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Discover Westchester’s Top Towns — And What Makes Them So Unique

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Hartsdale
Photo by Ken Gabrielsen

Whether you dream of rustic grandeur or Main Street USA, you’ll find it within the 450 square miles that make Westchester unlike anywhere else.

Click here to view Our Towns: By The Numbers

Whether you dream of rustic grandeur or classic Main Street USA, the excitement of a vibrant urban hub or a tree-lined suburban neighborhood teeming with civic pride, you’ll find it in real-time plentitude within the 450 eclectic square miles that make Westchester unlike anywhere else in the country.

– Cities –

Mount Vernon

A hub of transit-oriented development (TOD) in the County, Mount Vernon offers its 70,000 residents a variety of neighborhoods, from vibrantly urban areas to traditional suburban enclaves. Just a quick commute to Manhattan via Metro-North, the city is known for both its diversity and its value. With a burgeoning arts scene, Mount Vernon for years hosted such events as The Arts on Third Festival, one of the largest arts-and-entertainment festivals in the county.

New Rochelle

Another TOD hotspot, the “Queen City of the Sound” sits along miles of Long Island Sound shoreline. The city comprises a richly diverse mosaic of neighborhoods: modest apartments, wealthy estates on private islands, older homes on quiet suburban streets, and urban skyscrapers. Home to both Iona College and Monroe College, New Rochelle features such historical sites as the Execution Rocks Lighthouse and Leland Castle, as well as such leisure destinations as the 105-acre Glen Island Park and New Roc City entertainment complex.

Peekskill. Photo by Adam Sommer

Peekskill

Offering an artsy, bohemian vibe and striking river views, Peekskill has become an increasingly sought-after, yet affordable, place to live. This once industrial city’s thriving art-and-culture scene is the byproduct of a visionary early-1990s city-planning strategy to turn unused downtown properties into live/work artist space. Peekskill is also home to such trendy eateries as Fin & Brew, Gleason’s, RameNesque, and the highly anticpated Apropos, on the idyllic grounds of the brand-new Abbey Inn & Spa. Cultural and leisure assets include Hudson Valley MOCA, Paramount Hudson Valley Theater and the 40,000 sq. ft. Spins Hudson, the largest entertainment venue on the river.

Rye

While it’s Westchester’s smallest city, Rye may well be its most sophisticated, with stylish shopping and dining options. Steeped in history, this Sound Shore town was established in 1660 and is the birthplace of founding father John Jay, as well as First Lady Barbara Bush. The home of the Westchester Children’s Museum, Rye is also a mecca of summertime fun, including the historic, art-deco Playland amusement park, an old-fashioned boardwalk, Rye Beach, and Oakland Beach.

White Plains. Photo courtesy of AdobeStock

White Plains

A bustling commercial center and seat of county government, White Plains has attracted the U.S. headquarters of such global corporate giants as Heineken and Danone. A shopper’s paradise, it boasts a free-standing Bloomingdale’s and three major malls: the upscale Westchester, The Galleria and City Center. By night, a varied nightlife scene emerges with myriad bars, pubs, and lounges. Foodies are drawn to the wide array of dining options to be found along Main Street and Mamaroneck Avenue, including Vietnamese, Peruvian, Japanese, classic Southern dining and barbecue, as well the world-class BLT Steak at the sumptuous Ritz-Carlton New York, Westchester.

Aerial view of Yonkers. AdobeStock/Jin

Yonkers

Given its size and proximity to New York City, Yonkers is often referred to “The Sixth Borough.” Blossoming with ongoing riverfront and transit-oriented development, Yonkers is New York State’s fourth-most-populous city. Offering unique entertainment options, residents and visitors can enjoy harness racing, and a full-service casino with 5,300 slot machines. Yonkers is also home of the Hudson River Museum and planetarium, the historic Glenview Mansion Museum, and the spectacular Untermyer Gardens Conservancy. Drink and dine at the city’s abundant bars and restaurants, like the eponymous Yonkers Brewery and Chef Peter Kelly’s X2O Xaviars on the Hudson, where fine food is enhanced by views of both the George Washington and Mario Cuomo bridges.

