Escape to Westchester County for a Weekend of Historical Charm, Food and More

by Tom Lavecchia

Westchester County, nestled just north of New York City, often gets overlooked in favor of its more famous southern neighbor. Yet, those who venture into this scenic area will find a treasure trove of activities, rich history, and picturesque towns that promise a delightful escape from the daily grind. Over a recent weekend, we explored a few gems in Westchester that exemplify the unique allure of this region.

Sleepy Hollow: A Walk through Legend and Beauty

Our journey began in Sleepy Hollow, a village synonymous with Washington Irving’s legendary tale, “The Legend of Sleepy Hollow.” Stepping into this historic village feels like walking into the pages of the story, surrounded by the lush landscapes that inspired Irving’s famous Headless Horseman.

A visit to Sleepy Hollow isn’t complete without a tour of the Sleepy Hollow Cemetery, where Washington Irving himself is laid to rest. The cemetery, sprawling and serene, offers guided tours that delve into the history of the area and its most famous residents. We wandered among ancient tombstones, enveloped by the whispering trees, and felt a connection to the past that is palpable.

For families, Philipsburg Manor is a must-visit. This restored 17th-century milling and trading complex gives a glimpse into the lives of the Dutch settlers and the enslaved Africans who lived and worked there. The manor house, with its period artifacts and interactive tours, paints a vivid picture of colonial life.

Tarrytown: A Blend of Shopping and History

Just a stone’s throw from Sleepy Hollow is Tarrytown, a vibrant village that offers an eclectic shopping experience. Main Street in Tarrytown is lined with quaint boutiques, antique shops, and local eateries that reflect the diverse character of the area. We spent hours meandering through the shops, each offering unique finds—from vintage clothing and rare books to artisanal chocolates and handmade jewelry.

A highlight of our Tarrytown excursion was a visit to Lyndhurst, one of America’s finest Gothic Revival mansions. The estate, overlooking the Hudson River, offers guided tours that showcase its stunning architecture, art, and antiques. The grounds, with their rolling lawns and ancient trees, offer a peaceful retreat and panoramic views of the river.

Playland Park: Thrills and Learning for Kids

With our spirit of adventure still alive, we headed to Playland Park in Rye. This historic amusement park, opened in 1928, is a mix of nostalgic rides and modern attractions, providing fun for all ages. The famous Dragon Coaster, a wooden roller coaster that has been thrilling visitors since the park’s early days, was a definite thrill.

Adjacent to the amusement rides, the Playland Kid Museum offers interactive exhibits that engage children in learning through play. The museum focuses on the themes of science, art, and music, making it an educational as well as a fun visit for the younger ones.

Comfort and Convenience at Courtyard by Marriott

After a full day of exploration, we found solace at the Courtyard by Marriott in Tarrytown. The hotel provided a perfect blend of comfort and convenience, with modern amenities that cater to both leisure and business travelers. The rooms were spacious and well-appointed, ensuring a restful night’s sleep.

The hotel’s location also made it ideal for exploring the surrounding area. Positioned close to major highways and with easy access to public transportation, it was a breeze to navigate our way around Westchester.

Culinary Delights of Westchester

Westchester’s culinary scene deserves a special mention. In Tarrytown alone, we experienced a diverse palette of flavors. From cozy cafes serving farm-to-table breakfasts to upscale restaurants offering gourmet dinners, the food scene was a delight. The Twisted Oak, a local favorite, stood out with its innovative American cuisine, focusing on locally sourced ingredients and a seasonal menu that captivates the taste buds.

Westchester County proved to be a destination filled with unexpected surprises and delights. From the haunting beauty of Sleepy Hollow to the charming streets of Tarrytown, the historical mansions, and the thrill of Playland, there was never a dull moment. Staying at the Courtyard by Marriott in Tarrytown provided the perfect home base from which to explore the rich tapestry of experiences that this unique area of New York offers.

As we returned to New Jersey, we brought back not just souvenirs, but also a collection of memorable experiences and stories to share. Westchester County, with its blend of history, culture, and entertainment, is a weekend getaway that truly offers something for everyone. Whether you’re a history buff, a shopping enthusiast, a family with kids, or just looking to relax and unwind, Westchester welcomes you with open arms and countless adventures.  

Looking to make a visit? Plan your trip here to Westchester here

About the Author/s

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Tom is a lifelong New Jersey resident, Rutgers and FDU alumni and the publisher of The Digest.

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