List of Towns in Westchester: Which is the Best One?

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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Towns

Tips for 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 does not 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.

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?

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

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

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

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.

Sleepy Hollow

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.

Hudson Valley Fall Events Not to be missed

Since October is the best time to visit Sleepy Hollow, check out this article listing great events happening in the Fall throughout the Hudson Valley.

Tarrytown

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

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

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, NY

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

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, this amazing event is very popular in the Hudson Valley and usually sells out.

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.

Some towns in Westchester are perfect to visit during apple picking season.
Stuart’s Farm & Orchards, Granite Springs, NY

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.

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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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Take some time to discover all the things to do in Westchester County NY. This area is so close to New York that it's the perfect day trip from New York City. Full of Hudson Valley Art & Culture, Westchester County NY is the great for Hudson Valley Families.

Jackie from Hudson Valley Exposed

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I am a Native New Yorker who moved to the Hudson Valley for college and instantly fell in love. I believe that you don’t have to travel far in order to have an Amazing Adventure. Let me Expose you to your Next HV Adventure and teach you how to make memories the will last a lifetime.