There is no aspect of Westchester that recommends it more highly than its incredible roster of diverse communities.
Whether it’s bustling cities, Rockwellian suburbs, or serene, rustic escapes you seek, the 914 has anything and everything a family, a couple, or an individual could ask for.
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 culture. With a burgeoning arts scene, Mount Vernon had for years hosted such events as The Arts on Third Festival, one of the largest arts-and-entertainment festivals in the county.
Site of the most expansive downtown reimagining in the county, this TOD hotspot is set along majestic miles of Long Island Sound shoreline. The “Queen City of the Sound” 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 Iona University, “NewRo” 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.
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 more recently, Apropos, on the idyllic grounds of the beautifully restored 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.
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.
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, a Saks Off 5th, and three major malls: The Westchester, Galleria, and City Center. Come the evening, a varied nightlife emerges with vibrant 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 as the world-class Kanopi, at The Opus Westchester.
Given its size and proximity to New York City, Yonkers is sometimes referred to as the “Sixth Borough.” Bustling with ongoing riverfront and transit-oriented development, Yonkers is New York State’s third-most-populous city. Offering unique entertainment options, residents and visitors can enjoy both harness racing and Empire City Casino. Yonkers is also home of the Hudson River Museum and planetarium, the historic Glenview Mansion Museum, the spectacular Untermyer Gardens Conservancy, and Lionsgate movie studios. Dine at any of the city’s standout restaurants, like X2O Xaviars on the Hudson, which boasts amazing views of the George Washington and Mario Cuomo bridges.
Celebrities like Martha Stewart, Ralph Lauren, and now Matt Damon call this chic town home, 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 as cultural treasures, like The Caramoor Center for Music and the Arts, Katonah Museum of Art, and the Bedford Playhouse, which features appearances by movie stars, directors, and best-selling authors.
Divided into two villages — Croton-on-Hudson and Buchanan — and multiple hamlets, including Montrose, Crugers, 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.
Comprising the villages of Bronxville and Tuckahoe, Eastchester is an educational hub with award-winning public-school districts, as well as Sarah Lawrence College and Iona University’s satellite campus, both with Bronxville addresses. Local residents rely on longtime standards like the century-old Cornell’s Hardware, Zuccarelli’s Deli, and dining at Ciao, Tosacana, Piper’s Kilt, and Mason Sandwich Co. Locals also love hanging out at the Barnes & Noble’s concept store in the Vernon Hills Shopping Center, and there is a new Saks Off 5th, to boot.
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.
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. Harrison also boasts the first Wegmans grocery store in Westchester County. The Golf Club of Purchase and the A.W. Tillinghast masterpiece Old Oaks Country Club also reside here.
Rural Lewisboro borders western Connecticut and encompasses the hamlets of Cross River, Goldens Bridge, Lewisboro, 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 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 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.
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 of 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.
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 Blue Hill at Stone Barns, 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.
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. 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 Crabtree’s Kittle House and Susan Lawrence Gourmet Foods.
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 itself 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 early fall, check out the Armonk Outdoor Art Show, a gathering of nearly 200 juried artists at the IBM world headquarters.
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 the acclaimed Purdy’s Farmer & the Fish — one of the county’s top restaurants — in the sleepy North Salem hamlet of Purdys.
Home to the storied Sing Sing Correctional Facility since 1826, this burgeoning 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, the Manhattan skyline is visible from the Ossining waterfront. 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 in addition to a wildflower sanctuary.
The result of a 1654 treaty with Siwanoy Indians, Pelham is the oldest town in Westchester. The Picture House, a renovated 1920s theater showing arts and indie films, hosts The Film Club with critic Stephen J. Whitney and special screenings with such big-name actors as George Clooney.
Within its scenic 23 square miles, you’ll find the quintessence of laid-back rustic affluence. Incorporating two hamlets — Sarle’s Corners and Scott’s Corners, Pound Ridge features a compact business district, including a few restaurants, antiques shops, and an indie bookstore. The purported love nest of movie stars Blake Lively and Ryan Reynolds, Pound Ridge also boasts the county’s largest park, the 4,700-acre Ward Pound Ridge reservation, which it shares with Cross River.
With a median income in excess of $250K, Scarsdale is Westchester’s wealthiest town and the second-wealthiest nation-wide, according to Bloomberg and Business Insider. 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.
With large tracts of open land, Somers offers a tranquil, country feel. It borders Putnam County and boasts lots of farm-fresh produce, apple and pumpkin picking in the fall, and cut-your-own Christmas trees when holiday season rolls around. The Elephant Hotel (now Town Hall), built by Bailey Circus founder Hachaliah Bailey, was so named after the Somers native treated America to one of its first elephants (old Bet) and toured with menageries of exotic animals. Somers also contains the hamlet of Heritage Hills, an upscale condo complex with 4,000 residents.
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 is 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.
Every October, this historic village — made famous by Washington Irving’s 1820 short story “The Legend of Sleepy Hollow” — becomes a worldwide Halloween mecca, attracting thousands with its Halloween parade and block party and haunted hayrides. The historic Sleepy Hollow Cemetery — the resting place of such notables as Brooke Astor, Washington Irving, and Andrew Carnegie — offers the opportunity for serene, bucolic, daytime hikes.