– Towns –

Bedford

Celebrities like Ryan Reynolds, Blake Lively, Martha Stewart, Bruce Willis, and Ralph Lauren are all residents of this chic town, replete with horse farms and rustic, pastoral beauty. Consisting of three hamlets — Bedford Village, Bedford Hills, and Katonah — the town offers the peace and quiet of a country life, as well cultural treasures like The Caramoor Center for Music and the Arts, Katonah Museum of Art, and the Bedford Playhouse, featuring appearances by the likes of Kerry Kennedy, Glenn Close, Paul Schrader, and Lesley Stahl.

Cortlandt

Divided into two villages — Croton-on-Hudson and Buchanan — and multiple hamlets, including Montrose, Krugers, and Verplanck, Cortlandt is shaped by its many wooded hills, streams and wetlands. Sitting partially along the Hudson River, Cortlandt is located just south of Putnam County. Local residents rely on The Cortlandt Town Center for their shopping needs, complete with big-name clothing stores, movie theaters and its own Walmart.

Eastchester

Comprising the villages of Bronxville and Tuckahoe, Eastchester is an educational hub with award-winning public-school districts, as well as Sarah Lawrence College, both located in Bronxville. Local residents enjoy shopping at Lord & Taylor, Brooks Brothers and Trader Joe’s, dining at the French Riviera inspired Fig and Olive, and browsing the books at Barnes & Noble’s recently renovated store and restaurant complex.

Greenburgh

With more than 90,000 residents, Greenburgh is eclipsed only by Yonkers in terms of population. Measuring 36 square miles, the town incorporates six villages: Ardsley, Dobbs Ferry, Elmsford, Hastings-on-Hudson, Irvington, and Tarrytown, as well as three hamlets — Fairview, Hartsdale, and Edgemont. The Greenburgh Nature Center offers diverse programming for families, while The Greenburgh Public Library in Elmsford offers one of the biggest selections in the Westchester Public Library system. Local foodies enjoy a direct pipeline to farm-fresh produce at Westchester Greenhouse & Farm. Hartsdale’s Poet’s Corner is a charming, traditional suburban neighborhood with single-family homes on streets named for celebrated poets, such as Keats and Longfellow.

Harrison

The town’s hamlet of Purchase is home to the U.S. corporate headquarters of two Fortune 500 giants: MasterCard and PepsiCo. Purchase is the site of two college campuses — Manhattanville and Purchase College, which shares a campus with Boundless Adventures, a new outdoor-climbing and zipline adventure park. Harrison also boasts the first Wegman’s grocery store in Westchester County.

Lewisboro

Rural Lewisboro borders Western Connecticut, touching over the hamlets of Cross River, Goldens Bridge, South Salem, Vista, and Waccabuc. Known for its scenic charm, horse farms, and riding trails, the town is rich with natural parks and preserves, such as Mountain Lakes Camp, with forest trails and ponds, and Onatru Farm Park, with tennis facilities, trails, and playing fields. At 4,700 acres, Ward Pound Ridge Reservation is Westchester County’s largest park, part of which sits in Cross River.  

Mamaroneck

Mamaroneck comprises two villages: tony, upscale Larchmont and the eponymous Mamaroneck, which is frequently recognized as a top place to live in New York State. The village of Mamaroneck is characterized by a lively downtown with Italian, Turkish, French, and Pan-Asian restaurants, along with vintage and antiques shops. Orienta, one of Westchester’s most affluent areas since the late 19th century, was once known as “Hollywood East,” as it was a key center for the film industry of the early 20th century.

Mount Kisco

Nicely ensconced in North Central Westchester, Mount Kisco is packed with a variety of shopping and dining options. Shoppers can enjoy big-box department stores, like Target, Gap, and Kohl’s, along with local standouts like The Elephant’s Trunk. Mount Kisco also features one Westchester’s most varied arrays of cuisine options, including Greek, Indian, Italian, Mexican, Georgian, and Ethiopian, and is the site of the trendy Exit 4 Food Hall, right on Main St. Wellness junkies will enjoy another of Mount Kisco’s unique claims to fame: Westchester’s first and only sensory-deprivation float center, Rise Above Flotation.

Mount Pleasant

With a total area of more than 24 square miles, Mount Pleasant encompasses the villages of Pleasantville and Sleepy Hollow, plus the eastern portion of Briarcliff Manor. Its several hamlets include Hawthorne, Pocantico Hills, Thornwood, and Valhalla. Visit Stone Barns Center for Food and Agriculture in Pocantico Hills to enjoy one of the world’s top-rated restaurants or picnic at the plaza located in front of the Kensico Dam in Valhalla.

