The Official Page of Osterville Village

October 10 will be Wimpy’s final day in Osterville - closing out an 88-year run in the village where it began.

Wimpy’s isn’t disappearing. It’s moving to the Roadhouse Cafe location in Hyannis, where it plans to remain open year-round. But after nearly nine decades, this is the end of an unmistakably Osterville chapter.
 
The story began in 1938, when Raymond and Winnie Hostetter opened a six-stool hamburger stand, partly to feed telephone workers who had nowhere nearby for lunch. The name came from J. Wellington Wimpy, Popeye’s hamburger-loving character.
 
Those six stools eventually grew into the 200+ seat restaurant generations know today. For roughly 40 years, one specialty was an oversized open-faced cheeseburger topped with onion, tomato, relish, and a single green olive.
 
Raymond and Winnie’s son Vincent “Skip” Hostetter, who grew up in the house behind Wimpy’s, started working there at eight, washing dishes and sweeping floors. He later graduated from the Culinary Institute of America and, after his father died in 1970, helped take over. Skip became known for doing everything from running the kitchen to renovations - even building Wimpy’s long bar from different woods.
 
The Hostetters owned Wimpy’s for 58 years before the Siscoe family bought it in 1996. In 2017, Raymond’s grandson Adam brought it back into the family. Fun fact: Adam also represented the U.S. in snowboarding at the 1998 Winter Olympics, when snowboarding made its Olympic debut.
 
The vintage photo here is from the era when it was billed as “Wimpy’s Restaurant & Tower Club.”
 
By then, Wimpy’s had long been woven into village life. Early Osterville Men’s Club members would gather at the Fox Hole before crossing the street to Wimpy’s for dinner. Generations came for the tavern, seafood market, fieldstone fireplace, family dinners, familiar servers, and traditions passed down through families.
 
For a place that started with six stools, it leaves quite a footprint.
 
Share your favorite Wimpy’s memory below - a go-to meal, favorite server, family tradition, old photo or anything else you’ll remember about the Osterville location.

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