From charming main streets to urban delights and tranquil escapes, Westchester combines vibrant culture with natural beauty. We’ve broken down what each town, village, and city has to offer, giving you a closer look at what makes these communities so special.
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 Ramen Musashi and Umami, Ardsley Diner, and Sunshine Bagels, which doles out some of the better bagel-and-doughnut fare in Westchester. Throw in Booskerdoo Coffee & Baking Co. and a DeCicco & Sons, and Ardsley emerges as the little foodie village that could.
Bedford
Celebrities such as Brendan Fraser, Ryan Reynolds, Glenn Close, and Matt Damon have called 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 country life, as well as cultural treasures like Caramoor Center for Music and the Arts, the Katonah Museum of Art, and the Bedford Playhouse, featuring appearances by actors, directors, and best-selling authors.
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. Briarcliff contains the regal Scarborough Historic District, including Woodlea, the former Vanderbilt mansion that today is the clubhouse of Sleepy Hollow Country Club.
Bronxville
Bronxville is a quintessentially charming village with a luxe lifestyle and a short 36 minutes by train to Grand Central Station. Bronxville public schools are among the best in the nation and its median home sale price (roughly $2.7M) is the highest in Westchester. In 2024, Bloomberg ranked Bronxville ninth among America’s 100 Richest Places.
Buchanan
This small village in the town of Cortlandt was called East Haverstraw in Colonial times. Comprising 1.4 square miles, Buchanan is heading into a new era of opportunity and development since the Indian Point Nuclear Plant shuttered in 2021, positioning the village as a hot spot for rising real-estate value, which rose 2.5% between 2024 and 2025.
Cortlandt
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 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 a Walmart.
Croton-on-Hudson
With abundant green space and enviable river views, Croton-on-Hudson has The Blue Pig ice cream shop, Black Cow Coffee Company, and seafood specialist Ocean House Oyster Bar & Grill. Visitors and residents alike are drawn to Croton Gorge Park for impressive views of the Croton Dam and spillway.
Dobbs Ferry
Here, river views, a quaint village vibe, and an eclectic dining scene converge. Foodies can indulge in farm-to-table Amercian fare at Harper’s and Japanese food with a cult following at Sushi Mike’s. There’s also star Chef David DiBari’s The Cookery and The Parlor, both among the county’s top restaurants. For outdoor recreation, visit the Old Croton Aqueduct Trailway for a bucolic run or bicycle ride.
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 and Iona University’s 28-acre campus, both located in Bronxville. Local residents enjoy shopping at Pottery Barn, West Elm, The Fresh Market, and Trader Joe’s, dining at Gigante, Marigold, and Piper’s Kilt, and hanging out at the Barnes & Noble’s concept store in the Vernon Hills Shopping Center.
Elmsford
Captain Lawrence Brewing Company calls this one-square-mile village home. Elmsford offers a lot of sports and leisure venues, including the Westchester Skating Academy, Bounce U, Next Level Athletics, and The Westchester Gym, and is also the site of Westchester Ninja Warrior training courses.
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 Greenhouses & Farm. Poets Corner in Hartsdale is a charming, traditional suburban neighborhood with single-family homes on 26 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 University and Purchase College, which shares a campus with Boundless Adventures, an outdoor-climbing and zipline adventure park. Harrison also boasts the first Wegmans grocery store in Westchester County.
Hastings-on-Hudson
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 fare; and professional pastries aplenty: Aromë Caffé & Patisserie, Antoinette’s Patisserie, and By the Way Bakery.
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 Octagon 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
Katonah is a pristine, historically preserved village that has maintained its original character through the centuries. Upscale, bucolic, and culturally rich, the village features 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, Caramoor Center for Music and the Arts, numerous art galleries, and the John Jay Homestead. Numerous notables have called Katonah home, including Martha Stewart.
Larchmont
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 residents.
Lewisboro
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, dirt roads, 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: 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, accompanied by top performers at swanky Jazz on Main. Shoppers can enjoy big-box stores such as Target, Gap, and Kohl’s, along with local standouts such as Elephant’s Trunk. Mount Kisco also features one of Westchester’s most varied arrays of cuisine options, including Georgian, Greek, Indian, Italian, Mexican, and Turkish, an award-winning bakery, Bella’s Bake Shop, and trendy Exit 4 Food Hall. Wellness seekers will enjoy another of Mount Kisco’s 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 Blue Hill at Stone Barns in Pocantico Hills for one of the world’s top restaurants, or picnic at the plaza located in front of Valhalla’s Kensico Dam.
Mount Vernon
A hub of transit-oriented development (TOD) in the county, Mount Vernon offers its 71,000-plus residents a variety of neighborhoods, from urban areas to traditional suburban enclaves. 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 offers performing and visual arts from jazz to public sculptures, such as the 10th Avenue Bridge Sculpture.
New Castle
Comprising the hamlets of Chappaqua and Millwood, New Castle is known for its top schools, convenient location, and celebrity residents, including Hillary and Bill Clinton, Vanessa Williams, and Ben Stiller. With a walkable downtown, Chappaqua benefits from a renovated Metro-North station and infrastructure-improvement project. Pay a visit to the Chappaqua Performing Arts Center and check out mainstay Susan Lawrence Gourmet Foods or newcomer Bia American Kitchen & Bar.
New Rochelle
Site of the most expansive downtown re-imagining 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, the city 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.
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 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 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 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 La Bastide and Cenadou Bistrot for a top-notch dining experience, in both fine and more casual styles.
