biggest draws of the church is the Rose Window, created by artist Henri Matisse. As the church is still active, you can also attend a Sunday sermon!
3. Philipsburg Manor
One of the oldest standing buildings in the area, Philipsburg Manor in Sleepy Hollow, was owned by the Philipse family. The Philipse family were extremely wealthy and owned most of the land in West Chester County.
Today, tours are offered of the home by Historic Hudson Valley. The tour includes learning what life was like for the enslaved people who primarily lived on and ran the plantation, as well as the various medical treatments of the time.
Timed tours last approximately 1.5 – 2 hours, so plan your day accordingly. Tour times vary, but are generally offered mid-May through mid-December.
4. Kykuit, the Rockefeller Estate
This century-old building owned by John D. Rockefeller is still an active home of the Rockefeller family. The Historic Hudson Valley holds tours of Kykuit and its grounds.
There are multiple tours offered that span from 1.5 – 3 hours, which includes transportation to and from the visitor center. Some of the tours are of the Kykuit mansion, while others are of the grounds and gardens.
You can visit the estate from the beginning of May until Veteran’s Day Weekend in November. The tours leave from the Philipsburg Manor visitor center. Please note, children under 5 years old are not permitted on the tours.
5. The Old Dutch Church
Right next to Philipsburg Manor is the Old Dutch Church. Designed and commissioned by Frederick Philipse for his tenants, the church is one of the oldest in the United States. It also played a prominent role in Washington Irving’s The Legend of Sleepy Hollow.
The Old Dutch Church in Sleepy Hollow is an active church. You can walk the grounds for FREE, or step inside for a Sunday sermon. During select days and nights in October, you can attend a performance of The Legend of Sleepy Hollow at the church.
6. Lyndhurst Mansion
Designed in 1838, the Lyndhurst Mansion sits on 67 acres along the Hudson River.
They offer various tours of the mansion. However, the tours are not recommended for children under 5 years old. Also to note, strollers are not allowed inside the mansion.
The grounds are available to tour on your own. There is a $10 per person fee and you must reserve passes ahead of time.
7. The Tarrytown and Sleepy Hollow Farmer’s Market
On a beautiful fall weekend, there is nothing like spending some time outside! A great place to start is the Tarrytown and Sleepy Hollow Farmer’s Market.
The market runs from Memorial Day Weekend through Thanksgiving and offers an array of fresh foods and good music!
Kids will love the area as there is a large playground adjacent to the market, as well as a fun bridge and tunnel to explore.
Additionally, the market is held in Patriot’s Park. This location holds historical significance, as it is where British General John Andre was captured during the American Revolution!
8. The Old Croton Aqueduct Trail
In the mid-19th century, a 41-mile underground aqueduct was constructed to bring fresh water from the Croton River to New York City.
Its use continued until 1965, and then, in 1968, the New York State Office of Parks, Recreation, and Historic Preservation purchased 26.2 miles of the trail to preserve as the Old Croton Aqueduct Trail.
The trail starts at the New Croton Reservoir and runs through the City of Yonkers in New York. Visitors can pick up the path and enjoy a leisurely walk while learning some history along the way.
Some notable sightings along the trail include the double arch, located across from the Ossining Museum, and Kykuit, the Rockefeller’s estate.
9. The Westchester RiverWalk
The Westchester RiverWalk is a planned pathway that follows the Hudson River through the various towns along the waterway.
There are a few completed sections in Tarrytown and also in nearby Croton-On-Hudson. Along the path are several signs with information about the history of the area and the ecology.
It’s one of the best things to do in Tarrytown in the fall because you’ll have beautiful views of the Mario Cuomo Bridge over the Hudson River with the gorgeous fall foliage in the background.
10. Rockefeller State Park Preserve
You’ll find plenty of things to do in this 1775-acre park near Tarrytown. The Rockefeller State Park Preserve boasts a few dozen trails (most are less than 1 mile long) and are easy enough for most people.
Try the 13 Bridges Trail for a nice 2-mile walk over thirteen bridges along carriage roads that were constructed in the 1920s and 30s. Or the Rockwood Hall Trail, with beautiful views of the Hudson River.
