Highland Falls, N.Y.: A Cozy Community Next Door to West Point

What do J.P. Morgan, Billy Joel and a pair of innkeepers have in common? A stretch along the Hudson River in the Orange County village of Highland Falls.

That is where, in 1872, Morgan bought and expanded a country estate, whose main house later burned down. In the mid-1970s, Joel rented a property built on the foundations of that house and wrote a song called “Summer, Highland Falls” that is all about ups and downs.

Today, the five-bedroom house is owned by Roxanne and James P. Donnery, who run it as the Overlook on Hudson bed-and-breakfast and have a special room dedicated to Joel. It is the one where he kept his piano, said Donnery, 74, and where he polished “New York State of Mind,” his kiss-off to Los Angeles.

The Donnerys bought the property in 1981, for about $130,000, and raised their four children there. When parents’ weekends at the nearby U.S. Military Academy at West Point put a strain on the local motels, they took in occasional guests.

Four years ago, they transformed the house into year-round lodgings that attract an international cohort. “They come here to kayak, to hike, to bike,” said Donnery, a former Orange County legislator and school board president. Bear Mountain is a few miles south, Storm King Mountain is several miles north, and the river runs between them.

A slim triangle 40 miles from Manhattan, Highland Falls has modestly sized and priced houses, a walkable commercial district and an intimate population of 3,845. The community is so cozy that Kevin Childs, who created a website about the region, was able to devote a section to more than 500 residents’ nicknames.

Donnery’s is Jeepy.

But Highland Falls is best known as the gateway to West Point. The military academy is the village’s main employer (117 jobs for civilians were posted on Indeed in late July, including clerks, nurses and an animal caretaker) and has inspired Chamber of Commerce banners along Main Street that celebrate servicemen and -women.

West Point, in fact, physically encroaches on the village, having annexed 17,000 acres before World War II (some woodlands and parklands were also lost to New York state). With only 4 percent of its taxable land remaining, Highland Falls lobbies, some years quite strenuously, for more than $3 million in annual federal impact aid to support its schools. Squeezed between the academy and the river, it lacks room for development.

This means that Highland Falls is far more like Brigadoon than Shanghai. Its small houses do not face the threat of imminent teardown, and a village Walmart is out of the question. Whether that is a blessing or a curse depends on who you are.

“A lot of people will come and view the homes here, love the village, but they want new construction,” said Bobbie Fallon, the owner of Bobbie Fallon Carousel of Homes, a real estate agency in Highland Falls. “They want four bedrooms and three and a half baths. They may not like to have to commute to Woodbury Commons and down to Rockland County to the big stores and restaurants.”

“Single-family homes are turning into more apartments and two-family homes,” she added. “Businesses have opened and businesses have closed.”

And yet, Pitt said, a 1975 West Point graduate returning for his reunion would easily recognize the village.

“Highland Falls is never going to be a bustling place,” she said. “I don’t even think in its heyday it was a bustling place.”

Highland Falls, along with West Point and the hamlet of Fort Montgomery, is in the town of Highlands. Its half-mile-long Main Street is lined with charming buildings like the 1890s Italianate Village Hall, a former bank building that also houses the police department and historical society. The public library across the street is newer (2001) but no less inviting, with its covered front porch. It offers lectures, story readings, mah-jongg games and musical performances.

Also on Main Street: a clutch of historic churches, two barbershops, an ice-cream parlor, an Irish bar, a Mexican restaurant, a Chinese restaurant, a hardware store, a consignment shop, a McDonald’s and the 62-year-old Park Restaurant. Childs said that his mother waitressed there in her youth and recalled chasing out freshman West Point cadets who had broken regulations by sneaking off “post” and were identifiable by their shoes.

Facing down big-box stores and internet commerce, these businesses are in a precarious state, residents said. They have only minimally benefited from the West Point community, which has its own establishments, and the nearly 3 million tourists who visit the academy each year.

Yet only a few commercial vacancies were evident in early July. A couple of storefronts were even preparing for new tenants, including Carnie’s Eats-N-Treats, which will offer Main Street carnival fare like corn dogs and fried Oreos.

