5+ Remarkable Towns in Westchester:
Did your favorite make the list?

Westchester County New York is the closest county to New York City. With its richness in history and culture, this makes it a great place to explore in the Hudson Valley, but with so many towns in Westchester, which is the best one to explore?

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Things to know before Exploring Towns in Westchester:

  • Westchester County towns and cities are very different from one another and each may not have the same businesses
  • Many Cities & Towns in Westchester can be reached with public transportation
  • Traffic is often heavy on the Cross County Parkway around the Cross County Mall and on the Hutchinson River Parkway around the vicinity of Mount Vernon.
  • Westchester County has many popular cities that add to the population and makes this one of the densest counties in the area.

All About the Best Towns in Westchester County:

What’s the first thing thing that comes to mind when you think of Westchester County and towns within Westchester?

I think about:

  • Shopping on Central Avenue in Yonkers
  • Going to college in Purchase
  • Visiting the Westchester Mall in White Plains
  • Summer days & night having fun at Playland Park in Rye
  • Riding my bike during Bronx River Parkway Bicycle Sundays

With the diversity of culture, food, and scenery, towns in Westchester can be very different from one another.

Some towns in Westchester boasts Hudson River views, while others do not.

Where is Westchester County New York?

Westchester County NY Map

Located approximately 30 miles North of New York City, with nearly 1 million people living in the county, there’s a diversity of not only people but also things to do and see. Its the first suburban area of its scale where young families and young professionals look to escape city life and live the suburban lifestyle.

Westchester County is located in the southeastern part of New York state, just north of New York City. The county’s borders are the Hudson River to the west, Connecticut’s Fairfield County to the east, Putnam County to the north, and the Bronx and New York City to the south.

Westchester County is home to many suburban communities within its 450 square miles and is known for its affluent towns and villages, historic sites and landmarks, and beautiful natural landscapes.

Due to its proximity to Fairfield County, Connecticut, which is just across the state line, Westchester County is a short commute from many popular destinations in Connecticut, including the city of Stamford, the beaches of Long Island Sound, and the rolling hills of Litchfield County.

Where is the Hudson Valley NY Actually Located?

Map of Westchester County

How can you get to some towns in Westchester County

Westchester County is accessible by:

  • train (Metro-North Railroad)
  • car
  • bus (Bee-line bus service).

Whichever way you get there, make sure you plan ahead and fill the day with fun things to do.

According to Westchestergov.com

“[Westchester County] has retained much of its rural character while adopting the urban and suburban lifestyles dictated by its proximity to New York City.”

Cities & Towns in Westchester: Highlights of things to do

There is something there for everybody interested in visiting the 6 cities, as well as, 19 towns and 23 villages.  Boasting some of the richest towns in New York State, it is no wonder that these major cities and towns in Westchester receive many visitors each and every year.

With its mixture of urban and city life, Westchester County New York is full of places to see and visit. Featuring busy cities and cute towns, people enjoy visiting and exploring towns in Westchester, rich in history, art and culture.
These cities and towns in Westchester County include:

  • Ardsley
  • Bedford Hills
  • Briarcliff Manor
  • Bronxville
  • Buchanan
  • Cortlandt
  • Croton-on-Hudson
  • Dobbs Ferry
  • Eastchester
  • Elmsford
  • Greenburgh
  • Harrison
  • Hastings-on-Hudson
  • Irvington
  • Katonah
  • Larchmont
  • Lewisboro
  • Mamroneck
  • Mount Kisco
  • Mount Pleasant
  • Mount Vernon
  • New Castle
  • New Rochelle
  • North Castle
  • North Salem
  • Ossining
  • Peekskill
  • Pelham
  • Pelham Manor
  • Pleasantville
  • Port Chester
  • Pound Ridge
  • Rye
  • Rye Brook
  • Scarsdale
  • Sleepy Hollow
  • Somers
  • Tarrytown
  • Tuckahoe
  • White Plains
  • Yonkers
  • Yorktown

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Here are some highlights of towns in Westchester and what to do there:

Irvington NY

Located just north of Sleepy Hollow, Irvington

One of the most interesting things to see in Irvington would be the Armour-Stiner (Octagon) House. This hidden gem is not known by many and is a very unique residence. Built in the 1800’s, it is rumored to house a resident ghost. It continues to be a private residence and is only visited by scheduled tour (limit offerings during the Fall of 2020).

The Armour-Stiner House Courtesy of Wikipedia

Katonah NY

There are no shortage of things to see and do in Katonah, NY, as it is home to:

This quaint little village is also full of little shops and eateries sure to fill out anyone’s day.

10+ Inspiring Things to do in and around Katonah this weekend

Visitors to Katonah Museum of Art

Peekskill NY

Peekskill is another Hudson Riverside location that boasts charm and character like no other. Accessible by the Metro-North train, Peekskill is popular with those looking for a day trip from New York City.

The Hudson Valley Museum of Contemporary Art is the highlight of any visit to Peekskill. Peekskill’s Scenic Hudson Park is a connection of beautiful parks, perfect for a walk and take in the scenery. It’s about a mile long and begins at the train station and ends at Fleischmann’s Park.

23+ Exciting Things to do in Peekskill, NY

The sidewalk and shop in Peekskill NY

Sleepy Hollow NY

This famous town is known for everything Halloween.

When you visit the website: Visitsleepyhollow.com you can learn all about the story of Washington Irving and what inspired him to write “The Legend of Sleepy Hollow”.

