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 Mt. 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 Galleria Mall & the Westchester Mall in White Plains
  • Summer days & night having fun at Playland Park in Rye

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?


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.

There is something there for everybody interested in visiting the 6 cities, as well as, 19 towns and 23 villages. 

Hudson Valley Guide

Reference this Ultimate Hudson Valley Guide for all things having to do with Westchester County. In addition to information about Westchester County New York, I also include practical tips to make your visit successful.


Map of Westchester County



How can you get to some towns in Westchester County?


Westchester County is accessible by:

  • train (Metro North)
  • 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


With its mixture of urban and city life, Westchester County New York is full of places to see.

  • Ardsley
  • Bedford
  • 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

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).

Katonah NY

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

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

Peekskill NY

Peekskill is another Hudson Riverside location that boasts charm and character like no other. Accessible by the MetroNorth 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 great place for a walk and take in the scenery. It’s about a mile long ad begins at the train station and ends at Fleischmann’s Park.

23+ Exciting Things to do in Peekskill, NY

Reference my article all about things to do in Peekskill, NY for a full list of fun things to do in this popular Hudson Valley River Town. Read this article before making any plans to visit 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 Washington Irving’s story 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, visit Philisburg 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. Another Hudson River town boasts history and legendary landscapes.

A must-see when in Tarrytown is Lyndhurst Mansion. 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 sprawling grounds are both inviting & exciting.

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

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.

Home to the Westchester County Center, this venue offers the opportunity to participate in trade shows, and view sporting events & entertainment (cancelled for 2020). In addition, the White Plains Performing Arts Center showcases events and concerts (suspended for 2020).

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

  • Silver Lake Preserve
  • Cranberry Lake Preserve
  • Saxon Woods Park

Yonkers NY

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

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.

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

Hudson Valley Apple Picking Guide

Reference this Apple Picking Guide: Tips & List of Orchards before heading out on any Hudson Valley Fall Apple Picking Outing. I include practical tips and a full list of Hudson Valley apple orchards, as well as, the ability to download the list.

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.

Where to Next???

Now that you have learned about towns in Westchester, let’s see where you should go next…

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Until the Next Adventure…

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Jacqueline Ramirez

Jackie is one of the top bloggers in the Hudson Valley. A solo entrepreneur, she has been featured (along with some of her photos) in several publications, locally and nationwide. Read Jackie’s crazy story, “From a Naive NYC Girl to Popular Hudson Valley Blogger & Author“. Feel free to send Jackie a message here.

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