A Westchester Landmarks Guide: Historic Estates, Art, and the Great Outdoors
Beyond the busy downtown of White Plains, Westchester County unfolds into one of the richest collections of landmarks in the Northeast. Along the Hudson River sit the historic villages of Sleepy Hollow, Tarrytown, and Irvington, steeped in colonial history and literary legend. To the north lie sprawling preserves and working farms; to the east, world-class art and classic beaches on Long Island Sound. Together they make Westchester a place where a short drive can carry you from an 18th-century mill to a modern sculpture garden.
This guide gathers ten of the county's most rewarding landmarks, chosen from across its river towns, parks, and shoreline. From the cemetery that inspired an American ghost story to an island that once hosted the biggest bands of the swing era, each destination shows a different side of Westchester.
Whether you are planning a day trip or you already live here, these landmarks are worth knowing. Each one links to a closer look, so you can plan a visit and discover the stories behind the places that make the county special.
Table of Contents
1. Sleepy Hollow Cemetery in Sleepy Hollow, New York
Sleepy Hollow Cemetery spreads across ninety acres of rolling hills above the Pocantico River, a garden cemetery that doubles as an outdoor museum of American history. Established in 1849, it is the real setting behind Washington Irving's famous tale and the resting place of some of the nation's most prominent figures.
Winding lanes lead past Victorian mausoleums, hillside monuments, and the graves of Irving, Carnegie, and Chrysler, with the historic Old Dutch Church burying ground alongside. Guided tours, especially the autumn evening walks, are the best way to take in its history.
Best Time to Visit
Fall, for peak foliage and the popular evening tours.
Spring, when the grounds are green and quiet.
Weekday mornings, for the most peaceful walks.
Guided tour days, for the full history from an expert.
Highlights
Famous graves: Washington Irving, Andrew Carnegie, and Walter Chrysler among them.
The Old Dutch Church: an adjoining colonial burying ground tied to Irving's tale.
Guided tours: daytime and lantern-lit walks led by historians.
2. Philipsburg Manor in Sleepy Hollow, New York
Philipsburg Manor is a restored 18th-century farm and milling complex where costumed interpreters and a working water mill bring colonial New York to life. Run by Historic Hudson Valley, it centers the story of the enslaved Africans who lived and labored on the site.
A visit takes you across a wooden footbridge to a working gristmill, a stone manor house, and grazing heritage animals. It is immersive, honest, and especially lively during its popular autumn events.
Best Time to Visit
Autumn, for Horseman's Hollow and seasonal events.
Summer, for harvest festivals and hands-on history days.
Weekday mornings, for a quieter tour.
Check the schedule, as the site is seasonal.
Highlights
The working gristmill: water-powered and still grinding grain.
Living history: costumed interpreters and heritage farm animals.
An honest story: interpretation centered on the site's enslaved community.
3. Washington Irving's Sunnyside in Irvington, New York
Washington Irving's Sunnyside is the whimsical riverside cottage of America's first internationally famous author, who designed nearly every inch of it himself. Wisteria-draped and full of character, it looks like something out of one of his own stories.
Preserved by Historic Hudson Valley, the house and its romantic gardens sit on a wooded slope above the Hudson. Costumed guides lead tours through Irving's study and parlor, much as he left them.
Best Time to Visit
Spring and summer, when the gardens are in full bloom.
Fall, for foliage and Irving-themed programs.
Weekdays, for smaller tour groups.
Check the schedule, as hours are seasonal.
Highlights
The cottage: a storybook home Irving shaped himself.
Riverside gardens: winding paths and Hudson River views.
Guided tours: costumed interpreters sharing Irving's life.
4. Stone Barns Center in Pocantico Hills, New York
Stone Barns Center is a nonprofit working farm and food-education center set in handsome stone barns from the former Rockefeller estate. It is also home to Blue Hill at Stone Barns, one of the most acclaimed farm-to-table restaurants in the country.
Visitors can walk the fields, meet pastured animals, and peek into greenhouses, all a living demonstration of sustainable farming. Tours, classes, and seasonal events round out the experience.
Best Time to Visit
Spring and summer, when the fields are in full production.
Fall, for the harvest and seasonal events.
Wednesday through Sunday, as the farm closes early in the week.
Book Blue Hill and events far in advance.
Highlights
A working farm: pastured animals, heirloom crops, and greenhouses.
Blue Hill: a world-renowned farm-to-table restaurant on-site.
Historic barns: Rockefeller-era architecture with a modern mission.
5. Rockefeller State Park Preserve in Sleepy Hollow, New York
Rockefeller State Park Preserve offers more than 1,700 acres of woodlands, meadows, and lakes threaded by over 45 miles of gently graded carriage roads. Built by the Rockefeller family and now open to all, they make for some of the finest and easiest walking in the region.
Highlights include the scenic Swan Lake loop near the entrance and the Thirteen Bridges Trail deeper in the woods. It is a haven for hikers, runners, riders, and birders in every season.
Best Time to Visit
Fall, for brilliant foliage across the hills.
Spring and summer, for wildflowers and long walks.
