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?

This article contains affiliate links. I make a small commissions for purchases made through links at no extra cost to you.
Read my disclosure for more info.


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.

Essentials you need for any Hudson Valley Outing:

Hudson Valley Directory

Personalized Hudson Valley Directory

Hudson Valley Counties T-Shirt

Personalized Hudson Valley T-shirts

Picture Perfect Adventures in the Hudson Valley Ebook and Planning System

101+ Things to do in the HV for $10 or less

Click below to see items I always have during my Hudson Valley Outings:

  • First Aid Kit: Because ‘you never know’ when an accident happens and you need supplies quickly.
  • Lightweight Poncho: If you’re going to be out all day exploring, you never REALLY know what the weather will be like. You think you do, but, in the Hudson Valley, you really don’t know.
  • Small, Lightweight Tripod: This is my GO-TO Tripod for every single outing I go on. It’s great for taking photos of yourself that are not selfies. This one comes with a bluetooth remote that makes that process easier.
  • Backpack or Cross Body Purse – These are my First Choice when choosing a bag for my Hudson Valley outings.
  • Power Bank for my phone – While out walking all day and taking photos, I use this power bank to make sure that I will not run out of battery on my phone.
  • Comfortable walking shoes – My favorite walking shoes are by Skechers, because they are soft and the memory foam feels great on my feet.

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. 


The Ultimate Hudson Valley Guide

Make sure to 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

Make sure to reference my article all about Things to do in Peekskill, NY for a full list of fun things to do in this popular Hudson River city. 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

Looking for Local Deals?

Take a look at Groupon and see what this week’s deals are.



Hudson Valley Apple Picking Guide

Make sure to reference this Apple Picking Guide: Tips and List Orchards before heading out on any Hudson Valley 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.

Until the Next Adventure…

Signature for Jackie at Hudson Valley Explored


Jacqueline Ramirez

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


Discover More in Westchester County:

Hudson Valley Towns listed on this sign at Esopus park

Best Hudson Valley Towns along the Hudson River

As a Hudson Valley Explorer, I am fascinated by all the Hudson Valley towns and cities. I have an extremely long list of all the Hudson Valley towns & cities I will be visiting in the near future. But what about those Hudson Valley towns and cities by the Hudson River? Are they more special …

Best Hudson Valley Towns along the Hudson River Read More »

Peekskill waterfront and Charles Point.

23+ Exciting Things To Do In Peekskill NY: Westchester County, NY

If you’re wondering about Peekskill, I am here to tell you that Mrs. Garrett and her girls’ school is definitely not there anymore. I know that I am showing my age, but whether you get there by train or by car, there are so many things to do in Peekskill that you will wonder why …

23+ Exciting Things To Do In Peekskill NY: Westchester County, NY Read More »

The dragon from the Great Jack O'Lantern Blaze in Westchester County, NY

The Great Pumpkin Blaze/The Great Jack O’Lantern Blaze: You Won’t Believe Your Eyes

The Great Jack O’Lantern Blaze, in Croton-on-Hudson, NY, is the Tri-State Area’s Biggest Fall Event. Also known as “The Hudson Valley Blaze” or “The Great Pumpkin Blaze”, this event is first-rate and is only found in the Hudson Valley and on Long Island. Would you believe that there are more than 7,000 illuminated jack o’lanterns …

The Great Pumpkin Blaze/The Great Jack O’Lantern Blaze: You Won’t Believe Your Eyes Read More »

Statues at Untermyer Gardens; one of the most beautiful of Yonkers Parks

The Gem of Yonkers Parks: Untermyer Gardens

Step inside the ‘Gleaming Gem’ of Yonkers parks. Out of all the parks and gardens in Yonkers, NY, (and there are many) one particularly stands out from the rest – Untermyer Park. Would you believe it if I told you that the Lower Hudson Valley is home to an array of beautiful Hudson Valley parks …

The Gem of Yonkers Parks: Untermyer Gardens Read More »

The Sculpture garden at Katonah Museum

Westchester Museums: 9+ can’t miss spots

I’m always on a mission to explore more of Westchester County, NY. There is an abundance of Westchester Museums in the area and they are not all about art. Contrary to popular belief, a museum does not have to be boring and only filled with older oil paintings. Many museums are not housed in plain-looking …

Westchester Museums: 9+ can’t miss spots Read More »

Chagall Stained Glass

Chagall Stained Glass & A Matisse Window in Westchester Co.: An Artistic Treasure

Would you think that behind these doors sits works of art so profound that visitors flock from all over to admire them? Union Church of Pocantico Hills looks like a beautiful, modest church from the outside. The Chagall stained glass and Matisse window are what dreams are made of.   Inside Union Church, one can …

Chagall Stained Glass & A Matisse Window in Westchester Co.: An Artistic Treasure Read More »

Stuart's Fruit Farm and Bakery

Stuart’s Fruit Farm: The Oldest Working Farm in Westchester County, NY

Choosing a place to go apple picking in the Hudson Valley can be quite tricky. With so many choices in and around the Hudson Valley, this task can be overwhelming. However, I am here to share our experience going to Stuart’s Fruit Farm in Granite Springs, NY and help you decide if Stuart’s Farm is …

Stuart’s Fruit Farm: The Oldest Working Farm in Westchester County, NY Read More »

Westchester Children's Museum Sign in Rye, NY

Westchester Children’s Museum: Explore, Create, Learn & Play

The Children’s Museum is a quaint space that offers activities for children of all ages.

Hudson River Museum

4 Things I Learned From Visiting the Hudson River Museum

On the banks of the Hudson River in Yonkers sits another gem of a place

Shopping Cart