This city of nearly 70,000 residents has neighborhoods that range from quaintly suburban to densely urban. There are three Metro-North Stations and several shopping districts. The city hosts events such as the Arts on Third Festival, one of the largest arts and entertainment festivals in the county.
Known as the “Queen City of the Sound,” the city boasts miles of Long Island Sound shoreline. Between estates on private islands, older homes on quiet suburban streets, and urban skyscrapers downtown, housing options are diverse. New Rochelle is home to both Iona and Monroe College, as well as historical sites like Execution Rocks Lighthouse and Leland Castle and fun destinations like the 105-acre Glen Island Park and New Roc City, an entertainment and cinema complex complete with an IMAX theater, mini-golf course, and an arcade.
Between Hudson River waterfront views, art galleries, and live-in artist work lofts, Peekskill is the ultimate arts destination. The Hudson Valley Center for Contemporary Art regularly features exhibitions and programs, while Paramount Hudson Valley offers live entertainment, drawing in top comedy acts and musical performers. Throughout the year, trendy java joints like the Peekskill Coffee House and the BeanRunner Café host open mic nights for musicians to perform. Don’t miss the Hudson Hop & Harvest Festival in the fall, featuring locally brewed craft beer and live music.
Although it’s the smallest city in Westchester, tony Rye does not fall short of activities. Playland amusement park is easily the city’s most renowned destination, complete with the famous Dragon Coaster and old-fashioned boardwalk. Picturesque Oakland Beach stretches down the Long Island Sound, and Rye’s downtown district along Purchase Street is nearby for upscale shopping and dining.
Commercial center by day, White Plains is a hub for corporate offices and shopping, including two major malls: The Westchester and The Galleria, as well as a freestanding Bloomingdale’s. After dark, its nightlife scene surfaces with a number of bars, pubs, and lounges. Top-notch dining options are clustered around Mamaroneck Avenue, within walking distance to the luxurious Ritz-Carlton, Westchester.
The fourth most populous city in New York State, Yonkers sits right at the border with the Bronx. Ridge Hill and the Cross County Shopping Center serve as major shopping destinations within the city; both are outdoor malls with renowned retail and dining options. Empire City Casino at Yonkers Raceway has harness racing and a casino with 5,300 slot machines. Nearby is the Hudson River Museum, where you can find six art galleries, a planetarium, and the historic Glenview Mansion museum. Dine at Chef Peter Kelly’s X2O Xaviars on the Hudson at the historic Yonkers pier.
Photo by Sonja Lovas
This chic rural haven, known for its miles of trails and horse-grazing pastures, offers residents the peace and quiet of tranquil countryside life. The town consists of three hamlets: Bedford Village, Bedford Hills, and Katonah—the most notable—which features destinations like Muscoot Farm, Caramoor Center for Music and the Arts, and the Katonah Museum of Art. Celebrities like Bruce Willis, Ralph Lauren, Ryan Reynolds and Blake Lively, and Martha Stewart make their homes here. The queen of living well has been a Bedford resident since 2000, while actor Richard Gere is a co-owner of the quaint Bedford Post Inn.
Defined by its many wooded hills, streams, and wetlands, this rural north-county town sits partially along the Hudson River, just south of Putnam County. Cortlandt is divided into two villages, Croton-On-Hudson and Buchanan, and multiple hamlets, including Montrose, Crugers, and Verplanck. The Cortlandt Town Center, which has a Walmart, big-name retail clothing stores, and a movie theater, is a favorite among locals.
The villages of Bronxville and Tuckahoe make up this family-friendly town. Spend the day out with the kids at Twin Lakes County Park or Interlaken Reservoir, or enjoy one of the county’s best burgers at Piper’s Kilt. Eastchester is an educational hub with award-winning public school districts and Concordia and Sarah Lawrence College campuses (both in Bronxville).
Greenburgh’s 36-square-mile border includes a whopping six villages—Ardsley, Dobbs Ferry, Elmsford, Hastings-on-Hudson, Irvington, and Tarrytown—and three hamlets: Fairview, Edgemont, and Hartsdale. Visit the impressively modern Greenburgh Public Library in Elmsford, one of the biggest libraries in the Westchester Library System. Foodies will want to visit the Westchester Greenhouses & Farms for fresh produce. The hamlet of Hartsdale includes Poets’ Corner, a neighborhood of neatly groomed 1950s ranch houses and Cape Cods built on 26 streets named for illustrious poets.
