Montauk is immensely rich with American history. Odds are, you may already know about our famous Montauk Point Lighthouse, commissioned by President George Washington–but what about the other historic sites Montauk has to offer? The next time you #VisitMontauk, consider diving deep into some of the fascinating history all across Montauk. These historic places of interest are among those in the USA deemed worthy of Preservation and are listed on The National Register of Historic Places.
Interested in learning more about Montauk’s rich indigenous and colonial history? Consider visiting the Montauk Historical Society and the Montauk Library for more historic archives and images.
1. Caleb Bragg Estate at Gurney’s Star Island Resort
Designated 1987
Originally 8 buildings built on 4.2 acres on Star Island in 1929 and eventually incorporated into the Montauk Yacht Club. Caleb Bragg was an entrepreneur, speed boat racer, and race car driver in three Indianapolis 500 races where he met Carl Fisher.
Caleb Bragg Estate, 2009. Photo courtesy of Wikipedia.
Montauk Yacht Club, 2024. Photo courtesy of the Montauk Yacht Club.
2. Deep Hollow Ranch
Designated 1658
Birthplace of the American Cowboy, many visitors are surprised to learn that the USA’s oldest operating cattle ranch resides right here in Montauk. Annual cattle drives began in 1658 from west of East Hampton out to Deep Hollow Ranch, about 4 miles east of Montauk town. Today, visitors enjoy trail and beach rides through the historic property.
Cooper’s Deep Hollow Ranch in the 1940s. Photo courtesy of the Montauk Library.
Deep Hollow Ranch, family-owned & operated by the Keogh family today. Photo courtesy of Deep Hollow Ranch.
3. The Montauk Manor
Designated 1984
The Montauk Manor is the only one of three Grand Hotels planned by Carl Fisher in the 1920s to be built. Today, it is a 140-room condominium resort set on 12 acres overlooking Montauk.
The Montauk Manor, after completion in 1927. Photo courtesy of the Montauk Manor Resort.
The Montauk Manor today, photo courtesy of Lessing’s Hospitality Group.
4. The Montauk Playhouse
Designated 1988
A Carl Fisher building, the Montauk Playhouse opened in 1929. In its lifetime, it has served as a tennis emporium, performing arts center, boxing arena, military base, and movie theatre. The completion stages of the 20-year renovation began in 2024 to add a cultural arts and aquatic center.
Original Montauk Manor Playhouse, circa 1930, Photo courtesy of the Montauk Playhouse Community Center Foundation.
Montauk Playhouse as of 2023, prior to new construction. Photo courtesy of Montauk Playhouse.
5. HMS Culloden Shipwreck Site
Designated 1979
The HMS Culloden was a 170-foot Royal Navy frigate which ran aground and sunk 150 feet off what is now named Culloden Point in Montauk on January 24, 1871. She was burned to the waterline and abandoned. Scattered debris can be found buried in the sand and treasure hunting is prohibited. The ship’s cannon is now on display at the East Hampton Town Marine Museum in Amagansett.
Site of H.M.S. Culloden shipwreck site in Culloden Point. Photo courtesy of the Montauk Library.
Illustration of H.M.S. Culloden. Photo courtesy of the Montauk Library.
6. AN/FPS-35 Radar Tower and Antenna, Camp Hero
Designated 2002
Camp Hero was originally named Fort Hero (Army) in 1942 after Major General Andrew Hero, Jr., who was the Army’s Chief of Coast Artillery between 1926 and 1930. The Radar tower became operational in December 1960. The reflector is 126 feet long and 38 feet tall weighing 40 tons. It was the second one ever built and it is now the last one standing.
The Radar tower at Camp Hero circa 1980. Photo courtesy of the Montauk Library.
The Radar tower at Camp Hero circa 2006. Photo courtesy of New York Times.