Westchester County Voyage Tips and guide

Contents

Westchester County is a county of New York State in the New York metro area. It lies to the immediate north of the New York City borough of the Bronx. A number of its villages and towns serve as bedroom communities for commuters to New York City, but Westchester itself is also open for business. Pepsico, IBM, MasterCard, Reader's Digest and other prominent corporations have their headquarters here. But it's not all work and no play. There's plenty to see and do in the county.

• 41.14-73.841 Briarcliff Manor – a village shared by two towns. Home to many wealthy families, Trump National Golf Course, Sleepy Hollow Country Club, and a number of historic buildings and districts. Historic sites include All Saints' Episcopal Church, Juniper Ledge, and the Scarborough Historic District.
• 41.1589-73.77222 Chappaqua – a pretty and well-to-do town, home of Bill and Hillary Clinton
• 41.261389-73.90253 Cortlandt – township in the northwest corner of the county, borders the Hudson River and Putnam County. The Old Croton Dam is listed on the National Register of Historic Places.
• 41.2042-73.88614 Croton-on-Hudson – location of popular Croton Point Park, which juts nearly a mile into the river. Also home to Teatown Lake Reservation.
• 41.165278-73.8566675 Ossining – the location of Sing Sing maximum-security prison where New York City mobsters were sent "up the river". Outside the prison walls, Ossining is ranked the #2 best community to live in by Westchester Magazine
• 41.288889-73.926 Peekskill – northernmost city in Westchester with scenic views of the Hudson Highlands.
• 41.1364-73.78757 Pleasantville – no, we didn't make this up; longtime address of Reader's Digest
• 41.0833-73.76678 Valhalla – this hamlet is reputedly named by a devoted fan of Wagner for the heavenly abode in Norse mythology. Today, Valhalla is home to several large cemeteries which are final resting places of many rich and famous people.
• 41.295556-73.8080569 Yorktown – home to the IBM Thomas J. Watson Research Center and the Guiding Eyes for the Blind headquarters. The town hosts a yearly Greasestock festival, a showcase of alternative fuel vehicles.

• 41.225833-73.66510 Bedford – yes, Martha Stewart still lives here. The Bedford Village Historic District, Caramoor Center for Music and the Arts, Palmer-Lewis Estate, and The Woodpile are listed on the National Register of Historic Places.
• 41.258611-73.68527811 Katonah – in 1897 over 50 buildings of the original town were moved a mile or so south to make way for one of New York City's reservoirs. The Katonah Village Historic District, Stepping Stones, and St. Luke's Episcopal Church are listed on the National Register of Historic Places. The John Jay Homestead is listed as a National Historic Landmark.
• 41.238056-73.522512 Lewisboro – though lacking a downtown business district, Lewisboro is rich in natural areas with two Westchester County parks, six town parks and several community preserves.
• 41.203889-73.73055613 Mount Kisco – ostensibly named after local Native American chief Kisco. Now a commercial hub of northern Westchester for shopping and dining with both small businesses and large chain stores like Target, Gap, and Staples.
• 41.2086-73.574714 Pound Ridge – this wealthy town has been the home of many celebrities including Christopher Reeve (Superman).
• 41.328056-73.68555615 Somers – "cradle of the American circus" where Hachaliah Bailey bought an African elephant to use for farm work but it drew such crowds that Bailey took "Old Bet" on the road as a traveling circus. Bailey built the Elephant Hotel in Old Bet's honor and the elephant remains a symbol of the town to this day.

• 41.012778-73.86611116 Dobbs Ferry – quaint Hudson River village. The Estherwood and Carriage House, Hyatt-Livingston House, South Presbyterian Church, and United States Post Office are listed on the National Register of Historic Places.
• 40.991111-73.87416717 Hastings-on-Hudson – Hudson River village has stunning views of the cliffs of the Palisades. Former home to Billie Burke, the "Good Witch" in the Wizard of Oz. Historical sites include the Jasper F. Cropsey House and Studio, the Hastings Prototype House and the John William Draper House.
• 41.034444-73.86555618 Irvington – Named for Washington Irving, who lived nearby at Sunnyside.
• 41.091944-73.86444419 Sleepy Hollow – the very one from The Legend of Sleepy Hollow. Many places in the story can still be visited today like the Old Dutch Church and Cemetery.
• 41.069167-73.85972220 Tarrytown – this Hudson River village is home to several significant historic sites as well as a quaint business district featuring restaurants and antique shops.
• 40.941389-73.86444421 Yonkers – 3rd most populous city in New York state and undergoing major development along the Hudson River. Getty Square, its traditional center only a few blocks east of the river, is down-scale.