New Castle

Comprising the affluent hamlets of Chappaqua and Millwood, New Castle is well-known for its top schools, convenient location, and celebrity residents, including Bill and Hillary Clinton, Ben Stiller, and Vanessa Williams. With a pleasant and walkable downtown, Chappaqua benefits from a recently renovated Metro-North station and a newly completed infrastructure-improvement project. Pay a visit to the Chappaqua Performing Arts Center and check out the local food mainstays, like Lange’s Little Store & Delicatessen and Susan Lawrence Gourmet Foods.

North Castle

A cohesive blend of rural and suburban living, homes within North Castle’s hamlet of Armonk sit on large plots of land, and the small village bustles with excellent eats, high-end boutiques, and lots of well-heeled residents. The town also includes the hamlets of Banksville and North White Plains. Visit Wampus Pond for scenic walks year-round and ice skating come the cold weather. In September, check out the Armonk Outdoor Art Show, a gathering of nearly 200 local artists at the IBM world headquarters.

North Salem

This quiet rural town is said to have more horses than people. Driving through, you’ll spot several farms and open fields where horses and cattle graze. In the fall, apple picking at Outhouse Orchards and fresh-baked goods and produce at Harvest Moon Farm & Orchard won’t disappoint. Get a table at former Best of Westchester winner One Twenty One for a top-notch dining experience.

Ossining Boathouse. Photo courtesy of AdobeStock

Ossining

Home to the storied the Sing Sing correctional facility since 1826, this bourgeoning Rivertown contains two villages: the village of Ossining and a section of Briarcliff Manor. Ossining’s Hudson River waterfront has several marinas and three boat clubs. On a clear day, from the Ossining waterfront, the Manhattan skyline is visible on the horizon. Ossining has an award-winning school district and a rapidly evolving downtown with substantial waterfront development. Also notable is Teatown Lake Reservation, a 1,000-acre reserve with 15 miles of hiking trails, as well as a wildflower sanctuary.

Pelham

The result of a 1654 treaty with Siwanoy Indians, Pelham is the oldest town in Westchester County. The town’s Picture House, a renovated 1920s theater showing arts and indie films, hosts The Film Club with critic Marshall Fine and special screenings with big-name actors, like Ryan Reynolds and George Clooney.

Pound Ridge

Within its scenic 23 square miles, you’ll find a laid-back, country — yet affluent —vibe. Incorporating two hamlets – Sarle’s Corners and Scott’s Corners, the town of Pound Ridge features a compact business district, including a few restaurants, antiques shops, and an indie bookstore. Pound Ridge also boasts the county’s largest park, the 4,700-acre Ward Pound Ridge reservation, which it shares with Cross River.

Scarsdale. Photo by Alex Caroll

Scarsdale

With a median income of $250,000, Scarsdale is Westchester’s wealthiest town. Conveniently located near the Bronx River Parkway, Scarsdale adheres to strict zoning intended to maintain its quant, Tudor-style downtown. The town’s renowned school district produces average SAT scores hundreds of points higher than the national average.

Somers

With large areas of open land, Somers offers a country feel. Bordering Putnam County, the town has many fruit farms, offering farm-fresh produce, pumpkin picking in the fall, and cut-your-own Christmas trees during the holidays. The Elephant Hotel, built by Hachaliah Bailey (the creator of the Bailey Circus), was so named after Bailey bought one of America’s first elephants and toured with menageries of exotic animals. Today, the hotel serves as the Somers Town Hall.

Yorktown

Yorktown lies at the convergence of suburbia and quiet country living. There are five hamlets within the town: Mohegan Lake, Shrub Oak, Crompond, Jefferson Valley, and Yorktown Heights. The town houses the headquarters of IBM’s research facilities, the renowned Eero Saarinen designed Thomas J. Watson Research Center. Residents gather at the Jefferson Valley Mall and the Cortlandt Town Center for virtually all their shopping and entertainment needs.

