Walking down Main Street in the off-season, one might feel a longing for the bustling summer crowds––smiling bronzed faces with salt-sprayed hair, babies sporting sunglasses being pushed in strollers, children’s hands dripping with melting ice cream––or you may feel the opposite, finding comfort in the quiet sidewalks, empty beaches, and shuttered seasonal businesses, offering a glimpse into the way Montauk once was.
Of the few empty storefronts stands Herb’s Market, which closed its doors for good at the end of September. Harold “Herb” Herbert bought the market in 1963 and ran it with his wife, Chrissy, for nearly 38 years. Previously a grocery store and meat market, the business expanded to include a full delicatessen. The market was known for its specialty sandwiches, fried chicken, prime meats, fresh local produce, and community-hub atmosphere.
The market changed hands twice. For a time, it was owned by Lucille Lenahan and Gillian Mooney, who sold it in 2012 to its last owner, Joe Ferraro. Herb and his family still owned the building and upstairs apartment.
After he retired, Herb recalled his experience as the shop owner in an oral history interview with Joan Lycke from the Montauk Library in 2005. He recalled that one of the downsides to owning the business was the winters: “Winters were long, there was no one here…There were days when you might have six, or seven, or eight customers.”
“And later, I think one of the downsides was getting busier, because you didn’t have the time to do the things that Montauk was so famous for.”
Herb’s passing on August 9, 2026, was a great loss for the community. “To those who knew him, Herb was a true gentleman in every sense of the word. Kind, humble, hardworking, and unfailingly polite. He treated everyone with the same kindness, courtesy, and respect,” his obituary said.
Although the business is shuttered, the windows have been brought to life with a timeline of people, places, and businesses from Montauk’s past. Each window represents a different period from the turn of the 20th century to the 1960s.
Photographs of Montauk’s first dwellings show the landscape as a barren grassland sprinkled with grazing sheep and cattle. Images of Camp Wikoff’s encampment show what life was like for quarantined soldiers returning from the Spanish-American War. The panel on the 1920s depicts Carl Fisher’s vision for Montauk, while the 1940s and 1950s photographs show Montauk’s sportfishing industry on the rise.
Gail and Susan Herbert, Herb’s daughters, created the installation as a tribute to old Montauk using images from the Montauk Library Archives found on New York Heritage Digital Collections. The installation will remain up as the building is being prepped for sale.
Take a walk down Main Street and envision old Montauk for yourself.
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