• 40.92583-73.7527822 Larchmont – affluent square-mile community on Long Island Sound. Before the automobile, Larchmont was a resort community serving wealthy New York City residents; many of the Victorian "cottages" and a few of the grand hotels remain to this day.
• 40.9492-73.733623 Mamaroneck – name of both a town and a village on Long Island Sound. The exclusive Winged Foot Golf Club has hosted the PGA Championship and several US Opens. Home to Walter's Hot Dog Stand, a Westchester County landmark.
• 40.908611-73.78194424 New Rochelle – home of Iona College and the former College of New Rochelle.
• 40.910556-73.807525 Pelham – a wealthy community of pretty houses, churches and golf courses, it has a short coast on the Long Island Sound and borders the Bronx.
• 41.005-73.66888926 Port Chester – the Bush-Lyon Homestead, Capitol Theater, Life Savers Building, Putnam and Mellor Engine and Hose Company Firehouse, St. Peter's Episcopal Church, and United States Post Office are listed on the National Register of Historic Places.
• 40.9811-73.683927 Rye – upscale city on the Long Island Sound; home of Playland amusement park. Smallest and least city-like of the cities in Westchester; has a small central area with one main street (Purchase Street) and feels much more like a village than anything else.

• 40.94-73.82611128 Bronxville – affluent square-mile community listed in Forbes as one of "America's Most Expensive ZIP Codes". Historic sites include the US Post Office–Bronxville, the Bronxville Women's Club, Lawrence Park Historic District, and the Masterton-Dusenberry House.
• 40.9583-73.808629 Eastchester – former home of a president, John Adams, and vice president, Aaron Burr. Upscale shopping at the Vernon Hills Shopping Center.
• 41.055-73.8230 Elmsford – roughly one mile square, this village is the alleged birthplace of the term "cocktail".
• 41.006944-73.71805631 Harrison – historical places include the Hadden-Margolis House, Stony Hill Cemetery, and United States Post Office.
• 40.914167-73.83055632 Mount Vernon – named after George Washington's home, this is a diverse, largely Black and Latino city undergoing redevelopment as of the early 2020s but with some remaining blighted areas. The Mount Vernon Public Library is the largest public library in Westchester County.
• 41.040556-73.71444433 Purchase – home of a state university with a prominent School of the Arts as well as headquarters for several major American corporations
• 41.0197-73.683334 Rye Brook – contains six main parks totaling nearly 100 acres
• 40.992222-73.78694435 Scarsdale – one of the wealthiest towns in the nation, with residents like Liza Minnelli and Yoko Ono
• 40.9531-73.823636 Tuckahoe – was a major producer of high-quality white marble for the world.
• 41.0325-73.76666737 White Plains – the seat of government for Westchester County, its downtown has been redeveloped with upscale housing and retail. Has two large shopping malls, the Galleria and the Westchester.

Westchester County ranks number two (after NYC) for wealthiest areas in New York State, and is the seventh wealthiest county nationally. Westchester has long been associated with "old money", and some of the country's wealthiest families for generations have lived "upstate" to escape the crowds of New York City but close enough to the Big Apple for business or pleasure. The county maintains its rural appeal with thousands of acres of parks and through a political system of townships containing villages containing hamlets that discourages large cities and preserves small municipalities. Although Westchester is home to nearly one million residents, a village like Briarcliff Manor has a population just under 8,000. Small businesses abound in the towns and villages and you'll need to visit the larger cities and towns like Yonkers, White Plains and Mt Kisco, to find national chain stores and malls.

European settlement of the area began with enormous tracts of farmland held by Dutch manor lords and some of their place names continue to this day, such as Tappan Zee (the Tappan sea), Peekskill (Peek's creek), and Verplank (from van der Planken, near the bridge). Other names honor the Native Americans who lived here like Ossining (from the Sint Sinck tribe), Mount Kisco (allegedly named for Chief Cisqua), and the Kitchiwan neighborhood of Ossining (Kitchiwank tribe).

