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Wimpys

@wimpysofcapecod

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American Cuisine & Casual Dinning
508.428.6300

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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.

#Osterville #Wimpys #CapeCod #OstervilleVillage #OldCape taken in Osterville, Cape Cod, MA by @wimpysofcapecod

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24 days ago

Great news - we get one more summer with @wimpysofcapecod in town! taken in Osterville Village by @wimpysofcapecod

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7 months ago

Since 1938, Wimpy’s has been part of the heart of Osterville. What began as a small hamburger counter grew into one of the village’s most beloved gathering places - known for its fireside dining, welcoming tavern, bustling market, and dedication to community, hospitality, and food quality. Over the decades, it has remained deeply rooted in Osterville and in the lives of generations of families.

After nearly nine decades in the center of town, Wimpy’s will be closing this April, with their next location still to be determined.

An agreement is in place with the group behind @pateschatham - a well-regarded American restaurant in Chatham - to redevelop the site and build a new, high-quality restaurant for Osterville. To clarify, there are no plans for condos or office space - the vision is for a single, thoughtfully designed restaurant.

Change is never easy when it involves a place tied to so many memories, family dinners, and celebrations. We thank Wimpy’s for the decades of service they’ve given this community and wish them the very best in what comes next.

If anyone knows of a great potential new location for Wimpy’s, feel free to share suggestions - many would love to see them continue nearby.

#Osterville #Wimpys #OstervilleVillage #CapeCod #CapeCodEats taken in Osterville Village by @wimpysofcapecod

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8 months ago

taken in Wimpy's Seafood Cafe & Market by @wimpysofcapecod

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a year ago

Awesome October Day on Sampsons Island today. 😎 by @wimpysofcapecod

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a year ago

Spicy Comfort Food You Say?

Blackened Chicken Pasta - Now available at Wimpy's!

752 Main St.
Osterville, Ma 02655 by @wimpysofcapecod

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3 years ago

Street Lights.. People.. Munchin on our Boursin Burger.. Garlic.. French Fries.. Tonight!

Angus beef / caramelized onion jam / Boursin / arugula / garlic French Fries.. by @wimpysofcapecod

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3 years ago

It's always the perfect time of year for the Salty Hostess Margarita!

Wimpy's Seafood Cafe
752 Main St.
Osterville, Ma 02655 by @wimpysofcapecod

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3 years ago

This week's appetizer special - (while supplies last)

Fish Tacos - Atlantic cod / purple and green cabbage / pineapple salsa / adobo sauce - $14

Wimpy’s Seafood Café – 752 Main St., Osterville, Ma. 508-428-6300. Visit us at Wimpysseafoodcafe.com by @wimpysofcapecod

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4 years ago

This week's special soup -
Vegetarian Butternut Squash Bisque - Taylor Farm squash / shaved parmesan, house crouton, balsamic drizzle - $7 cup / $9 Bowl

Wimpy’s Seafood Café – 752 Main St., Osterville, Ma. 508-428-6300. Visit us at Wimpysseafoodcafe.com by @wimpysofcapecod

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4 years ago

This week's pasta special - (while supplies last)

Bay Scallop Aglio Olio - Nantucket bay scallops / toasted garlic / mushroom / green onion / shaved parmesan $38

Wimpy’s Seafood Café – 752 Main St., Osterville, Ma. 508-428-6300. Visit us at Wimpysseafoodcafe.com by @wimpysofcapecod

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4 years ago

Starting on Tuesdays & Wednesday’s in March Wimpy’s Will be offering Twin Lobsters for $25.99 Lunch & Dinner ( Dine in Only ) no splitting allowed. Can not be used together or in conjunction with any other on going promotions. See you soon! by @wimpysofcapecod

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7 years ago