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A Lifetime of Loving Gilleys

Vintage Pics
Category: Vintage PicsTag: Food & Drink, Transportation

Photos of one of Portsmouth’s oldest dining institutions

We all have our Gilley stories. Mine are legion and most not fit for publication. The first time I partook of a Gilley dog and beans the rolling restaurant was parked in Market Square.  

I went home and used my father’s woodworking tools to design a pull-toy in the shape of the wagon. I dreamed of making my living selling wooden Gilley carts to the tourists. I made two, a laborious process with my father’s shopsmith, then realized I was no craftsman. And yet the dogs and burgers and fries keep coming. They have sustained me through many long winters living downtown. Where else could one dine after turning a newspaper article at 2 a.m.? Half a century later, it’s still my go-to guilty pleasure.

This classic image shows Ralph Gilbert and Harold Clark. “Gilley” was an employee who worked for the Kennedy family, the owners, for five decades. He passed away in 1986. The food wagon received a nightly ticket from the police for parking illegally until it moved to its stationary spot on 175 Fleet Street in 1974. This is the earlier Kennedy cart, built in 1916 and seen here in 1937. It was originally towed into town by horse-cart, and later, by this 1922 tractor. The current Gilley Wagon is the only surviving example of five custom-made diners built in 1940.

Below are two more historic images of the lunch wagon. Photos courtesy POrtsmouth Athenaeum.

Gilley’s Lunch Cart parked in the South End (Portsmouth athenaeum Collection)
Ralph “GIlley” Gilbert
Gilleys Cart in Market Square
Proposed 2026 upgrade to Gilley’s from McNabb Company
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