The political geography of Westchester confuses locals and visitors alike. The county has cities, towns, villages, and hamlets, many of which share names and sometimes overlap. ZIP (postal) codes don't follow municipal boundaries, so the place names in street addresses often don't match the city, town, or village that the address actually resides in.

• Visit Westchester County NY, ☏ +1 914-995-8500, toll-free: +1-800-833-9282, [email protected]. (updated Apr 2021)

• Westchester County Airport (HPN ^IATA) — The biggest airport of the lower Hudson Valley, other than the New York City/New Jersey airports. Tickets can be pricey, but it's oh-so-convenient to arrive smack in the middle of your destination and bypass the traffic around the three major international airports. Rental cars are available.
• John F. Kennedy International Airport, Newark Liberty International Airport, and LaGuardia Airport — The three major international airports in the New York City area offer service to just about anywhere. Westchester-based taxi and livery cars offer regular service to and from the three internationals from most areas of the county. New York City yellow cabs will take to you Westchester in a pinch, but the fares can be exorbitant. If staying in Westchester, ask if your hotel offers shuttle service.

• Amtrak. Some trains make stops at Yonkers and Croton-on-Hudson (Empire Service) and in New Rochelle (Northeast Corridor). However, if you are coming from New York City, keep in mind that Amtrak trains from there are much more expensive than Metro-North to these stops.
• Metro-North Railroad. Three branches of Metro-North Commuter Railroad serve the county, all from Grand Central Terminal:
  • The Hudson Line travels the far west flank of the county along the bank of the Hudson River. For the best views on trains departing from Grand Central Terminal in Manhattan, get a seat on the left side of the train: opposite Yonkers and Hastings-on-Hudson you will be treated to great views of the sheer cliffs of the Palisades.
  • The Harlem Line runs up the middle.
  • The New Haven Line serves communities on the Long Island Sound shore and continues into Connecticut.
• New York City Subway. Termini of several lines to the Bronx are close to the southern edge of Westchester County. From there, you can take a Bee Line Bus to points in Westchester County.

The main Interstate highways leading to Westchester are:

• I-87—named "New York State Thruway" between Westchester and Albany, serves only New York State, from the New York City borough of the Bronx, through the Hudson River Valley and Adirondack Mountains to the Canadian border.
• I-95—named "New England Thruway" in Westchester, serves the length of the U.S.'s East Coast from Miami, Florida, to Maine at the Canadian border.

A few U.S. routes serve Westchester:

• US-1—named "Boston Post Road" or "Post Road" through most of Westchester, largely parallels I-95 and serves the length of the U.S.'s East Coast from Key West, Florida, to Maine at the Canadian border.
• US-6—stretches between Bishop, California, and Provincetown, Massachusetts, serving communities in northern Westchester.
• US-9—named "Broadway" (or "North" or "South Broadway") through much of Westchester, largely parallels I-87 in New York state and runs from Lewes, Delaware through New Jersey, the Hudson Valley, and Adirondack Mountains to the Canadian border.
• US-202—runs from New Castle, Delaware to Bangor, Maine, serving communities in northern Westchester.

• Bee-Line Bus System, ☏ +1 914-813-7777, [email protected]. Westchester County's Bee-Line Bus System provides wide coverage within the county and connects passengers to New York City subway stations in The Bronx. Yonkers and White Plains have the best service overall, with the system being generally densest in the southern portion of the county, but nonexistent in the northeast corner. $2.75, seniors & disabled $1.35, full pricing details. (updated Apr 2021)

It's possible to plan getting around by bus or train, but to make the most of your visit, a car is recommended.

In addition to I-87 and I-95 listed in Get in, Westchester has two auxiliary interstates.

• I-287 (Cross-Westchester Expressway) — connects I-95 in Rye to I-87 in Tarrytown via White Plains. It crosses the Tappan Zee Bridge into Rockland County and continues into New Jersey.
• I-684 — connects I-287 at White Plains to I-84 in Putnam county to the north

Westchester has several parkways, which permit "passenger cars only", no trucks. These roads were built before the rise of interstate freeways. Many are narrow and pass under low bridges, but often traverse scenic, park-like stretches.