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, just 48 minutes from Grand Central by express train. The walkable village features historic architecture and an array of dining options, including Korean, Portuguese, Greek, Japanese, Cuban, 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 Jazz Forum Club.
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. Sidle up to Stephen’s Green for reliable pub grub or pay a visit to Mamma Assunta, Roma, and Angelina’s for hearty Southern Italian fare. The Tuckahoe real estate market has been especially hot in recent years, offering expanding housing opportunities, walkability, diversity, and affordability compared with other areas in Westchester.
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 Umami; Ardsley Diner; or Sunshine Bagels, which doles out some of the better bagel-and-doughnut fare in Westchester. Throw in The Bakehouse, The Shop Ardsley (serving three squares daily), and a DeCicco & Sons, and Ardsley emerges as the little foodie village that could.
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. Briarcliff contains the regal Scarborough Historic District, including Woodlea, the former Vanderbilt mansion that today is the club-house of Sleepy Hollow Country Club.
Bronxville is 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; its median home sale price (roughly $2.7M) is the highest in Westchester. In 2022, Veranda ranked Bronxville 13th among “America’s 20 Richest Towns.”
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 with the closure of Indian Point in 2021, positioning it as a potential red-hot property for rising real-estate value.
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. Local faves include Blue Pig Ice Cream Shop, Black Cow Coffee Company, and the popular seafood spot Ocean House Oyster Bar & Grill.
Here, river views, a quaint village vibe, and an eclectic dining scene converge. Foodies can indulge in locally sourced “farm-to-taco” fare at Tomatillo, Japanese food with a cult following at Sushi Mike’s, and Sunday roast at The Bit. There’s also star chef David DiBari’s The Cookery and The Parlor, both among the county’s best restaurants. For outdoor recreation, visit the Old Croton Aqueduct Trailway for a bucolic jog or bike ride.
Captain Lawrence Brewing Company calls this one-square-mile village home. In addition to a sprawling, 26-building flex/ industrial park, Elmsford offers lots of sports venues, including Sportime USA, the Westchester Skating Academy, Bounce U, and The Westchester Gym, the site of one of Westchester’s only ninja-warrior training courses.
Named by early British settlers inspired by its resemblance to its namesake in England, the village’s hilly areas overlook the Hudson and feature Tudors, manor houses, and ranches. Its downtown emanates an artsy, progressive feel, with yoga studios, a record store, and a plethora of independent shops. Notable restaurants include Harvest on Hudson, offering romantic farmhouse dining amid incomparable views; Saint George Bistro, serving French bistro fare; Boro6 Wine Bar; and Taaim Falafel Shack, serving affordable Middle Eastern cuisine.
This historic village was once home to the great American author Washington Irving and is the current residence of Hollywood royalty Michael Douglas and Catherine Zeta-Jones. The village features unique landmarks, including Irving’s 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 the Greek-themed MP Taverna, the New American fare of Red Hat on the River, and Sambal, serving Thai and Malay food.
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. Many celebrities have called Katonah home over the years, including current resident Martha Stewart.
Named after its abundance of larch trees, beautiful Larchmont has been an Arbor Day Foundation Tree City USA for longer than anywhere else in Westchester. The verdant village includes 27-acre Flint Park and Manor Park, the latter with spectacular views of Long Island Sound. Its charming downtown is brimming with antiques stores, art galleries, boutiques, and dining destinations geared toward its well-heeled and many famous residents.
Considered New York City’s first bed-room 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. Both it and Pelham Manor are a mere half-hour train hop to Grand Central.
This tiny yet upscale Sound Shore village lies on the southernmost border of Westchester County and is the summer home of the New York Athletic Club–Travers Island. With a smaller population than sister village Pelham, Pelham Manor offers nearby shopping options, including a Fairway Market, a BJ’s, Marshall’s, and the trendy Flour Power Bakery.
Located in the heart of the county, Pleasantville may be the most aptly named place in Westchester. 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 15 minutes or less from White Plains to the south, Mount Kisco to the north, and the Rivertowns to the west. It features several indie shops, restaurants, a farmers’ market, and the renowned Jacob Burns Film Center, which offers diverse educational programming and screenings of independent, art-house, foreign, and documentary films.
Part of the town of Rye, the village of Port Chester boasts a spirited downtown area buoyed by high-end rental developments, such as The Castle, and a $6 million train-station reno. Yet, the real estate in Port Chester is still comparatively affordable, and the diverse dining scene — driven by such hotspots as bartaco, Saltaire, and Sonora — have resulted in the village being unofficially dubbed “the foodie capital of Westchester,” featuring cuisines from across the globe. Meanwhile, the historic Capitol Theatre offers classic rock, jazz, and pop performances by industry icons, while the Waterfront mall features a 14-screen movie theater, Costco, Marshalls, Michaels, and Stop & Shop.
There may be no actual downtown, but its revamped Rye Ridge Shopping Center — featuring eateries, boutiques, and a Balducci’s — will meet virtually all of your quick-stop shopping needs. Rye Brook is also home to the heralded Blind Brook school district, ranked No. 45 in the state by Niche.com . Visit the 35 pastoral acres of Crawford Park, with its renovated pavilion, playground, sensory garden, and the all-new Crawford Mansion Community Center.
Related: How to Spend a Perfect Weekend in Katonah