The Top Things to Do in Westchester County, New York

Photo of Anne Bauso
20 September 2021

Just north of New York City, Westchester County is one of the oldest inhabited regions in America, rich in history and charm. Visit the storied Rockefeller estate Kykuit, or hike through the leafy trails of FDR State Park while you’re here.

Part of New York’s beautiful Hudson Valley, Westchester offers gorgeous rolling countryside, grand Gilded Age architecture and farm-to-table restaurants. It’s just a 30-minute drive from Manhattan, so you quickly leave the skyscrapers behind for riverside views and peaceful hiking trails. Below are Culture Trip’s recommendations of things to do in Westchester County.

Eat Brooklyn-style pizza in Polpettina

Restaurant, Italian, $$$
closeup of a plate with a pile of eggplant chips
Closeup of a plate with a pile of eggplant chips | © nito / Alamy Stock Photo

With two locations in Westchester, Polpettina specializes in pizza and meatballs that you should go out of your way to try. Inside, you’ll find a cozy, wood-clad interior with an industrial feel. However, with limited seating, it is worth coming by at lunchtime, as it can get very busy during dinner hours. Make sure you try the eggplant chips followed by the beef meatballs soaked in tomato sauce with ricotta and pecorino.

Peruse the Hudson Valley Center for Contemporary Art

For centuries, Hudson Valley has been a source of inspiration for artists, and Hudson Valley Center for Contemporary Art continues that legacy. The objective here is twofold: it’s dedicated to enhancing understanding of contemporary art and its connection to social issues, as well as improving its community of Peekskill, an emerging art and cultural hub in Westchester County. Visit the 12,000sqft (1,115sqm) exhibition space in a former warehouse, and set out on a self-guided tour of the sculpture trail along the river and through the town.

Stroll around Kykuit, the Rockefeller Estate

Kykuit, the Rockefeller Estate | © Felix Lipov/Shutterstock
Experience both natural beauty and history at the awe-inspiring riverfront home of John D Rockefeller and several generations of his ancestors. A National Trust for Historic Preservation site, this family estate includes vast grounds overlooking the Hudson River, a classic car museum, and a spectacular collection of fine and decorative art, featuring such treasures as Pablo Picasso tapestries and Alexander Calder sculptures.

Get lost in Lyndhurst

This magnificent 1838 gothic revival mansion was once owned by Jay Gould, railroad tycoon and robber baron of the Gilded Age. Fans of Dark Shadows might recognise the mansion’s imposing, castle-like presence from the 1970s films, which were largely shot here. The historic structure is complemented by 67 acres (27ha) of immaculately manicured grounds with river views and a rose garden with 500 bushes. The splendid interiors feature maple bowling lanes and a museum-worthy collection of original paintings, furniture, and artefacts including Tiffany lamps.

Marvel at the New Croton Dam

USA, New York State, New Croton Dam
New York State, New Croton Dam | © RooM the Agency / Alamy Stock Photo
The New Croton Dam is a marvel of engineering. Widely thought to be among the largest examples of hand-hewn masonry in the world (along with the Egyptian pyramids and the Great Wall of China), the dam is breathtaking. Rising 300ft (91m) from a 216ft (66m) thick base, it offers gorgeous views of the rushing water. Beyond marvelling at the dam and taking in the scenery, Croton Gorge Park is a prime backdrop for fishing, picnicking, hiking, sledding, or simply relaxing to the sounds of the waterfalls.

Take a walk through FDR State Park

Home of Franklin D. Roosevelt National Historic Site, Hyde Park, NY, USA
Home of Franklin D. Roosevelt National Historic Site, Hyde Park, NY, USA | © dbimages / Alamy Stock Photo
Located 40mi (64km) north of New York, this 960-acre (388ha) park is a truly enormous space – bring a picnic in the summer months or kick through golden leaves in the fall. One of the highlights is a mammoth pool; it’s twice the size of an Olympic one and can hold up to 3,500 bathers. On top of this, there are two soccer pitches, plus a pair of NCAA-regulation basketball courts. If you like spending time by the water, make your way to Mohansic Lake and Crom Pond for boating and fishing.

Swing by Ruby's Oyster Bar & Bistro

Bar, Bistro, Restaurant, Seafood, French, $$$
Tray of fresh oysters in shells, Whitstable, Kent, England, United Kingdom
Tray of fresh oysters in shells | © Greg Balfour Evans / Alamy Stock Photo
Serving fresh seafood with a French twist, Ruby’s Oyster Bar in Rye is one of the best restaurants in the area. Come for the poke tuna tartare, a customer favorite, or go all-out with the Triple Tier – a veritable feast of lobster, oysters, shrimp, ceviche and clams. Make sure to call in a reservation well in advance, this restaurant is a popular destination, especially for dinner and weekend brunch.

Grab a coffee from Slave to the Grind

Bar, Cafe, American
Fresh coffee served for breakfast
Fresh coffee served for breakfast | © BlueOrangeStudio / Alamy Stock Photo
Looking for more than just a cup of coffee? Slave to the Grind can take care of that. Established in 1993, this cafe offers eight different brewed coffees, along with their original coffee beans for sale. The breakfast treats, desserts and sandwiches are all extremely popular at this eclectic coffee joint. In the back, there’s a beautiful mahogany bar, salvaged from a hotel that burned down in Bronxville. Its great ambiance and friendly employees make Slave to the Grind a must-visit.

Still got time to burn in New York? Read our guide to the best things to do in NYC. When you’re done for the day, indulge in some more of the state’s culinary specialities, then find your resting point at one of its many places to stay, bookable through Culture Trip.

Henry Lilly contributed additional reporting to this article.

These recommendations were updated on September 20, 2021 to keep your travel plans fresh.

Cookies Policy

We and our partners use cookies to better understand your needs, improve performance and provide you with personalised content and advertisements. To allow us to provide a better and more tailored experience please click "OK"