Ossining
Home to the storied Sing Sing Correctional Facility since 1826, this Rivertown contains two villages: the village of Ossining and 91% of Briarcliff Manor (the remaining 9% is in Mount Pleasant). Ossining’s Hudson River waterfront has several marinas and three boat clubs. The blossoming food scene includes The Tasty Table, Richie’s Kitchen, and Here Coffee + Beer. The school district has an award-winning science research program and the downtown is rapidly evolving. Also notable is Teatown Lake Reservation, a 1,000-acre reserve with 15 miles of hiking trails, as well as a wildflower sanctuary.
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 140 Kitchen, Fin & Brew, Gleason’s, RameNesque, Taco District, Thaimeless Thai, and Apropos on the idyllic grounds of the restored Abbey Inn & Spa. Cultural and leisure assets include Hudson Valley MOCA, Paramount Hudson Valley Theater, and the 40,000-square-foot Spins Hudson, the largest entertainment venue (including a ropes course and laser tag) on the river.
Offering an artsy, bohemian vibe and striking river views, Peekskill has become an increasingly sought-after, yet affordable place to live. The once industrial city has a thriving art and culture scene and trendy eateries.
Pelham
The result of a 1654 treaty with the Siwanoy people, Pelham is the oldest town in Westchester. The town’s Picture House Regional Film Center, a renovated 1920s theater showing arts and indie films, hosts The Picture House Film Club and special events, some featuring visits from well-known industry professionals.
Pelham (Village)
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, close access to Pelham Bay Park, and a top pie spot in Pelham Pizza. Both it and Pelham Manor are a mere half-hour train hop to Grand Central Station.
Pelham Manor
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 Danny’s Cycles, BJ’s, and bestie-owned Flour Power Bakery.
Port Chester
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 trainstation renovation. Yet, the real estate in Port Chester is still comparatively affordable, and the diverse dining scene—driven by such hotspots as bartaco, Sonora, Run & Hide Brewing Co., Telly’s Taverna, Bona Bona Ice Cream, and The Kneaded Bread—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 performances by industry icons, while the waterfront mall features a 14-screen movie theater, Costco, and Stop & Shop.
Pleasantville
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, 20 or so restaurants, a top-rate farmers market, and the renowned Jacob Burns Film Center, which offers diverse educational programming and screenings of independent, art-house, foreign, and documentary films.
Pound Ridge
Within its scenic 23 square miles, you’ll find the quintessence of laid-back rustic affluence. Incorporating two hamlets—Sarles Corners and Scotts Corners, Pound Ridge features a compact business district, including a few restaurants such as The Inn at Pound Ridge by Jean-Georges, antique shops, indie bookstore Booksy Galore, and Purple Plains, a cannabis boutique. 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.
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, and hometown of 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.
Rye Brook
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 Blind Brook School District, ranked No. 77 in the state by niche.com. Visit the 35 pastoral acres of Crawford Park, with its renovated pavilion, playground, sensory garden, and the Crawford Mansion Community Center.
Scarsdale
With a median income of more than $250K, Scarsdale is tied with Pelham Manor as Westchester’s wealthiest town, and is ranked as the wealthiest suburb nationwide in 2025, according to financial website gobankingrates.com. Conveniently located near the Bronx River Parkway, Scarsdale adheres to strict zoning intended to maintain its quaint, Tudor-style downtown. Besides beautiful parks, eateries, and boutiques, the town has a renowned school district.
Sleepy Hollow
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, haunted hayrides, and the nightmarish-yet-fun Horseman’s Hollow. 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.
Somers
With large tracts of open land, Somers offers a tranquil, country feel. It borders Putnam County and boasts many fruit farms, offering farm-fresh produce, pumpkin picking in the fall, and cut-your-own Christmas trees during the holidays. The Elephant Hotel (today the Town Hall), built by Hachaliah Bailey, a pioneering figure in the menagerie business, was so named after Bailey bought one of America’s first elephants and toured with menageries of exotic animals. Somers contains the hamlet of Heritage Hills, an upscale condo complex with 4,000 residents.
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, just 48 minutes from Grand Central by express train. The walkable village features historic architecture and diverse dining options, including Korean, Portuguese, Greek, Japanese, Cuban, and slow-smoked barbecue. Discover the Lyndhurst gothic revival mansion, built in 1838 by Jay Gould, and Kykuit, majestic home to four generations of the Rockefeller family, also considered to be in Sleepy Hollow. Other Tarrytown attractions include the 19th-century Tarrytown Music Hall and the Jazz Forum night 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. Taste the small plates at Buleria Tapas & Wine Bar, sidle up to Tuck’d Away Bar and Grill, or pay homage to Southern Italian fare at Abruzzese-focused Restaurant ODO, a relative newcomer, or Mamma Assunta, with four-plus decades, and Roma may be Westchester’s oldest pizzeria, with 85 years under its belt. The Tuckahoe real estate market has also been piping hot with housing opportunities, walkability, diversity, and affordability compared with other areas in Westchester.
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, upscale mall The Westchester, and the City Center shopping complex. By night, a varied nightlife scene emerges with vibrant bars, pubs, and lounges. Foodies are drawn to the array of dining options found along Main Street and Mamaroneck Avenue, including Vietnamese, Peruvian, Japanese, classic Southern dining and barbecue, as well as the upmarket Red Horse by David Burke and Kanopi at The Opus Westchester.
Yonkers
Given its size and proximity to New York City, Yonkers is sometimes referred to as the “Sixth Borough.” Blossoming 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 Studios. Enjoy cocktails and dining at the city’s abundant bars and restaurants, like Yonkers Brewing Co., La Lanterna, and Texas de Brazil.
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 for their shopping and entertainment needs.
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