Winter, for quiet, snow-dusted trails.
Weekday mornings, to beat the crowds.
Highlights
Carriage roads: 45+ miles of smooth, scenic trails.
Swan Lake: a tranquil, easy loop near the entrance.
Wildlife: a favorite among Westchester birders.
6. Jacob Burns Film Center in Pleasantville, New York
Jacob Burns Film Center is a nonprofit cinema and media-arts center devoted to independent, foreign, documentary, and classic film. Housed in a restored 1925 movie palace, it has become one of the Hudson Valley's leading cultural institutions.
Its calendar mixes curated screenings, festivals, and visiting filmmakers, while a nearby Media Arts Lab teaches filmmaking to all ages. For film lovers, it is a destination and a community.
Best Time to Visit
Year-round, as programming runs continuously.
Festival and premiere nights, for guests and special events.
Weekend matinees, for a relaxed outing.
Check the calendar, as the lineup changes often.
Highlights
A restored theater: the historic 1925 Rome Theater, beautifully updated.
Curated film: independent, foreign, and documentary cinema.
The Media Arts Lab: filmmaking classes for every age.
7. Croton Point Park in Croton-on-Hudson, New York
Croton Point Park covers roughly 500 acres on a peninsula reaching into the Hudson, with water on three sides and some of the widest river views in the county. It offers a beach, a campground, trails, and meadows, plus a deep and layered history.
One of the few places in the lower Hudson Valley where you can camp beside the river, it is also a prime spot for winter bald eagle watching. History runs deep here, from Native American sites to old vineyards and brickyards.
Best Time to Visit
Summer, for the beach and riverside camping.
Winter, for bald eagle watching along the Hudson.
Spring and fall, for hiking and birding.
Weekends, though reserve campsites well ahead.
Highlights
A Hudson peninsula: sweeping river views on three sides.
Riverside camping: a rare chance to camp by the Hudson.
Winter eagles: one of the region's best eagle-watching spots.
8. PepsiCo / Donald M. Kendall Sculpture Gardens in Purchase, New York
PepsiCo Sculpture Gardens surround the company's Purchase headquarters with 45 monumental sculptures set across 168 landscaped acres. Free and open to the public, it is one of Westchester's true hidden gems.
The collection features works by Calder, Moore, Rodin, and other giants of modern sculpture, placed within formal gardens, ponds, and open lawns designed as a single work of art. A leisurely walk takes an hour or two.
Best Time to Visit
Spring through fall, when the gardens are open on weekends.
Weekend mornings, for a quiet, unhurried walk.
Warm, clear days, for the best of the outdoor setting.
Confirm the seasonal calendar before you go.
Highlights
World-class sculpture: 45 works by Calder, Moore, and Rodin.
A designed landscape: gardens, ponds, and lawns as art.
Free admission: open to the public at no charge.
9. Rye Town Park & Oakland Beach in Rye, New York
Rye Town Park & Oakland Beach has welcomed families to the shore of Long Island Sound since the early 1900s. With a sandy public beach, a historic promenade, and shaded picnic grounds, it offers a classic, old-fashioned seaside day.
Built as one of the first public parks designed to give families access to the shore, it retains its Gilded Age charm. It also sits right beside Playland, making Rye's waterfront a full-day destination.
Best Time to Visit
Summer, for swimming and the full beach experience.
Weekdays, for a quieter, more relaxed beach day.
Shoulder seasons, for peaceful walks on the promenade.
Early mornings, before parking and sand fill up.
Highlights
Oakland Beach: a 1,200-foot sandy beach on the Sound.
A historic promenade: early-1900s waterfront architecture.
Next to Playland: combine a beach day with the amusement park.
10. Glen Island Park in New Rochelle, New York
Glen Island Park is a 105-acre island retreat on Long Island Sound, reached by a short bridge from the New Rochelle shore. With a beach, a marina, and shaded picnic groves, it delivers a genuine island getaway minutes from the mainland.
The park also carries a glamorous past: it was home to the famous Glen Island Casino, where Glenn Miller and other swing-era bands played to national radio audiences. Today it is a peaceful county park with sweeping water views.
Best Time to Visit
Summer, for the beach, marina, and picnicking.
Near sunset, for the best water views.
Weekdays, for a quieter island visit.
Check seasonal hours and parking before you go.
Highlights
An island escape: 105 acres reached by bridge, surrounded by the Sound.
Big-band history: the former home of the famed Glen Island Casino.
Waterfront recreation: a beach, marina, and shaded groves.
Why These Westchester Landmarks Stay With You
From the misty lanes of Sleepy Hollow Cemetery to the windswept shoreline of Glen Island, from the carriage roads of Rockefeller Preserve to a bucket of just-picked produce at Stone Barns, Westchester rewards anyone who takes the time to explore beyond the main roads. A quiet morning walk around Swan Lake. The golden light on the Hudson from Croton Point. A summer afternoon on the sand at Oakland Beach. These are the experiences that stay.
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Explore the county. Take your time. Westchester will introduce itself one landmark at a time.
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