Modest homes as well as a multitude of large estates, gated communities, and private country clubs constitute this south-county town. Within it is the hamlet of Purchase, home to the corporate headquarters of MasterCard and PepsiCo and two college campuses: Purchase College and Manhattanville College. While you won’t find a downtown shopping district in Purchase, Harrison has shopping and restaurants along Halstead Avenue.
This rural town borders western Connecticut, arching over the hamlets of Cross River, Goldens Bridge, South Salem, and Waccabuc. Lewisboro is known for its scenic charm with horse farms, riding trails, wooded fields, and seven lakes. Mountain Lakes Park and the Ward Pound
Ridge Reservation span hundreds of acres, offering plenty of space for hiking, biking, camping, and fishing.
Photo by June Marie
Nine miles of this town’s beachy Long Island Sound coastline are lined with marinas, yacht clubs, and shorefront parks. Inland, you’ll find a vibrant town known for its antique and vintage furniture and accessory stores, as well as trendy boutiques and mainstay eateries like Sal’s Pizza and Walter’s Hot Dog Stand. The town includes two villages—Larchmont and Mamaroneck.
Although spanning just three miles, Mount Kisco is packed with shopping destinations and a variety of dining options. Find large department stores like Target and Kohl’s, chain retailers like Gap and Ann Taylor, and locally owned standouts like Wilson & Son Jewelers, Heller’s Shoes, Beehive Designer Collective, Blithewold Home, and Churchills. Choose from Greek, Indian, Italian, and Mexican restaurants all close by. Café of Love, Winston, Village Social, or Little Drunken Chef are a few to try.
With a total area of more than 24 square miles, Mount Pleasant encompasses the Village of Pleasantville and the eastern portion of Briarcliff Manor. Its several hamlets include Hawthorne, Pocantico Hills, Thornwood, and Valhalla. Visit Stone Barns Center for Food & Agriculture in Pocantico Hills for a tour of the farm and seasonal activities, or take a stroll around the impressive Kensico Dam in Valhalla.
Comprised of the affluent hamlets of Chappaqua and Millwood, New Castle is famous for its top-notch school district, quaint little towns, and celebrity residents, including Bill and Hillary Clinton, Ben Stiller, and Vanessa Williams. Some of the homes here are historic, dating back to the days of the Revolutionary War. While in Chappaqua, check out the area around King Street for local food and shopping experiences such as Susan Lawrence Gourmet Foods, Local Ice Cream, and Family Britches.
A cohesive blend of rural and suburban living, homes within North Castle’s hamlet of Armonk sit on large plots of land, and the village is always bustling with its good eats and high-end boutiques. The town also includes the hamlets of Banksville and North White Plains. Visit Wampus Pond for scenic walks year-round and ice skating come cold weather. In September, check out The Armonk Outdoor Art Show, a gathering of more than 185 local 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.
Home to the Sing Sing Correctional Facility since 1826, this Rivertown contains two villages: the Village of Ossining and a part of Briarcliff Manor. Ossining’s Hudson River waterfront has several marinas and three boat clubs. On a clear day, residents are able to see the Manhattan skyline on the horizon. Also notable is Teatown Lake Reservation, a 1,000-acre reserve with 15 miles of hiking trails and diverse habitats as well as Wildflower Island, a sanctuary for more than 230 native and endangered wildflower species.
Within its 23 square miles, you’ll find a country vibe among the hamlets of Sarles Corners and Scotts Corners. It’s an affluent town filled with several restaurants, antique shops, and even Westchester’s largest park, Ward Pound Ridge Reservation, which spans 4,300 acres into Lewisboro.
Westchester’s wealthiest town, Scarsdale has a Tudor-style downtown district lined with trendy boutiques, cafés, and restaurants. Beautiful homes and massive estates lie on the outskirts of the town, still in reach of Scarsdale’s stellar school district (SAT score averages reach hundreds of points higher than the national average).
Bordering Putnam County, Somers offers a country feel with large areas of open land. Visit Stuart’s Fruit Farm for fresh produce, pumpkin picking, and apple cider donuts in fall or to cut your own Christmas tree during the holidays. Historic to the town is the Elephant Hotel, built by Hachaliah Bailey between 1820 and 1825 (he brought one of the first elephants to America and toured with menageries of exotic animals). Today, the hotel stands as the Somers Town Hall.
