10 Things To Do In Tarrytown: Complete Guide To New York's Scenic Upstate Village

Jul 10, 2023

New York has tons of places to explore, but Tarrytown is a unique destination with a long list of interesting things to do and see.

Nestled along the eastern bank of the Hudson River, approximately 25 miles north of Midtown Manhattan, Tarrytown beckons as a picturesque haven within New York's Westchester County. This quaint village, part of the town of Greenburgh, boasts a rich history reflected in its skyline adorned with castle mansions—a legacy from its "Millionaire's Colony" era.

Forbes' accolade as one of the United States' loveliest towns is well-earned, as Tarrytown offers enchanting river views, a charming, walkable village center studded with boutiques and cafés, a convenient 35-minute express train ride to Manhattan, proximity to waterfront developments, and the allure of the Hudson RiverWalk park. Heading into autumn, Tarrytown is one of the many towns in Upstate New York to see fall leaves and experience the crisp weather. Of course, it's also an appealing destination to visit year-round.

This comprehensive guide unveils ten captivating things to experience in Tarrytown, inviting travelers to discover this Upstate gem's scenic splendor and cultural allure. There are many small charming towns in Upstate New York, but none like Tarrytown.

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One of the first sights to see in the Tarrytown, New York, area is the Lyndhurst Mansion. Here lies a stunning historic landmark, originally built in 1838. Lyndhurst, also known as the Jay Gould estate, is a Gothic Revival country house in its own 67-acre park beside the Hudson River, making it the perfect day trip in Upstate New York.

The next thing to do in Tarrytown is to visit Washington Irving's Sunnyside, a historic house on 10 acres along the Hudson River. Here lies a landmark home of the American author Washington Irving, best known for his short stories, such as "Rip Van Winkle" and "The Legend of Sleepy Hollow."

Another idea for Tarrytown, NY, guests is to walk along the Scenic Hudson RiverWalk Park. Here is a public trail space and park where everyone can soak up the sun (or feel the fall breeze) while in Tarrytown. It's filled with runners, pets, and nature, so give it a shot the next time you're in the area!

A tour of the towns along the Hudson Valley in New York is an excellent way to spend time in the state.

The next thing to do in Tarrytown is to drive across the famed Tappan Zee Bridge, officially named the Governor Mario M. Cuomo Bridge after the former New York governor. Here is where a twin cable-stayed bridge spanning the Tappan Zee section of the Hudson River between Tarrytown and Nyack, NY, spans just 20 miles north of NYC.

As one of the most visited attractions/landmarks in Tarrytown, the Sleepy Hollow Lighthouse is one to see. Standing 60 feet tall and loaded with history, this lighthouse has been a staple of the community for decades. It is a conical steel structure erected in the 1880s. In 1979, it was listed on the National Register of Historic Places.

For those wanting to soak up the sun in Tarrytown, heading to Patriots Park is a nice idea. Here, tourists can explore the property, located on U.S. Route 9 along the boundary between Tarrytown and Sleepy Hollow in Westchester County, New York. It's four acres and perfectly charming.

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Sleepy Hollow (the other side of Tarrytown) is extra spooky around Halloween, which could make it a nice stop for a fall trip to the area.

Another sight to see in Tarrytown is the beautiful Music Hall. Here lies the brick structure in the Queen Anne architectural style erected in the late 19th century, which sits in the downtown area.

Shows are regularly performed here, so keep an eye on the website for updates.

The next thing to do is head to what once was considered Tarrytown but now goes by Sleepy Hollow. This is a magical village in Upstate New York that is known for its beauty, charm, and friendly residents.

Notably, Sleepy Hollow is known for being known as the setting of Washington Irving’s “The Legend of Sleepy Hollow.” This is the perfect day trip and should be fun around the holidays.

Located just beside Tarrytown lies the stunning Rockefeller State Park Preserve. This is a state-owned park where the public can come and enjoy the scenery 24 hours a day.

Rockefeller State Park Preserve is a state park in Mount Pleasant, New York, in the eastern foothills of the Hudson River, and boasts many trails for guests.

Lastly, we have the iconic Philipsburg Manor, located just outside Tarrytown in Sleepy Hollow. This location is said to be haunted, with a rich past leading back to the later 1600s.

Additionally, visitors can cross the millpond bridge to Philipsburg Manor, a mill and trading complex where an enslaved community lived and labored for generations.

Regarding the best time to visit Tarrytown, this is in the fall and the summer. Most activities fall between mid-June to late September, making that 'prime' time to visit. However, any time of the year should prove stunning in Upstate New York, especially if someone loves the outdoors.

When it comes to getting around Tarrytown and the Upstate New York area, a private vehicle is required. Unlike in New York City, where cabs rule the streets, Tarrytown is far smaller and remote. Therefore, tourists to the region should bet on renting a vehicle or requesting an Uber/Lyft in advance.

Luckily, there are private car services to use in Tarrytown, but it will be cheaper to rent one yourself at a company like Hertz, etc.

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For those hungry and thirsty during their vacation, Tarrytown offers plenty of restaurants, bars, and hole-in-the-wall establishments. Here are some ideas for breakfast, lunch, dinner, and drinks in Tarrytown.

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For hotels in Tarrytown or nearby, there are some options for tourists. Here are some we've found to fit everyone's budget.

Regarding tips for those coming to Tarrytown or the Hudson Valley Region of New York, there are things to remember. First, these towns and villages are small and require a car to get between them.

It's also worth noting that hotels, inns, and rentals can book up during holidays, especially if it's peak vacation season. Summer and fall is the best time to come here, but spring and winter also bring their own set of pros.

Also, remember to shop small and support local businesses throughout this charming region.

For those in Tarrytown wanting to try something new, it could be fun to head to historic places, like the Lyndhurst Mansion and Sleepy Hollow Lighthouse, or even walk along the Hudson River. Tarrytown is filled with places to explore, so don't be nervous to take a few detours!

Grab lunch in town and head to Sleepy Hollow for an afternoon of fun and enchantment. From there, return to the hotel, order room service, and do it all again tomorrow. Have fun!

Noah is a full-time content creator, writing mainly in travel, home, garden, DIY, music, and finance niches. If there's a story to be told: Noah will find it. A day at the computer, plenty of words written, and a polished, fact-heavy piece are Noah's specialties. Helping the world, one word at a time.