Throwback Thursday – Montauk History on Tap.

Before Frank Tuma Sr. bought the Montauk Tavern 90 years ago, it was run as a sweet shop that “pulled off a clandestine existence during the Prohibition beginning in 1927” — at least according to a story in Dan’s Papers. “The speakeasy survived six years until 1933 when the ban of spirits was finally lifted, and the Montauk Tavern was able trade their lollipops for whiskey.”

Others note that at least a portion of the Main Street building, which was completed in 1927 by the Pearson construction company as part of Carl Fisher’s development spree, did in fact operate as a candy and ice cream store called the Montauk Sweet Shop and Luncheonette. It was run by the Stavropoulos family, who owned Candy Kitchens in Bridgehampton and East Hampton.

“And it was in the early ‘30s that my father then had the restaurant and bar concession in the Manor when it opened,” Vivian Darenberg said of her father, Frank Tuma Sr., in an oral history interview with the Montauk Historical Society. “That was after Prohibition.”

“And then, from there,” she said, “he bought Shagwong Tavern, which at that time was called Montauk Tavern.”

In spite of the Depression, the tavern’s dining space more than tripled by May of 1935, the East Hampton Star reported at the time. “The Sweet shop store, next to the Tavern, has been completely redecorated … and connected through to the Tavern. Meals will be served in the new dining room before Decoration Day.”

A 1936 menu from the Montauk Tavern lists a stuffed lobster platter for $1.50 and a Long Island duckling dinner for $1.25. | Courtesy of the Shagwong Tavern

By the mid-1930s there was music by a live orchestra three nights a week in summer and, in winter, lively social functions like card parties and dances for local Republicans and the Montauk Rifle Club.

Advertisement in The East Hampton Star, July 18, 1935.

Frank Tuma built a bait and tackle shop on the adjoining lot in 1942. In 1946, the tavern was sold to Mary Williams and her husband, Walter Wood, who changed its name. “Watch for the new awnings and canopy soon to appear over the entrance and front of Shagwong Tavern, formerly the Montauk Tavern,” the Star said.

Walter Wood became ill in 1968, and in 1969 Mary Wood sold the tavern to Jimmy Hewitt. The decades that followed are a story of their own, but in 2015, Jimmy Hewitt sold the Shagwong Tavern to Jon Krasner, Beau Campsey, and Jason Behan. The “new regime,” Shagwong’s website says, “continues to bring the infamous free-spirited down and dirty dive bar vibe to the Montauk social scene, as well as fresh local comfort fare all year round.”