Montauk didn’t develop like your typical town. Driving into Montauk is like entering another world entirely—with water views on each side and wild landscapes. For 250 years Montauk was pastureland for cows and sheep. Then it was a fishing village and became more developed in the early 20th century as it was going to be turned into a summer resort town, but the developer went belly up.
Now there are many old Montauk buildings that have been transformed into new establishments. Examples of this adaptive reuse are the Navy Beach Restaurant; the Montauk Brewing Company; and the Montauk Playhouse. Navy Beach used to be a torpedo testing ground, while Montauk Brewing Company was a woodworking shop. Montauk Playhouse was originally two indoor tennis courts and has undergone partial renovation into a gymnasium and community center.
Navy Beach is the most historic of these three examples. It was a Navy outpost in World War II. Before that it was a fishing village that was around since the turn of the century. In September 1938, half of the fishing village was destroyed by the most powerful hurricane to hit Long Island in history. Nine people were swept away. People put the fishing village back together, only to have it torn down by the Navy in 1942. They were given 30 days to vacate their shacks for a torpedo testing range. Some of the buildings were moved, but the Navy tore down everything else and built four massive buildings covering 20 acres of shoreline including barracks, which were disguised as a New England fishing village from above. These were eventually turned into Rough Riders Landing Condos stands on this site, next to the Navy Beach Restaurant. The Navy also poured concrete roadways and infrastructure that still serve the area today.
Fort Pond Bay was particularly suitable for testing torpedoes. They were manufactured not far away at the Newport Rhode Island naval facility and then they were assembled and tested in Montauk. There were stories of mishaps with the torpedo testing range during the war effort. The torpedoes were launched without warheads, as they had not been perfected yet. They boomeranged and turned back around to where they were launched from and smashed up docks and houses—one landed on the back of a flatbed truck and the owner joked that he didn’t remember picking that up. Eventually, the Navy perfected the torpedoes and they were able to track the serial numbers to find out which enemy ships were blown up in Japan. It was a point of pride that Montauk successfully contributed to the war effort.
Today, Navy Beach Restaurant is located where the Navy base used to be and has been serving lunch and dinner on the beach since 2010. The food is excellent, and the décor looks like an old nautical building with porthole windows looking onto the water. The building housed several different restaurants before, having been converted in the 1980s. It was part of the original complex of the Navy base housing. There’s also a building with a tall chimney that served as a cannery to can food for the Navy.
Montauk Playhouse was built in 1928–29 by Carl Fisher as the Montauk Tennis Auditorium below the Montauk Manor Hotel. It’s a Tudor Revival structure built of light steel frame construction sheathed in plywood and covered in stucco with a fieldstone base. There are two main gable-roofed volumes, which were the two tennis courts symmetrically arranged around a low shed, which housed common spaces. After being tennis courts, it held boxing matches, and in the 1950s it served as a theater, hence the name “Playhouse.”
Today, the Playhouse is a community center housing the Body Tech private gym, a physical therapist office, adult daycare and meals for the elderly and a childcare center. There’s also a full-size gymnasium occupying one of the former tennis court bays, the only one in Montauk. These were the result of a $7 million bond with construction completed in 2006. There’s a $5 million fundraising effort to build a pool and aquatic center in the other tennis court bay, which currently stands empty. Montauk Brewing Company is a relatively recent addition to the Montauk village. The building has been standing since 1996, first as a woodworking shop owned by the father of one of the Brewery’s founders, Vaughan Cutillo. Cutillo approached his father upon his retirement from the woodworking business to see if he and some friends could turn the building into a brewery. The town of East Hampton took two years to give them a permit to convert the garage-like structure into a fully operational brewery. The rest, as they say, is history.