More activities to do in Sleepy Hollow include taking a self-guided tour of the Sleepy Hollow Cemetery (the resting place of Andrew Carnegie, Washington Irving and others significant to American History), visit Philipsburg Manor, and Sleepy Hollow Lighthouse.

Sleepy Hollow is one of the most important towns in Westchester when it comes to literature. With amazing views of the Hudson River, Sleepy Hollow, NY is one of those picturesque towns that appears only in books.

Sleepy Hollow is also home to Kykuit, the Rockefeller Estate. Home to four generations of the Rockefeller family, this glorious home sits on a majestic hilltop.

Sleepy Hollow Lighthouse is one of the things you can see in one of the most popular towns in Westchester.
Sleepy Hollow Lighthouse

Tarrytown NY

Just south of Sleepy Hollow, sits Tarrytown in central Westchester County. Another Hudson River small town boasting in history and legendary landscapes.

A must-see when in Tarrytown is Lyndhurst Mansion. Today, it is open to the public as a historic site and is listed on the National Register of Historic Places.

This Gothic Revival mansion dates back to the 1800’s and is incredible that it stands so glorious along the Hudson River Landscape. The grounds are accessed through the main gate and the acres of parkland are both inviting & exciting.

The mansion is known for its stunning architecture, including its impressive turrets, elaborate moldings, and stained-glass windows. The interior features original furnishings and decorative arts, including a large collection of Tiffany stained glass.

Visitors can take guided tours of the mansion to learn about its history and the lives of its former owners.

Lyndhurst Mansion is located in Tarrytown, NY. Just one of the towns in Westchester located along the Hudson River.
Lyndhurst Mansion, Tarrytown, NY

Tarrytown and other nearby towns are home to amazing green spaces where you can find the weekly TaSH Farmers Market, in addition to, coffee shops, restaurants and antique shops. This small town is the perfect place to spend the day away from the city. With easy access to the train that takes you directly to Grand Central Terminal, there is no reason why a visit is not in your future.

White Plains NY

Known for it’s shopping, at the Galleria Mall, the Westchester Mall, City Center & Mamaroneck Avenue, there is so much more to White Plains.

The inside of the Westchester Mall, not in one of the town in Westchester, but actually in its largest city

As the largest city in Westchester County, White Plains is home to the Westchester County Center, this venue offers the opportunity to participate in trade shows, and view sporting events & entertainment. In addition, the White Plains Performing Arts Center showcases events and concerts.

Although the city is full of buildings, White Plains also has many open green spaces ready for visitors.
These include:

Yonkers NY

Closest to the New York City border, Yonkers is another one of the towns in Westchester that runs along the Hudson River, Saw Mill River and the Bronx River.

Hudson River Museum in Westchester County, NY is a great place for adults and children alike. It houses a Planetarium and is also connected to Glenview. Yonkers is one of the most popular towns in Westchester.
Hudson River Museum, Yonkers, NY

You can’t go wrong with a visit to Yonkers where you can:

Untermyer Gardens is located in Yonkers, NY - one of the most popular towns in Westchester.
Untermyer Gardens, Yonkers, NY

More Things to See & Do in Westchester County New York:

Bicycle Sundays

Ride your bike along the Bronx River Parkway from Yonkers to White Plains on Sundays during the months of May, June and September from 10 am – 2 pm. It is a great time to ride your bike on the highway without having to share the road with cars.

FREE things to do in Westchester County with or without children.

The Great Jack O’Lantern Blaze

This yearly event takes place from September through November and is the highlight of the Halloween season. Taking place at Van Cortlandt Manor, in Croton-on-Hudson, The Great Jack O’Lantern Blaze is very popular in the Hudson Valley and usually sells out. (use the link to read my article all about The Great Jack O’Lantern Blaze)

The Great Jack O'Lantern Blaze takes place every year in one of the river towns in Westchester.
A display at the Great Jack O’Lantern Blaze

Apple Picking Season

Westchester County is home to some great farms ready for visiting most of the year. Pick your own fruit at several farms and Orchards located in the county, like the Historic Stuart’s Farm in Granite Springs, Outhouse Orchards in North Salem, and Wilkens Fruit and Fir in Yorktown Heights.

Stuarts Fruit Farm is one of the best places to go apple picking in the Hudson Valley

Hudson Valley Apple Picking Guide: Tips and List Orchards

More information about towns in Westchester County:

Westchester County in New York is a great place to live and raise a family in the state of New York, with a wealth of amenities and attractions for residents of all ages. The county is home to many excellent school districts, with good schools at all levels from elementary school to high school.

Families looking to move to Westchester County will find a wide range of real estate listings to choose from, including spacious homes in charming neighborhoods and luxury properties with stunning views of the Hudson River.

While the cost of living in Westchester County can be high, residents enjoy a high quality of life and many benefits, including access to great schools and amenities.

The beauty of Lasdon Park and Arboretum and why it’s a local favorite

50+ Things to do in the Lower Hudson Valley New York Ebook

Plan Your Next Lower Hudson Valley Outing with Ease!

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A Few Things to Know Before Visiting & Exploring Towns in Westchester:

  • Many places listed here are open seasonally. Check each individual location for days/times they are open to the public.
  • Some places charge an entrance, admission and/or tour fee. Check each individual location for more detailed information regarding prices.

Until the Next Adventure…

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