• Bronx River Parkway — from the Bronx, through Yonkers, Scarsdale, and White Plains to Valhalla
• Cross County Parkway — from Yonkers to New Rochelle via Mount Vernon
• Hutchinson River Parkway — from the Bronx to the Connecticut border at Rye Brook via Pelham, New Rochelle, Scarsdale, and Harrison
• Saw Mill River Parkway — from Yonkers to Katonah via Hastings, Dobbs Ferry, Elmsford, Pleasantville, Chappaqua, Mount Kisco, and Bedford
• Sprain Brook Parkway — Yonkers to Hawthorne via Ardsley, Greenburgh, and Elmsford
• Taconic State Parkway — from Valhalla it counties north of Westchester via Mount Pleasant, Briarcliff Manor, and Yorktown

In Mount Vernon, be sure to visit Saint Paul's Church, a National Historic Site.

In Tarrytown, you can visit Lyndhurst, "America's most famous Gothic Revival Mansion", and Sunnyside, the home of Washington Irving, author of The Legend of Sleepy Hollow and Rip van Winkle.

Philipsburg Manor is a historic Dutch manor and mill restored to its appearance in the late 17th/early 18th century. You can visit it and Kykuit, the Rockefeller estate when you're in Sleepy Hollow. While you're there, stop by to admire the stained glass windows by Henri Matisse and Marc Chagall at Union Church of Pocantico Hills, and walk through Sleepy Hollow Cemetery, the final resting place of Washington Irving, Andrew Carnegie, Walter Chrysler, and Elizabeth Arden. It also contains the Old Dutch Church and Burying Ground, the churchyard from Washington Irving's The Legend of Sleepy Hollow.

The Hudson River Museum in Yonkers has exhibitions on regional history, Hudson Valley art, and a planetarium.

In Purchase, you can visit the Neuberger Museum of Art, which features modern, contemporary, and African art, and stroll through the Donald M Kendall Sculpture Gardens, which has more than 40 major sculptures amongst 12 outdoor gardens.

Across the entire county is the Taconic State Parkway, where you can drive through beautiful forests during the autumn months.

• Old Croton Aqueduct. Go hiking or biking on the trailway that tops the original (now defunct) water supply to New York City. The trail runs on the western side of the county, passing through Yonkers, Hastings-on-Hudson, Dobbs Ferry, Irvington, Tarrytown, Sleepy Hollow, Briarcliff Manor, Ossining, and Croton-on-Hudson.  
• Visit a farmer's market or farmstand. Farms are scarce in this mostly suburban county, but agriculture is alive and well in the form of farmers markets. Find markets in places like Pleasantville, Tarrytown, Larchmont, Lewisboro, Pound Ridge and Ossining.
• You can still find a few orchards and farms in the northern end of the county that offer pick-your-own fruit and vegetables in season.
• Stone Barns Center for Food and Agriculture, in Sleepy Hollow's Pocantico Hills village, promotes regional agriculture through its educational programs and its demonstration gardens and greenhouses.
• Taste local vintages. There are two wineries in the county. See Pleasantville.
• At Playland in the City of Rye, you can enjoy the historic amusement park (circa 1928).
• Take sailing lessons at the Croton Sailing School, Senasqua Rd, Croton-on-Hudson, +1 800-859-SAIL.
• Rent a kayak, take a guided tour, or launch your own kayak/canoe. Annsville Creek Paddlesport Center, Route 6 & 202, Annsville Circle, Cortlandt Manor, +1 914 739-2588. Good starting point for paddling the scenic Hudson Highlands.
• Follow Ichabod Crane's route. Fans of Washington Irving's Legend of Sleepy Hollow can follow the route of Ichabod Crane from the center of Tarrytown north into Sleepy Hollow. But don't expect to find the "Western Woods" or anything else from the 1999 movie Sleepy Hollow. Tim Burton's production is only loosely based on Irving's story, and was filmed largely in Hertfordshire, England. 
• Oakland beach – Westchester’s own small beach on the Long Island Sound, with restaurant Seaside Johnny’s right on the property.
• Yonkers Raceway Casino and racetrack.

• Art Galleries, Tarrytown. Main Street is home to a few fine art galleries worth experiencing.
• Caramoor, Katonah. Take afternoon tea and tour or attend one of their evening concerts. Mediterranean villa set on an 80 acre estate. Museum, gardens, concerts. 
• Paramount Center for the Arts, Peekskill. Features stage productions, live performances of music and dance, classic films and recent major releases, and visual arts exhibitions.
• Tarrytown Music Hall, Tarrytown. Nonprofit venue regularly hosts jazz concerts, classic movies, and cultural events. Show dates are posted outside the music hall's main entrance and on its web site. 