Yorktown residents enjoy country pleasures with the convenience of suburban living. There are five hamlets within the town (Mohegan Lake, Shrub Oak, Crompond, Jefferson Valley, and Yorktown Heights). The Jefferson Valley Mall and the Cortlandt Town Center fulfill residents’ shopping and entertainment needs.
As part of the town of Greenburgh, this tiny village spans only one square mile. While the town itself isn’t bustling, the series of small strip malls down Saw Mill River Road offer a cohesive mix of independent shops, chain stores, and top foodie destinations like Riviera Bakehouse, La Catena, and L’inizio.
Ranked in 2014 by www.safechoicessecurity.com as the safest place to live in New York State, Briarcliff Manor offers a small-town setting with upscale amenities close by. This tiny village prioritizes education; its public school district is ranked among the top 100 in the country, and the village has one of Pace University’s campuses within its border. It’s also home to the award-winning Trump National Golf Club.
Previously home to Joseph and Rose Kennedy, this picturesque, affluent village maintains a reputation for luxurious living—with a 36-minute Metro-North commute to Manhattan. While the village spans only one square mile, its downtown area is vibrant and extensive with a variety of restaurants, bars, and independent shops. Bronxville’s public schools are among the best in the nation and are all housed in one building, close to the village’s downtown area.
Located within the town of Cortlandt, this village (known as East Haverstraw during colonial times), comprises 1.4 square miles. It’s home to Indian Point Energy Center, which produces 10 percent of the state’s electricity.
An artsy Rivertown with relatively affordable housing stock, Croton offers an abundance of public parks from which to admire its waterfront views and abundant green spaces. Visit Senasqua Park for picnics on the Hudson, Croton Point Park for the annual music-in-support-of-the-environment Clearwater Festival, or Croton Gorge Park for breathtaking views of the Croton Dam. The village has a small downtown with neighborhood eateries like Memphis Mae’s and Ocean House, as well as standouts The Blue Pig ice cream shop and The Black Cow Coffee Co.
Part of the town of Greenburgh, Dobbs Ferry offers single-family homes plus a handful of condos and co-ops in close proximity to its downtown. There, you’ll discover a busy dining scene, speckled with a few independent shops—the perfect college town for students at nearby Mercy College. For outdoor enjoyment, visit the Old Croton Aqueduct Trailway, a scenic jogging and biking route, or one of the village’s many parks: Memorial, Gould, or Waterfront Park, overlooking the Hudson.
A hot spot for local businesses because of its numerous office parks, Elmsford is a working-class community with a modest downtown strip. Destinations like Westchester Skating Academy, Sportime USA, and the Westchester Broadway Theatre offer distinct entertainment experiences.
Known for attracting successful writers, artists, and academics, this river village is home to playwright Richard Dresser, actor Kevin O’Rourke, fine art printer Ben Diep, and multiple Nobel Prize winners. The downtown area has an artsy vibe with a noticeable absence of chain stores. It’s home to a vinyl-record store, gluten-free bakery, a handful of excellent restaurants, and several yoga studios.
This historic riverfront village was once home to the great American author Washington Irving. Visit landmarks open for public viewing, such as the Stiner-Ross House, McVickar House, and Washington Irving Memorial. Along the tree-lined thoroughfare, which slopes down toward the Hudson, you’ll find dozens of local businesses and eateries. Dine at one of the many restaurants with waterfront views, like Sambal, Il Sorriso, MP Taverna, or Red Hat on the River.
Named after its abundance of larch trees, Larchmont is widely recognized as a “Tree City USA” for its lush, natural beauty. Admire the village’s greenery in one of its many quiet parks, including the 27-acre Flint Park or scenic Manor Park with gazebos, nature trails, benches, and spectacular views of the Long Island Sound. The charming downtown is replete with antique stores, art galleries, boutiques, and dining destinations.
Part of the town of Pelham, this tiny, well-to-do village lies on the southernmost border of Westchester County next to the Bronx. With a smaller population than its sister village, Pelham, it maintains a preppie vibe. Various shopping and dining options are close by and easily accessible at Post Road Plaza, featuring a 75,000-square-foot Fairway Market, Dave & Buster’s, Marshall’s Shoes, HomeGoods, Lane Bryant, and Smashburger. You’ll also find the New York Athletic Club at Travers Island, where members can participate in a wide variety of athletic programs.