Ladycliff Park, a grassy sliver next to Main Street, is dotted with a few contemporary sculptures. To the west, Roe Park has playing fields, a pond and a flock of somewhat messy geese. (A cutout coyote recently installed there is helping to intimidate them.) The park has been the site of Juneteenth celebrations, Fourth of July fireworks and a free summer recreation program for young children. “It’s also the home of the youth soccer program, men’s softball league, Little League, school sports, private birthday parties, lots of fishing and playground use, and other planned activities like teen movie nights all summer,” Pitt said.

Fallon, the real estate agent, said many of the houses date from the 19th century and the 1920s to mid-20th century. Because the only space for new homes has been on subdivided properties, the homes tend to sit close to one another. But an enclave near the Hudson called Ondaora Park, which was developed in the 1940s from Cragston, the 700-acre J.P. Morgan estate, has bigger lots, Fallon said, and several noteworthy buildings.

Al Sapienza, an actor who has appeared in “The Sopranos” and “House of Cards,” owns one of them, a 1902 house originally built for one of Morgan’s daughters.

Speaking on the phone from Toronto, where he was filming the television series “Suits,” Sapienza, who lives in Manhattan, said he took over the house from his father in 2000 and converted it into 10 apartments that rent for $900 to $2,200 a month.

He prefers to rent to military officers on West Point’s faculty. They are “the best tenants on Earth,” he said. “They fix everything themselves.”

According to Trulia, between March 28 and June 27, 2018, the median sale price of homes in Highland Falls was $142,000, a year-on-year decrease of 12.3 percent. (The fluctuation may be misleading in a small market like this, where only 45 homes have been sold since January.)

Twenty-eight houses, drawn from multiple sources, were listed on Realtor.com as of July 23. The least expensive was a circa 1900 multifamily house with four bedrooms and two bathrooms at 33 Schneider Ave., priced at $140,000; the most expensive was an 1875 house with five bedrooms and three bathrooms at 134 Mountain Ave., priced at $399,000.

The Winhaven Park Community is an 11-year-old town house development across from the village’s Rite Aid. A three-level, two-bedroom property at 17 Winhaven Court. is currently on the market for $279,000.

The median rent as of July 1 was $2,450, according to Trulia.

Highland Falls sends one clear message: You are near the Army now. American flags sprout like dandelions, and the Thayer Gate Deli and Café, near the entrance to West Point, offers “Firstie” and “Plebe” burgers. None of the sculptures in Ladycliff Park have the visual impact of the tank that marks the West Point Museum and visitors center. This imposing complex on the site of the former Ladycliff College, near Main Street, is technically on academy land.

The Highland Falls-Fort Montgomery Central School District is also open to tuition-paying high school students from Garrison, New York, across the Hudson, and high-school-age children of West Point personnel. A current capital project is devoted to improvements to the high school’s athletic facilities and science wing, as well as interior and exterior upgrades. The work is expected to begin next summer.

About 140 students in prekindergarten through second grade attend Fort Montgomery Elementary School, 3 miles south of Highland Falls. In the 2016-17 school year, the student body was 76 percent white, 16 percent Hispanic or Latino and 6 percent black or African-American.

Highland Falls Intermediate School enrolls about 315 students in third through eighth grades and has an average class size of 22. On 2016-17 state tests, 32 percent of the students met standards in English versus 40 percent statewide; 35 percent met standards in math versus 42 percent statewide.

James I. O’Neill High School serves about 480 students in ninth through 12th grades. Average SAT scores for the class of 2017 were 589 for reading and writing and 585 for math, versus 528 and 523 statewide.

The drive from Highland Falls to New York City at rush hour along the Palisades Interstate Parkway takes from an hour to an hour and 40 minutes. A Metro-North train on the Hudson line to Grand Central departs hourly from Garrison, New York, about 10 miles east of Highland Falls. Travel time is about 70 minutes and the price is $13-$27 each way. Coach USA runs a Short Line bus several times a day from Main Street. The trip takes about an hour and 40 minutes to Port Authority Bus Terminal and costs $16.

In 1981, Highland Falls became known as Hometown USA for welcoming the hostages from the U.S. Embassy in Iran, who were bussed through town on their way to the Thayer Hotel in West Point to be reunited with their families after 444 days in captivity. The Town of Highlands Historical Society has a hostage memorabilia collection that it claims is second only to that of the Jimmy Carter Presidential Library and Museum in Atlanta.