Things To Do In Westchester County NY: Top 11 Most Unique | Stanton House Inn

lyndhurst castle is one of the best things to do in westchester county, nyWestchester County is usually assumed to just be an area of people who commute into New York City for work. Locals know it is a great area to explore all the fabulous things to do in Westchester, NY.


As close to New York City as Greenwich, Westchester County also makes a perfect short getaway from the hustle and bustle of the city. There are plenty of things to do in Westchester County, NY, for every type of visitor:

  • Rockefeller estates
  • historic colonial homesteads
  • beautiful hiking
  • well-preserved farming towns


Best of all, all these attractions are only a short drive away from the Stanton House Inn in downtown Greenwich, Connecticut. Greenwich is only a short drive or train ride away from:


  • Rye



  • White Plains


  • Harrison


  • Bedford


  • North Castle




In more than a few instances, it’s easier to reach some of the upper Westchester County towns via the train from NYC to Greenwich before getting a taxi north.


View our top picks for the best things to do in Westchester, NY below and plan your getaway to our Connecticut shoreline bed and breakfast.

Top 10 Things to Do in Westchester County, NY

Our 10 must-see things to do in Westchester are:

1. Kykuit

Kykuit: the Rockefeller Estate is situated on the highest point of the Pocantico Hills hamlet. It’s one of the best things to do do in the Hudson Valley. It is also known as the John D. Rockefeller estate after the eponymous oil tycoon and capitalist whose family lived in the house for four generations. Featuring a view of the New York City skyline only 25 miles south, this beautiful estate and home is now open to the public.

2. Rockefeller State Park Preserve

The Rockefeller State Park Preserve is a beautiful state park in Sleepy Hollow, New York. It is perfect for a long walk on wooded hiking trails. With many examples of varied habitats, the National Audubon Society has designated it an “Important Bird Area”.

3. Capitol Theatre

The Capitol Theatre of Port Chester, NY, has recently re-opened as a concert venue. It attracts many major musicians and performers. This historic theater is well-worth a visit for a show, and an easy train ride away from NYC and Stanton House Inn!

4. Ward Pound Ridge Reservation

At 4,315 acres, Ward Pound Ridge Reservation is the largest park in Westchester County, NY. It offers miles of wooded trails, expansive vistas, and endless opportunities for outdoor recreation. The park originally had more than thirty farms within its boundaries but was dedicated as Pound Ridge Reservation in 1938. Today, guests can enjoy everything from camping and fishing to hiking and even cross-country skiing

5. Rye Playland

Located on the shores of the Long Island Sound, Rye Playland in Rye, NY, has been an area staple since 1927. It is even part of the National Register of Historic Places. Also referred to as just Playland, this unique Art-Deco style amusement park sits on 280 acres.  It features:

  • Ice skating rinks
  • An Olympic-size pool
  • Various restaurants and concession stands
  • Thrilling rides – seven of which pre-date 1930

A historic theme park on the water in Rye, New York, Rye Playland is an opportunity to enjoy a time gone by. A boardwalk, beach, and free summer concert series add to the fun experience. Be sure to stop by for fireworks every Friday in July and August!

6. Lyndhurst

Overlooking the Hudson River in Tarrytown, New York, is the majestic Lyndhurst mansion. Now a historic site, Lyndhurst is one of America’s finest Gothic Revival mansions. Rolling lawns are accented with century-old weeping Beech trees and rose gardens. With a fascinating past and old-world elegance, Lyndhurst is a wonderful place to visit during any time of year.

7. White Plains Shopping

Looking for the perfect gift for that special someone or just want to indulge in some retail therapy for yourself? Westchester, New York is the ideal place to get your fix. In particular, the downtown area of White Plains, New York, is the leading retail hub in Westchester County. It offers a variety of shopping districts and malls that are filled with famous New York-based specialty stores. From high-end brands to affordable, quality merchandise, you’ll find it all when you spend a day shopping in White Plains. Make sure you clear some space in the car for all your bags!


the view from the top of bear mountain state park is one of the best westchester county attractions8. Bear Mountain State Park

The park, first opened in 1913 on a site that was once considered as a location for a prison, is home to a variety of terrains, from mountainous climbs to water view paths. Just 45 miles away from New York City, some Manhattan skyscrapers are even visible in the distance. Far from the industrial hubbub, Bear Mountain State Park hiking trails offer a wildlife oasis away from the Big Apple. Whatever path you choose, the panoramic sights are incredible to absorb along some of the best hiking trails in upstate New York.

9. Mianus River Gorge

One of the best things to do in Bedford, New York, the Mianus River Gorge Preserve offers 755 acres of rich woodland and old-growth forest. It’s less than an hour away from the hustle and bustle of New York City (and a 24-minute drive from the Inn). The Preserve provides a habitat for hundreds of species of animals, fungi, and organisms in the soil and water. A walk will expose you to various types of trees, shrubs, vines, herbs, and ferns.

10. Old Croton Aqueduct Trail

hiking is one of the best things to do in westchester county, nyOriginally constructed in 1837, the Old Croton Aqueduct in Dobbs Ferry, New York, is a National Historic Landmark. It attracts thousands of visitors each year. The 41-mile aqueduct runs from Van Cortlandt Park in Bronx County to the Croton Dam in Croton-on-Hudson, NY. And the aqueduct itself is covered by a scenic path known as the Old Croton Aqueduct Trail. Winding through urban centers and small communities, the trail passes numerous historic sites, preserves, and landmarks and offers abundant recreational opportunities during any time of year.


Curious about what else there is to do in Westchester County? Here are a few recent blog articles many of our guests have found useful:

  1. 10 of the Best Colleges in Westchester, NY
  2. 3 of the Best Haunted Houses in Westchester and Nearby
  3. Some of the Apple Orchards that are closest to Greenwich, Connecticut are in Westchester County


Even more unique things to do in Westchester County & the Hudson River Valley

Still looking for something a little unique?


A few more options include:

Van Cortlandt Manor

A visit to the 17th-century Van Cortlandt Manor is a fascinating look into the Hudson River Valley’s colonial history. Take a guided tour to learn about the Van Cortlandt family’s contributions to the development of the property. And come in the fall for the annual Great Jack O’Lantern Blaze at Van Cortlandt Manor, a truly one-of-a-kind experience. Over 7,000 hand-carved, illuminated pumpkins and fall-themed treats are on display at this spectacular event in the town of Croton-on-Hudson, NY.


The Skinny House

The Seely House, a unique 10 foot wide house built in 1932 by Nathan Seely. This oddity in Mamaroneck, New York, is a testament to his dedication to building homes for African-Americans during the Great Migration. After losing everything in the 1929 Stock Market Crash, Nathan’s friend and neighbor offered him a 12 1/2-foot-wide strip of land between the two houses. The house was built using salvaged railroad ties and steel cables, and was added to the National Register of Historic Places in 2015.



What is one of the Best Places to Stay Near Westchester County?

Room 32, king bed in our bed and breakfast near Westchester County, NYBed and breakfasts in Westchester County seem to slowly be disappearing. Luckily, the Stanton House Inn is still close to the Hudson Valley and Westchester County. In fact, our romantic bed and breakfast near NYC is close to so many attractions and activities. We’re accessible by car or train from New York City, as well as much of Westchester County and the attractions on this list.


Be sure to look at our specials and packages before planning your romantic weekend getaways near NYC with us.