Explore the county from the perch of a bicycle seat. Moab it isn't, but if you've got a mountain bike you've got your pick of three county parks that sport mountain bike trails. For flatlanders, the Old Croton Aqueduct is a mostly level dirt trail, and the paved North and South County Trailways follow the relatively gentle grades of the old Putnam Line railway. There is a gap between the North and South County Trailways in Elmsford that requires a connection via local streets.

• Bicycle Sundays. May–Oct Su 10AM–2PM. Every Sunday in the summers, the Bronx River Parkway is closed for several hours to provide bicyclists, walkers, and joggers with a 13.1 mi (21.1 km) loop from Bronxville and Yonkers to White Plains. (updated Apr 2021)
• North County Trailway, ☏ +1 914 864-7275. Multi-use paved trail runs 22 mi (35 km) from Eastview in the town of Greenburgh to Somers. The former railroad bridge over the New Croton Reservoir is especially scenic.  
• 41.063333-73.8191671 South County Trailway,, ☏ +1 914 864-7275. Multi-use paved trail runs from Eastview in the town of Greenburgh to just over the Yonkers border. Enjoy a rest stop at one of the benches around Woodland Lake.  
• Blue Mountain Reservation, Peekskill. Seven miles (11 km) of trails in 1,600-acre county park. Trails are marked for level of experience.
• Graham Hills Park, Pleasantville. Five miles (8 km) of trails through a 431-acre county park, geared toward riders with some experience. The park is in the middle of the county at the junction of the Saw Mill River, Taconic, and Sprain Brook Parkways.
• Sprain Ridge Park, in Yonkers. On 278 acres of wooded terrain in the southern end of the county offers trails for beginners as well as advanced.

• Cross County Shopping Center — An outdoor mall in Yonkers.
• The Galleria at White Plains — An enclosed shopping mall in downtown White Plains.
• Jefferson Valley Mall — An enclosed shopping mall in Yorktown in northern Westchester.
• The Westchester — An upscale shopping mall in White Plains.

Westchester has plenty of dining options for many types of cuisine. It has traditionally been known for its Italian-American food at numerous restaurants and pizzerias. For the affluent, Westchester features many fine restaurants with chef graduates from the Culinary Institute of America in Hyde Park, NY or the Institute of Culinary Education in New York City. More budget friendly are old-fashioned diners where everything is on the menu; be sure to ask for the daily specials. You'll find a diner in nearly every village and hamlet. Also widely available are bagels and other foods associated with New York City delis. The ethnic diversity of Westchester gives rise to Portuguese food in Ossining and Tarrytown, Korean in Scarsdale, Greek in Tarrytown (and at many diners throughout the county), and Chinese everywhere. Several towns feature cooking from Mexico, Ecuador, Colombia, and other countries in Latin America. You can also eat Nepalese food in both Yorktown Heights and Scarsdale.

Westchester Magazine publishes a list of best food and drink in the county every year.

For two weeks in March and November, some of the finest restaurants in Westchester participate in Hudson Valley Restaurant Week with a fixed price three-course lunch ($20.14) and dinner ($30.14) that are bargains at top-rated establishments.

For the do-it-yourself crowd, there is also a large number of farmers markets and farm stands in addition to organic markets and ethnic markets for specialty food items.

In 2020, Blue Hill at Stone Barns, an upscale farm-to-table restaurant, was awarded two Michelin stars and was ranked one of the 50 best restaurants in the world.

The city of White Plains contains a number of popular bars and dance clubs located on Mamaroneck Ave. The Irish bars along McLean Ave in Yonkers are popular spots to have a drink at.

For medical, police, or fire emergencies, call 911.

There are numerous hospitals throughout Westchester, including the centrally-located Westchester Medical Center in Valhalla.

The telephone area code for the county is 914. This was shared with other counties until 2000, after which it became Westchester's exclusively.

If you are based in Westchester County, the obvious place to go next is New York City, to the south.

Another option is to drive or take a train further north along the Hudson River, to explore the beauty of the Hudson Valley.

Going east will take you to Connecticut.

Going west will take you to New Jersey or into Rockland County and the Catskills on the other side of the Hudson River.