Five Historic Estates We Love in Upstate New York

Amid the natural beauty and quaint inns, it can be easy to forget that upstate New York is rich with history, as well as a veritable haven of gorgeous houses from bygone days. Dotted along the Hudson River are the homes of prolific writers and famous families, from American author Washington Irving to the powerful Rockefellers. Most of these homes have since been turned into historic landmarks and fine museums, and many are an easy trip from New York City. With summer on the horizon, excursions to these houses and grounds make for a perfect city escape — one that will bring you back in time and transport you to the regal and grand upstate New York of the 19th century.

Ever Rest
Home of Jasper Cropsey
5 Historic Homes We Love in Upstate New York.
5 Historic Homes We Love in Upstate New York.

Ever Rest was the residence and studio of Hudson River School painter Jasper Cropsey and his wife, Maria. Built in what was then called Hastings-Upon-Hudson (now Hastings-on-Hudson) in the 1830s by local industrialist William Saunders, the couple moved into the gothic style home in 1885. Jasper dubbed the home “Ever Rest” with the hope being that the two would live out their twilight years there — and so they did. Their granddaughter, Isabel, inherited the property after they passed and lived there until she died as well. In 1977, the home was entered into the National Register of Historic Houses and today it is a museum. A very short and easy trip from Manhattan, about 30 minutes by car and 40 minutes by Metro North train, tours of the home and studio are available by appointment and on weekdays only. Tours do not take place in August, December, or January.

Local Recommendations
Shop: maisonette
Eat: Boro6

23 miles from New York City
Accessible by car, train

Images by Newington-Cropsey Foundation

Home of Washington Irving
5 Historic Homes We Love in Upstate New York.
5 Historic Homes We Love in Upstate New York.

Sunnyside was the quaint cottage home of 19th century writer Washington Irving, best remembered for his short stories The Legend of Sleepy Hollow and Rip Van Winkle, two tales firmly rooted in the landscape of upstate New York. In his own words, Irving described Sunnyside as “a little old-fashioned stone mansion, all made up of gable-ends, and as full of angles and corners as an old cocked hat.” The home, which sits on the banks of the Hudson River, is today a museum and remains as it was when Irving lived there — which he did until his death — with many of his possessions on display, including his partners’ desk, his favorite Voltaire chair, and his walking stick. Frequent daily tours of the house and bucolic grounds are scheduled between May and early November with the whole visit lasting about an hour. If you’re coming from Manhattan, the train is your fastest bet as the Metro North to Irvington from Grand Central takes just over 40 minutes.

Local Recommendations
Shop: Seasons on the Hudson
Eat: Red Hat on the River

Irvington, NY
31 miles from New York City
Accessible by car, train to taxi

Images by Bryan Haeffele and Historic Hudson Valley

Home of The Rockefellers
5 Historic Homes We Love in Upstate New York.
5 Historic Homes We Love in Upstate New York.

Built in 1913, Kykuit has been home to four generations of Rockefellers, the first of whom was Standard Oil founder John D. Rockefeller, once the richest man in America. The six-story stone house is a historic landmark today, and the expansive grounds and sculpture gardens alone are worth the visit. Tour the main rooms of the house while admiring the work of artists like Pablo Picasso, Henry Moore, Alexander Calder, Louise Nevelson, and David Smith among others. Explore the underground art galleries that house Governor Rockefeller’s collection of Picasso tapestries, and the cavernous Coach Barn with its collections of classic automobiles and horse-drawn carriages. Learn the stories that highlight the lives of Rockefeller family members and their contributions to philanthropy, conservation, business, government, and the arts. Open Thursdays through Sundays in the summer, garden tours, house tours, and grounds tours are available, and if you’re making the quick trip to Sunnyside, it’s more than possible to do both landmarks in one day, especially if you take the express Metro North train to Tarrytown.

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Shop: Pretty Funny Vintage
Eat: Blue Hill Cafe & Grain Bar

Sleepy Hollow, NY
32 miles from New York City
Accessible by car, train to taxi

Images by Jaime Martorano

Home of Ogden Mills and Ruth Livingston Mills
5 Historic Homes We Love in Upstate New York.
5 Historic Homes We Love in Upstate New York.

Home to early 20th century businessman Ogden Mills and his wife, Ruth Livingston Mills, Staatsburgh was passed down for generations as the Livingston Family were big landowners in the Hudson Valley during the 17th century. Inherited by Ruth in 1890, the Mills family commissioned a prominent architectural firm from New York City to enlarge and embellish the home, turning it into a Beaux-Arts mansion with 65 rooms and 14 bathrooms. The couple was known to entertain up to 80 guests at a time and left the property to family members after their death. In 1938, a descendent of the family donated the home and its 192 acres to the State of New York. Located two hours from the city atop a bluff overlooking the Hudson River, the mansion can be visited throughout the year and offers numerous events, many of them themed historical tours.

Local Recommendations
Shop: Hammertown
Eat: The Amsterdam

Staatsburg, NY
100 miles from New York City
Accessible by car

Images by Andrew Halpern and Kirk Guida

Home of Frederic Church
5 Historic Homes We Love in Upstate New York.
5 Historic Homes We Love in Upstate New York.

Take the scenic train ride up to Hudson to explore Olana, the 250-acre artist designed landscape of esteemed Hudson River School painter Frederic Church. Considered a national treasure and one of the most visited homes in New York, Olana’s main house is beautiful, yet hard to classify due to its unique blend of styles. Built in the mid-19th century after Church and his wife, Isabel, returned from a trip to Europe and the Middle East, the couple designed the home to blend Victorian architectural elements with decorative Middle Eastern motifs. Arched window openings, balcony woodwork, and tile work are just a few of the influences they took with them from cities like Beirut, Jerusalem, and Damascus. Though the family lived in the home for many years, Church continued to work on it for the rest of his days. The house is surrounded by carriage roads and a stunning landscape to picnic on while taking in views of the Hudson River. Tickets book fast to tour the home itself, so be sure to make your reservations ahead of time as there will be a wide selection of talks, courses, and special tours taking place throughout the summer.

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Shop: Hawkins New York
Eat: BackBar

Hudson, NY
130 miles from New York City
Accessible by car, train to taxi

Images by Beth Schneck and Andy Wainwright