– Villages –

Ardsley

As part of the town of Greenburgh, Ardsley is a quiet village with a series of small strip malls scattered across Saw Mill River Road. It offers a surprising helping of diverse and popular dining spots — like prime pizza purveyors Stagioni and Ardsley Cucina; the award-winning L’inizio or local fave La Catena; Asian from Golden Wok and Umami; Ardsley Diner; or Sunshine Bagels, which doles out some of the better bagel-and-doughnut fare in Westchester. Throw in Riviera Bakehouse and a DeCicco & Sons, and Ardsley emerges as the little foodie village that could.

Briarcliff Manor

Education is a priority for this tiny, picturesque village that embodies the apotheosis of small-town living in America, boasting a public-school district that has been ranked among the top 100 in the nation.

Bronxville

Sporting a hefty property-tax burden (even by Westchester standards), Bronxville is nonetheless a quintessentially charming village with a luxe lifestyle, just 36 minutes by train to Grand Central. Bronxville public schools are among the best in the nation, housed in single building close to its downtown.

Buchanan

This small village, located in the town of Cortlandt, was known as East Haverstraw during Colonial times. Comprising 1.4 square miles, Buchanan is heading into a new era of opportunity and development once the Indian Point Nuclear Plant shutters in 2021, positioning it as a potential red-hot property for rising real-estate value.

Croton-onHudson

With abundant green space and enviable river views, Croton is well-known for the Clearwater Music Festival, the oldest and largest music and environmental festival of its kind in the region. Visitors and residents alike are drawn to Croton Gorge Park for impressive views of the Croton Dam and spillway. Favorite destinations of its small downtown include the Blue Pig Ice Cream Shop and The Black Cow Coffee Company.

Dobbs Ferry

Here, river views, a quant village vibe, and an eclectic dining scene meet. Foodies can indulge in creatively topped hot dogs at Dobbs Ferry Dawg House, Japanese food with a cult following at Sushi Mike’s, and Sunday roast at The Rare Bit. There’s also star chef David DiBari’s The Cookery and The Parlor, which are considered among the best restaurants in the county. For scenic outdoor recreation, visit the Old Croton Aqueduct Trailway for a jogging and biking route that overlooks the Hudson.

Elmsford

Both Captain Lawrence Brewing Company, and the Westchester Broadway Theatre call this one-square-mile village home. Elmsford offers a host of sports and leisure venues for children and youth, including Sport Time USA, the Westchester Skating Academy, Bounce U, and The Westchester Gym, the site of one of Westchester’s only ninja-warrior training courses. Elmsford also served as a location for the Showtime series Homeland.

Harvest-on-Hudson in Hastings-on-Hudson. Photo by Simon Feldman

Hastings-on-Hudson

Named by early British settlers inspired by its resemblance to Hastings in England, the village’s hilly areas overlook the Hudson and feature Tudors, manor houses, and ranches. This waterfront village has long been home to Nobel Prize winners and famous writers, such as Richard Dresser and Kevin O’Rourke. Its downtown emanates an artsy feel, with yoga studios, a record store, and a plethora of independent shops. Notable restaurants include Harvest on the Hudson, offering romantic farmhouse dining, Saint George Bistro, serving French bistro fare, and Taaim Falafel Shack, serving affordable Middle Eastern cuisine.

Irvinton’s Red Hat on the River. Photo courtesy of Red Hat on the River

Irvington

This historic village was once home to the great American author Washington Irving and features unique landmarks, including Irving’s home, Sunnyside, and the Armour-Stiner Octagonal House. Follow its tree-lined Main Street down toward its scenic Hudson River waterfront. There, you’ll find excellent dining options, such as MP Taverna, serving Greek delicacies, Red Hat on the River, serving new American fare, and Sambal, serving Thai and Malay food.

Katonah. Photo by Stefan Radtke

Katonah

Katonah is a pristine, historically preserved village that has maintained its original character through the centuries. Upscale, bucolic, and culturally rich, the village features open green space, fine examples of Victorian architecture, and a central business district adjacent to its railroad station. Katonah is home to the Katonah Museum of Art, the Caramoor Center for Music and the Arts, numerous art galleries, and the John Jay Homestead.

Larchmont

Named after its abundance of the larch trees, Larchmont is widely recognized as a Tree City USA. Take in the village’s greenery in one of its many serene parks, including the 27-acre Flint Park and Manor Park, the latter with spectacular views of Long Island Sound. Its charming downtown is brimming with antique stores, art galleries, boutiques and dining destinations geared towards its well-heeled residents.

