Never miss a story
Menu & Search
A Weekend Guide to Tarrytown & Sleepy Hollow, NY

A Weekend Guide to Tarrytown & Sleepy Hollow, NY

This summer, for the second summer in a row, I’ll be living in New York City. I have had such a wonderful time acquainting myself with the city over the past year, and now that I know my way around a little better, one of my goals is to take short trips around the region. Tarrytown, NY, a historic village along the lower Hudson River Valley, named one of America’s prettiest towns by Forbes, was high on my summer list.

This Memorial Day weekend, Rolan and I spent a wonderful day with his relatives in Rye, NY, swimming, sea kayaking, paddle boarding, and generally trying to keep up with his little cousins. When our sunny, seaside day was done, we took the quick drive over to Tarrytown.

While we made Tarrytown an overnight trip, it is an easy day trip from NYC, about 40 minutes by car and a little over an hour taking public transit and the Metro-North Railroad. Because many of the points of interest are spaced far apart, it’s definitely a plus to come with your own wheels. If you do take the Metro-North, make sure to check for package discounts on train tickets and tours of the area’s historic sites.

For our trip, we stayed at the Tarrytown House Estate, a lush and expansive property featuring a 19th-century stone mansion, meticulous landscaping, a toasty fire pit, Adirondack chairs overlooking the outdoor pool, and quiet, comfortable rooms. We found excellent discounted rates for our stay on Hotel Tonight, an app I highly recommend for spontaneous adventures.

We started our day with hefty Greek sandwiches at Lefteris Gyro along Tarrytown’s charming Main Street. Enjoying the sun and warmth that coincided so perfectly with the weekend, we meandered among the small shops and picked up some ice cream at Main Street Sweets.


From Main Street, we hopped over to Lyndhurst, a castle-like mansion most famously owned by Jay Gould, a Gilded Age businessman who, in his day, was the richest man in the world and, by some accounts, “the most hated man in America.” Lyndhurst was a literal escape for Gould, as it was not only a gorgeous property but also a place where Gould could protect himself against the many people who wanted to kill him.


While you can stroll Lyndhurst’s verdant grounds for $5, if you want to see the inside of the mansion, you have to buy tickets to a scheduled tour, which we did and thoroughly enjoyed ($16 for adults plus $2 service fee per ticket if you reserve online). Originally constructed in 1838 and later expanded upon, Lyndhurst has a rich history. Unlike most historical homes I have toured, the large majority of Lyndhurst’s contents are original to the families who lived there. The mansion is full to the brim with custom furniture, Tiffany stained glass, and intricate trompe l’oeil surfaces painted to look like marble, rosewood, and leather, all of which make the tour well worth it.


My favorite part of the house is the chapel-like art gallery, defined by a massive Tiffany window, gorgeous gallery walls, and a small loft for musicians to play in above gathered guests.

Across from the art gallery, the mistress of the house would wake up each morning in the most lavish bed, covered in colorful light.

When we finished our tour, we had a wonderful time contentedly lying in the grass and walking under the dappled light of the abundant trees. The air on the property was such a botanically refreshing respite from New York City, and the rose gardens in full bloom only added to its perfume.



After filling up on roses, we drove over to Philipsburg Manor in the adjacent town of Sleepy Hollow, NY. We shared some snacks from the Manor café while strolling along the Manor’s working gristmill. While we ran out of time on this trip, we someday hope to visit Kykuit, a sprawling Rockefeller estate (accessible exclusively through scheduled tours that depart from Philipsburg Manor).

Having soaked up plenty of history, and faced with most attractions’ shuttering up for the evening, we spent a couple of hours enjoying the Hudson River itself. We walked along the river in Tarrytown’s Pierson Park, drove across the massive Tappan Zee Bridge to the Hudson’s West bank, and sat among picnickers at Nyack Beach State Park before getting some dinner at Red Hat on the River and driving back to Manhattan as the sun set.

I’m so looking forward to this summer, which I’m sure will be a full one, and I can’t wait to keep exploring the Hudson Valley for its bike paths, mountainous hikes, art museums, farms, and wineries. There is so much to see in the area that I frequently find myself lost in a whirlpool of researching, so if you have any favorite spots, please let me know!


  1. 4 years ago

    I love your blog and I’m so glad I discovered it! Also a college student in the Boston area interning in NYC. 🙂 I’m from this area–Bear Mountain and Turkey Mountain are fun hikes, and Stone Barns is a cool farm with good food!

    Let me know if you ever want to collab! 🙂
    Instagram: @funsizedcupcakes

    • Aurelia
      4 years ago

      Hi there, M! Thank you so much for your sweet words and for your tips. I’ve been really wanting to go on a hike, so hopefully I can get out to one of the places you recommended sometime soon! Your blog is lovely, and your bucket list is amazing (so much already accomplished!). Please feel free to email me at [email protected] with any collab ideas you have. I’d love to keep in touch 🙂

      • 4 years ago

        Thanks, Aurelia, you’re so sweet! I’d love to connect – I’ll send you an email. Have fun hiking!! 🙂