Art enthusiasts flock here for exhibits at the Pelham Art Center. The Picture House, a renovated 1920s theater showing mainstream, arts, and indie films, hosts a film club with critic Marshall Fine and special screenings with big-name actors like Ryan Reynolds and George Clooney.
Located in the center of the county, Pleasantville is a charming village within the town of Mount Pleasant. Its downtown district is always bustling with visitors, who can stroll down its tree-lined streets and pop in and out of its numerous independent shops and restaurants and visit its bustling farmers’ market on Saturday. Well known to the village is the Jacob Burns Film Center, which regularly shows independent, foreign, and documentary films.
A village with a city-like feel, Port Chester offers a lively downtown area with an abundance of restaurants. Its culinary scene is vibrant with an array of cuisines to choose from, including Mexican, Peruvian, Colombian, Brazilian, French, Italian, and Indian. The village is home to the Capitol Theatre, a music venue where rock ‘n’ roll legends have performed and modern musicians still do. Also in Port Chester is The Waterfront, a mall featuring a 14-screen movie theater, Costco, Bed Bath & Beyond, Stop & Shop, and a range of dining options.
While you won’t find a historic downtown or train station in this Westchester village, the newly revamped Rye Ridge Shopping Center should service all your shopping and dining needs. It’s filled with trendy independent stores like Lv2bfit and Indigo Chic Boutique, along with eateries like Fortina, Buddha, Chipotle, and Chop’t. Rye Brook is also home to the 35-acre Crawford Park, which has softball fields, a playground, and the Crawford Mansion—rentable for special events.
The setting for the spooky tale “The Legend of Sleepy Hollow,” the town has embraced its identity as a Halloween town. Come October, the village celebrates in style with haunted hayrides past the Old Dutch Church, Horseman’s Hollow (which includes an appearance by the Headless Horseman), and the Sleepy Hollow Festival of Witches. Historic sites abound as well, such as the Rockefeller’s Kykuit estate, colonial Philipsburg Manor, and Sleepy Hollow Cemetery—where notables like John D. Rockefeller, Brooke Astor, Washington Irving, and Andrew Carnegie are buried.
Anchored by a slew of antique shops and farm-to-table restaurants, this Rivertown exudes a fun energy and earthy vibe. Many single-family homes and townhouses have been built along the Hudson River, and they afford breathtaking views of the water and the Tappan Zee Bridge. Unique to Tarrytown is Lyndhurst, a historic Gothic Revival mansion built in 1838. Also standing since the 19th century is the 843-seat Tarrytown Music Hall, where a range of performers have graced the stage, including Ani DiFranco, BB King, Cyndi Lauper, Gregg Allman, Michael Bolton, Norah Jones, Tony Bennett, and Wynton Marsalis.
Although spanning less than one square mile, Tuckahoe manages to squeeze two train stations, a bustling Village Square, and an old-timey Main Street within its borders. Notable stops include Growlers Beer Bistro, Roma Restaurant, Martine’s Fine Bake Shoppe, and the Westchester Italian Cultural Center.
Population: www.city-data.com; Median Household Income: based on 2010-2014 American Community Survey 5-year Estimates on www.factfinder.census.gov; Median Home Sale Price: Houlihan Lawrence; Median Property Taxes: Mary Beth Murphy, Westchester County Tax Commission; # of Houses Sold, Average # of Days on Market: Houlihan Lawrence; Property and Violent Crime Rate: www.bestplaces.net; Average Commute to Grand Central and Train Stations: Metropolitan Transit Authority; Main School District and Public High Schools: www.trulia.com
#: There are multiple numbers in certain columns because of Cortlandt’s two school districts. *In cases where a town is served by multiple school districts, the district tax rates were averaged. **Property crime, on a scale from 1 (low crime) to 100. Offenses include burglary, larceny-theft, motor vehicle theft, and arson. The US average is 43.5.
***Violent crime, on a scale from 1 (low crime) to 100. Composed of four offenses: murder and nonnegligent manslaughter; forcible rape; robbery; and aggravated assault. The US average is 41.4