Village of Pelham

Considered New York City’s first bedroom community, the village of Pelham has a rich history, dating back to before the Revolutionary War. Today, the .8-square-mile tract features a host of Colonials and Victorians, an art-house cinema and art center, and great dining. It also features a park inspired by Manhattan’s High Line: a historic railway track, the Highbrook Railway Bridge, is being transformed into a park and walking path.

Pelham Manor

This tiny yet upscale Sound Shore village lies on the southernmost border of Westchester County, next to the Bronx. Pelham Manor is the summer home of the New York Athletic Club at Traver’s Island. With a smaller population than its sister village, Pelham, it offers nearby shopping options, including a vast Fairway Market, Lane Bryant, and Marshall’s Shoes.

Pleasantville. AdobeStock/Dinara

Pleasantville

Located in the heart of the County, Pleasantville may well be the most aptly named place in the county. It is a charming, 1.8-square-mile village within the town of Mount Pleasant. This walkable village is full of tree-lined streets, just 30 miles from Manhattan, and has a robust shopping-and-dining corridor — all just 15-minutes or less from White Plains to the south, Mount Kisco to the north, and the Rivertowns to the west. Visit its numerous independent shops, restaurants, weekly farmers’ market and definitely the renowned Jacob Burns Film Center, which offers diverse educational programming and screenings of independent, art-house, foreign, and documentary films.

Eugene’s Diner & Bar in Port Chester. Photo by Chris Perino

Port Chester

Part of the town of Rye, the village Port Chester boasts a spirited downtown area buoyed by high-end rental developments, such as The Castle, and a $6 million train-station renovation. Yet, the real estate in Port Chester is still comparatively affordable, and the diverse dining scene — driven by such hotspots as bartaco, Saltaire, Eugene’s Diner and Sonora — have resulted in the village being unofficially dubbed “the foodie capital of Westchester,” featuring cuisine offerings from across the globe. Meanwhile, the historic Capitol Theatre offers classic rock, jazz, and pop-music performances by recording-industry icons, while the waterfront mall features a 14-screen movie theater, Costco, Bed, Bath & Beyond, and a Stop & Shop.

Rye Brook

There may be no actual downtown, but its revamped Rye Ridge Shopping Center – filled with independent stores and chic boutiques – will fulfill most of your shopping and dining needs. Try Fortina’s for pizza, Buddha for sushi, and the Rye Ridge Deli for classic Jewish deli fare. Rye Brook is also home to imposing office complexes, as well as the stunning 35-acre Crawford Park, with its renovated pavilion, playground, and sensory garden.

Sleepy Hollow

Every October, this historic village — made famous by Washington Irving’s 1820 short story “The Legend of Sleepy Hollow” — becomes a Halloween mecca, attracting visitors with its Halloween parade and block party, haunted hayrides, and the nightmarish-yet-fun Horseman’s Hollow. The historic Sleepy Hollow Cemetery — the resting place of such notables as John D. Rockefeller, Brooke Astor, Washington Irving, and Andrew Carnegie — offers the opportunity for serene, bucolic, daytime hikes.

Tarrytown

Ranked by Forbes as one of the prettiest towns in the U.S., ethnically diverse Tarrytown offers breathtaking views of the Hudson, Palisades, and Manhattan, and a 35-minute express train to Grand Central. This walkable village features historic architecture and diverse dining options – including Korean, Portuguese, Greek, Japanese, and good-ol’ slow-smoked barbecue. Unique to Tarrytown are the Lyndhurst gothic revival mansion, built in 1838 by Jay Gould, and Kykuit, majestic home to four generations of the Rockefeller family. Other Tarrytown attractions include the 19th-century Tarrytown Music Hall and the three-year-old Jazz Forum Club.

Tuckahoe

Quaint and friendly Tuckahoe in the town of Eastchester manages to squeeze in two train stations, a bustling village square, and a tiny Main Street within its 0.6 square miles. Grab a bite at The Quarry Restaurant or The Tap House for pub grub, or pay Mamma Assunta, Roma, or Angelina’s a visit for hearty Southern Italian fare. The Tuckahoe real estate market is especially hot in recent years, offering expanding housing opportunities, walkability, diversity, and affordablility compared with other areas in Westchester.

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