5+ Remarkable Towns in Westchester: Which is the Best One? (2024)

5+ Remarkable Towns in Westchester: Which is the Best One? (1)

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?

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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.

READ MORE
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).

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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.

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

5+ Remarkable Towns in Westchester: Which is the Best One? (4)

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.

READ MORE
23+ Exciting Things to do in Peekskill, NY

5+ Remarkable Towns in Westchester: Which is the Best One? (5)

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.

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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.

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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.

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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.

5+ Remarkable Towns in Westchester: Which is the Best One? (9)

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

  • wander Main Street in Downtown Yonkers to the waterfront
  • visit and enjoy this ‘Walled Garden’ (use the link to read my article all about Untermyer)
  • spend the afternoon at the Hudson River Museum (use the link to read my article all about Hudson River Museum)
  • shop along Central Avenue, Cross County Shopping Center or Ridge Hill Mall or visit a movie theater to catch a movie.
5+ Remarkable Towns in Westchester: Which is the Best One? (10)

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.

READ MORE
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)

5+ Remarkable Towns in Westchester: Which is the Best One? (11)

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.

5+ Remarkable Towns in Westchester: Which is the Best One? (12)

READ MORE
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.

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

5+ Remarkable Towns in Westchester: Which is the Best One? (13)

Plan Your Next Lower Hudson Valley Outing with Ease!

These Lower Hudson Valley Digital Resources Will:

  1. Give you a Quick & Easy way to research places in the Lower Hudson Valley
  2. Be your Go-To Resource when you run out of ideas for places to go
  3. Help you Save Money while on your outing
  4. Help you Discover Places that may be right in your community & that you may not have thought of

Use coupon code: WELCOME60 for 60% off

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…

5+ Remarkable Towns in Westchester: Which is the Best One? (14)
5+ Remarkable Towns in Westchester: Which is the Best One? (15)

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5+ Remarkable Towns in Westchester: Which is the Best One? (18)

Jackie is the HV blogger behind Hudson Valley Explored, featuring the best things to do, places to see and weekend getaways. Get information from a local who is seeing it all! She lives in the Mid-Hudson Valley Region with her hubby and kids.

5+ Remarkable Towns in Westchester: Which is the Best One? (2024)

FAQs

What is the richest town in Westchester County? ›

Scarsdale and Rye, two of Westchester's toniest towns, are heading a new list of the wealthiest communities across the U.S.

What is the most liberal town in Westchester? ›

Hastings-on-Hudson (Westchester) Dobbs Ferry's hipster neighbor, Hastings-on-Hudson boasts some impressive stats for liberal-leaning families.

What is the oldest town in Westchester? ›

Pelham is the oldest town in Westchester County. Thomas Pell signed a treaty in 1654 with the Siwanoy Indians to buy what is not only the Town of Pelham but is all of the borough of the Bronx and the land along Long Island Sound north to the Rye border and inland to the Bronx river.

What is the most expensive place to live in Westchester? ›

Bronxville

With a median home price of $2,652,477 and a median rent of $3,211, Bronxville is the most expensive city on our list. Based on the growth in home prices in Bronxville over the last 3 years, it ranks No. 1 among all the cities in Westchester County.

What is the poorest town in Westchester County? ›

Some of the highest poverty rates within Westchester County were found in its larger population centers, including Mount Vernon (14%), Yonkers (13%) and New Rochelle (11%).

Which town in Westchester has the lowest property taxes? ›

The city with the lowest all-in property tax rate was Rye, in Westchester County, at $19.20 per $1,000.

What celebrities live in Westchester? ›

Kate and Rooney Mara, Richard Gere, Bea Arthur, Chevy Chase, Michael Douglas, Felicity Huffman, Ralph Lauren, Blake Lively, Ryan Reynolds, Martha Stewart, Rob Thomas, Catherine Zeta-Jones and the late Mary Kennedy all call or have called Bedford home. Yonkers' star-dazzled roster includes Mary J.

What is the biggest town in Westchester County NY? ›

The largest city in the county by population is Yonkers with over 211,000 residents. The city with the highest population density is Mount Vernon with a density of 15,564 individuals per square mile. The towns of Harrison, Mount Kisco, and Scarsdale are coterminous with the village of the same name.

What is considered Upper Westchester? ›

Northern Westchester refers to the upper portion of Westchester County, New York, a suburban area north of New York City. Lying north of Interstate 287/Cross Westchester Expressway, these communities are distinguished by distance from New York City and their more rural character from those of Southern Westchester.

What is the smallest town in Westchester NY? ›

Data for Westchester's smallest city, the City of Rye --- NOTE: The CITY of Rye is not to be confused with the TOWN of Rye or VILLAGE of Rye Brook.

Where did Bruce Willis live in Westchester NY? ›

Bruce Willis is packing up and moving back to the West Coast, leaving behind his massive 22-acre Westchester estate. The “Die Hard” actor's property in Bedford Corners has hit the market for $12.95 million, the Wall Street Journal reported on Thursday.

What is the best school district in Westchester, NY? ›

The Best School Districts in Westchester NY and Hudson Valley based on 4-year graduation rate
  • Scarsdale High School with 99.7%
  • Edgemont High School with 99.3%
  • North Salem High School with 99.1%
  • Byram Hills High School with 99%
  • Pelham Memorial High School with 99%

Where do rich people live in Westchester? ›

Scarsdale. Located in Southern Westchester County, Scarsdale is known for its luxury real estate market and convenient commuter rail service to New York City. It ranks as one of the wealthiest New York City suburbs, with a median household income of around $500,000.

Where is the safest place to live in Westchester County? ›

The Safest Small Municipalities in Westchester are Pleasantville #1, Briarcliff Manor #2, Irvington #3, Bronxville #4, and Croton-on-Hudson #5. The Safest Mid-Size Municipalities in Westchester are Lewisboro #1, Rye #2, North Castle #3, Bedford #4, and Scarsdale #5.

How many billionaires live in Westchester County, NY? ›

Forbes' 35th Annual World's Billionaires List: Facts And Figures 2021, by Kerry Dolan, 10 Billionaires call Westchester County home. Two live in Rye, and one each in Mt. Kisco, Katonah, Scarsdale, Croton on Hudson, Yorktown, Larchmont, Tarrytown and Bedford.

Who is the richest person in Westchester NY? ›

These Are the Richest People From Westchester
  • #1 – Jeff Bezos. Topping the list again this year — and perpetually — is Amazon founder and CEO Jeff Bezos. ...
  • #7 – Mark Zuckerberg. ...
  • #16 – Michael Bloomberg. ...
  • #162 – George Soros. ...
  • #200 – Dr. ...
  • #253 – David Siegel. ...
  • #280 – Ralph Lauren. ...
  • #648 – Daniel Och.
Apr 8, 2020

How many millionaires are in Westchester County, NY? ›

Of 32,810 New York tax filers who earned more than $1 million a year in the latest public records, 13,818 live in Manhattan – or 42% of all the state's millionaires. Another 6,644 live on Long Island and 6,679 live in Westchester or Putnam Counties.

Is Scarsdale the richest town? ›

Key Findings. Scarsdale, New York is the wealthiest U.S. suburb. The average household income is $568,942.

Is Westchester the richest county in NY? ›

Westchester County, NY

North of the Bronx lies Westchester County, the second-wealthiest county in New York.

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