Long Island, thrusting 125 miles eastward from New York Bay to a point abreast of New London, Connecticut, faces the New England coast across Long Island Sound on the north and fronts the open Atlantic on the south. The long, narrow outline of the island resembles that of a whale…

State 27, called the Sunrise Highway to Oakdale and the Montauk Highway east of there, links the mainland villages of the South Shore and parallels the Outer Barrier, the long beach that extends from Brooklyn to Southampton. The western communities of the South Shore are New York City suburbs; the central ones are farming and residential villages; the eastern ones are swanky summer resorts and deep-sea angling bases.

—New York, A Guide to the Empire State (WPA, 1940)

Located on the South Shore of Long Island, New York, present day Massapequa is a hamlet, having a total area of four square miles and a population of approximately 22,000 people. Notable residents have included Jerry Seinfeld, Alec Baldwin, Brian Setzer and Candy Darling.

After stumbling upon pictures of the All American Hamburger Drive In, I made it my business to hop on the Long Island Rail Road (LIRR) for Massapequa, now otherwise known (to me) as “Americana heaven.” A sleepy suburban town with one foot planted firmly in the past, Massapequa serves up nostalgia the minute you get off the train.

Guide Notes

  • Krisch’s Restaurant and Ice Cream Parlor. 11 Central Avenue. Originally opened in 1920s Bay Ridge, Brooklyn, Krisch’s found a home in Massapequa in 1955. A winner for Best Ice Cream on Long Island in the Long Island Press, they are famous for their homemade ice cream, pies and chocolates, their classic soda counter and full menu. The exterior original neon sign is a stunner.
  • Fairfield Elementary School. 330 Massapequa Avenue between Merrick Road and Sunrise Hwy. Erected 1925.
  • All American Drive-In. 4286 Merrick Road. All American, dating to 1963, has remained in the hands of the Vultaggio family since its inception. The outside structure retains a space-age aesthetic of the 1960s. Not only is the building squarely stopped in time but the menu appears to have changed little in both content and price. The fries are delicious and ring in at around $1.25. (I witnessed four grown men, post baseball game, purchase a meal for $19.95.)
  • Massapequa Bowl. 4235 Merrick Road. Family owned and operated since 1960.
  • The Massapequa Diner. 4420 Sunrise Hwy. A short walk from Krisch’s and established in 1950, the Massapequa Diner prides itself on being “not just a touchstone in the early coffee-drinking career of Jerry Seinfeld,” but a diner with fresh, well-prepared food. It is also rumored to have been a meeting place of Roy DeMeo, capo in the Gambino crime family, portrayed by Ray Liotta in the 2012 film, The Iceman: The True Story of a Cold-Blooded Killer.
  • Within view of the Long Island Railroad station, at 2162 Veterans Blvd, is the Elks Lodge, a charming 1960s building whose sign beckons visitors to Tuesday morning bingo at precisely 10:15am. The Elks have been doing service for this community for more than 50 years.
  • Massapequa Station typifies the elevated Babylon Branch stations on the Long Island Railroad. It was originally part of the South Side Railroad of Long Island, built in 1867 as South Oyster Bay station. The station you see today was rebuilt in 1953.

* * *

Northeast Regional Guide LEAH FRANCES was born in a small fishing village off the west coast of Canada and raised in Victoria, British Columbia. In pursuit of a graphic design career she moved to New York City in 2005 and now calls Crown Heights, Brooklyn, home. She spends her days in the production departments of magazines and her evenings studying at the International Center of Photography. Weekends you will find her in the back of a Greyhound bus, map in hand. Leah posts daily at

Phil's Pizzeria & Restaurant - Hicksville Road in Massapequa, NY

I just dug up this pic Alex sent me months ago of Phil’s Pizzeria in her hometown of Massapequa. It’s a mac and cheese pie with pretzel crust. I don’t normally like pretzels, but this I have to try! Stay tuned…