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Points of Interest between Cheshire, Connecticut to Village of Pleasantville, New York

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picture of Cheshire, Connecticut

Best Things to Do on a Road Trip from Cheshire, CT to Pleasantville, NY

Cheshire, Connecticut and the Village of Pleasantville in New York are just over 100 miles apart, making for a perfect road trip. The journey will take travelers through scenic and historic towns, stunning natural beauty, and lots of attractions that guarantee a memorable experience. The halfway point of the trip is picturesque Bethel, CT, home to captivating landmarks like P.T. Barnum Square and the Matthew Curtiss House Museum.

Top 5 Things to Do:

1. Visit the Sleepy Hollow Cemetery

The Sleepy Hollow Cemetery is a major attraction in New York, located in the famous town of Tarrytown. A visit to this iconic site offers a chance to learn about the fascinating history of the area, thanks to the knowledgeable tour guides available. The cemetery is the final resting place of several notable individuals, including Andrew Carnegie, Walter Chrysler, Washington Irving, and William Rockefeller.

Interesting Fact: Sleepy Hollow is the inspiration behind Washington Irving's famous classic novel "The Legend of Sleepy Hollow."

2. Tour Kykuit, the Rockefeller Estate

Kykuit, also known as the Rockefeller Estate, is a lavish mansion with extensive gardens and stunning views. The estate has a rich history, having been home to four generations of the Rockefeller family. Visitors can indulge in a guided tour that takes them through the various rooms, revealing art collections, and sculptures. The site is a beautiful representation of the glorious affluence of the American elite.

Interesting Fact: The gardens at Kykuit feature over 100 outdoor sculptures, monuments, and fountains.

3. Enjoy the Hudson River Museum

The Hudson River Museum is located in the city of Yonkers, NY, and is a must-visit site for art lovers and history enthusiasts. The museum houses various art exhibitions, planetarium shows, and a charming object collection from the Hudson River Valley region. There is a $7 admission fee for adults, but the cost is well worth it for the unique experience.

Interesting Fact: The Planetarium at the Hudson River Museum has the only digital dome projector in Westchester County.

4. Stopover at Thunder Ridge Ski Area

Thunder Ridge Ski Area is the perfect destination for anyone looking to engage in outdoor winter sports, located in Patterson, NY. You will find a massive 1000-foot drop, comprising 22 exciting ski trails. Thunder Ridge has five lifts, a terrain park, and an outstanding ski school for those who want to learn the ropes. The site is open year-round for excellent hiking, mountain biking, and zip-lining during warmer weather.

Interesting Fact: Thunder Ridge is situated atop a flat-topped mountain that is 1,200 feet high.

5. Catch a Flick at The Jacob Burns Film Center

The Jacob Burns Film Center is a cultural jewel in the city of Pleasantville, New York. The center's primary focus is on showing indie and foreign films, which promises a unique cinema experience. Besides the modern theatre, movie enthusiasts can enjoy a small café, lounge area, and reading room. Visitors can also take part in special events, such as film festivals, educational programs, and live performances.

Interesting Fact: The original concept for the Jacob Burns Film Center came from Steven Spielberg, who wanted to create a haven for film lovers.

Conclusion

In conclusion, this road trip from Cheshire, Connecticut, to Pleasantville, New York, promises to be an exciting adventure. The scenic route provides spectacular views of the Hudson River Valley, charming towns for pit stops, and plenty of attractions for every taste. It takes around two hours to complete the journey, making it an ideal escape for a day trip or long weekend. With our curated list of top things to do, you're sure to have an unforgettable journey.

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