11. The Headless Horseman Sculpture and Bridge
While you are visited Philipsburg Manor or the Old Dutch Church, make a point to cross the Headless Horseman Bridge and see the sculpture dedicated to the famous antagonist.
While it is not the original covered bridge as depicted in the story, it is the area that inspired Washington Irving’s The Legend of Sleepy Hollow!
12. The Sleepy Hollow Cemetery
Speaking of Washington Irving, you can pay your respects to the American author at the Sleepy Hollow Cemetery.
The cemetery is located adjacent to the Old Dutch Church, though not affiliated with the church. The cemetery is home to many famous people, including Washington Irving, Andrew Carnegie, Elizabeth Arden, and Walter Chrysler.
You can visit the Sleepy Hollow Cemetery for FREE and use a map to take a self-guided tour. Or you can choose one of the many offered tours, including day-time tours, or night-time lantern tours.
13. The Great Jack O’Lantern Blaze
This family-friendly event at the Van Cortlandt Manor in Croton-on-Hudson is a must-see and definitely our favorite thing to do in Tarrytown in the fall! Over 7000 Jack O’Lanterns are carved and lit to create unique and fun sculptures.
The Great Jack O’Lantern Blaze runs weekends from mid-September through November and weekly during October.
14. Horseman’s Hollow at Philipsburg Manor
Philipsburg Manor is fun to visit during the day, but on weekend nights during the month of October, it is transformed into the 18th-century village featured in The Legend of Sleepy Hollow.
Horseman’s Hollow is the most-popular scary event hosted by the Historic Hudson Valley. Timed tickets are available for purchase online!
15. The Sleepy Hollow Experience
Visitors can watch the story of The Legend of Sleepy Hollow play out in front of their eyes at the immersive theatrical experience. The Sleepy Hollow Experience is held at Washington Irving’s Sunnyside.
Visitors will meet Ichabod Crane, party with the Van Tassels, and meet the Headless Horseman himself during the performance. It is a unique opportunity to be surrounded by the tale at the place where it was created!
Best Restaurants in Tarrytown, NY
- Bridge View Tavern: Typical pub fare serving sandwiches, tacos, and salads with a gorgeous view of the Hudson River and Mario Cuomo Bridge.
- Horsefeathers: A varied menu with options like burgers, sandwiches, and other comfort foods.
- Beekman Ale House: Delicious pizza restaurant also serving homemade meatballs and fried mozzarella.
Where to Stay in Tarrytown, New York
Many of the major hotel chains, including Hilton, Marriott, and Wyndham have hotels within close driving distance to all of the attractions we share.
We stayed at the Hampton Inn Whiteplains/Tarrytown and had a great experience. The rooms were clean and comfortable, and the included breakfast had an assortment of both hot and cold foods.
For a more luxurious retreat, you can stay in a real castle at the Castle Hotel & Spa.
Getting to Tarrytown, New York
By Car
Tarrytown, NY, and its neighboring villages are easily accessible thanks to the famous Mario Cuomo Bridge (formerly the Tappan Zee) that crosses the Hudson River.
About an hour north of New York City, Tarrytown is also a short drive from Philadelphia and Boston, making it the perfect weekend getaway destination.
By Train
Tarrytown is easily accessible by the MTA’s Metro-North Railroad on the Hudson Line. The line also stops at Irvington and Philipse Manor in Sleepy Hollow.
Other Places in New York to Visit in the Fall
Although many people only think of New York City when they think of New York, the state itself offers so many amazing things to do to enjoy the fall weather and changing leaves. These are some other New York locations that are perfect for a fall getaway.
- There are so many things to do in the Catskills that are ideal in the fall. We loved the nature trail to the Saugerties Lighthouse and also visiting the unique sculpture park, Opus40.
- Hike the waterfall trails in the Finger Lakes before they close for the winter.
- Early fall is one of the best times to visit Rochester
Wrapping Up Things to Do in Tarrytown in the Fall
The Hudson River Valley is absolutely gorgeous anytime of year, but we think it’s extra beautiful in the fall.
There are so many ways you can enjoy the beauty of the season by walking around town, enjoying the Hudson Riverwalk, and taking a hike on one of the many trails in Rockefeller State Park Preserve.
We love the seasonal events, especially the Great Jack O’Lantern Blaze. This event is a can’t miss!
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