Wimpy's Leaves Osterville for South Street as Hyannis Prepares to Dig Up Its Downtown
"We chose to do it on a Tuesday, so people who live on Cape Cod would come, the people who have supported us over the years." That's how Adam Hostetter explained to the Cape Cod Times why Wimpy's Seafood Cafe & Market is holding its Osterville farewell on Tuesday, Oct. 6, and not on a summer weekend.
Hostetter's grandparents opened the restaurant in 1938. Choosing a weekday tells you who the owners think the place belongs to. This fall shows where Barnstable's longtime tables end up when their buildings change hands or their leases run out. Two decades-old restaurants on Route 132 are closing for good. The one survivor is moving from Osterville into downtown Hyannis, onto a street the Town is about to rebuild.
Wimpy's has been at 752 Main St. in Osterville since Raymond and Winnie Hostetter opened it in 1938. In 2017, their grandson Adam Hostetter and business partner Jeff Lindsey bought the business back from Karen and Lawrence Siscoe. The Cape Cod Times reported that the lease on what it called the aging building was not renewed. Wimpy's got an extension in March that ran through Labor Day, and then more extensions kept it open daily from 11:30 a.m. to 9 p.m. all summer. No reporting has said why the lease ended or what's planned for the building.
The last day in Osterville is Oct. 10. Four days earlier, the Oct. 6 party rolls prices back to the oldest menu the owners could find. Early coverage mentioned 15-cent burgers. The Oct. 4 Cape Cod Times piece corrected that with Hostetter's itemized list:
The September report said the rollback pricing applies to people dining in. The owners are also collecting donations at the party for Five Bays Preservation, a local environmental nonprofit. No start or end time has been published, so check with the restaurant before you go.
Hostetter has said the name, the favorite recipes, and many of the staff are making the move. That includes the clam chowder recipe from his grandfather, Raymond, and the new menu will add some dishes.
On Oct. 1, the Cape Cod Times named the new home: the former Roadhouse Cafe at 488 South St. in Hyannis, known for its piano bar. Hostetter and business partner Adrian Pryshlak bought the property on Sept. 26 for an undisclosed price. They plan to call it Wimpy's Roadhouse, but the name can't be official until the state Alcoholic Beverages Control Commission approves it. The reopening is expected "later this fall," and no date has been given. In September, before the site was public, Hostetter said the goal was to be closed for "not quite a week." The Oct. 1 story says only "later this fall," so that week-long goal isn't a promise yet.
The same Oct. 1 Cape Cod Times piece notes that the partners already own Fancy's Market in Osterville and The Break Hyannis, across from Hyannis Harbor. So the move adds a second downtown Hyannis restaurant to a group that started in an Osterville village center.
The timing is what stands out. On the day that report ran, the Town of Barnstable announced that its Hyannis Great Streets project would begin construction "within the next few weeks." The project turns the one-way stretches of Main Street, South Street, Ocean Street, and Old Colony Road into two-way streets. It also adds a roundabout at the Six Points intersection of South, Ocean, and Old Colony, plus new shared-use paths along North Street from Stevens Street to West Main Street and along Old Colony Road from South Street to Main Street. The Town expects the two-way conversion to finish "at the earliest by Summer 2027," and state and federal sources are paying for it.
So Wimpy's will reopen on South Street during the same months a Town project is rebuilding parts of that street. The Town's announcement didn't include a detour, parking, or business-access plan. The full plan set and recordings of past public meetings are on the Great Streets Downtown Hyannis project page, and the Town says it will provide updates if the construction schedule changes.
The two closures this year are both on Iyannough Road across from Cape Cod Mall, and neither one is moving.
The IHOP at 790 Iyannough Road closed for good on July 27 after about 40 years.
Up the road at No. 950, Sam Diego's Mexican Cookery and Bar will close on Nov. 15. Its own announcement says the owners spent two years trying to sell the business and the sale never happened. Co-owner Clarke Buchanan told the Cape Cod Times that business has been down since the pandemic, and Boston.com, citing that interview, added the rising cost of the tortillas for the restaurant's free chips. The scale still stands out. The building covers 11,663 square feet, with two bars, two kitchens, four dining rooms, and a summer patio, for about 300 seats. Buchanan says it still serves 500 to 600 dinners on a Saturday night. Compare that with opening night a few days after Labor Day 1982, when Buchanan says the kitchen did 186 dinners. Back then, Sam Diego's was one of the first Mexican restaurants on Cape Cod.
Before Nov. 15 there are two dates to watch. Buchanan says the restaurant's last big bash will be on Halloween, since it has long been a gathering spot that night. He hasn't said whether there will be a costume party. An online auction of the decor and artwork is expected to start in late October. It will include original work by Michael Pinsky, papier-mâché by the Mexican artist Sergio Bustamante, and painted cow skulls. Details will come through a QR code posted in the restaurant and on its social media. The closing announcement also asks guests to come in and use any gift certificates they still have before the last day.
Sam Diego's ran two locations at one point. The Plymouth restaurant was sold to Jamie Suprenant, the son of one of the founders, and it's now an Añejo Mexican restaurant. In Hyannis, no buyer for the business came forward. In January 2025, the Cape Cod Times reported that the property and parking lot belong to a separate owner and weren't part of the sale. No plan for the site after the closing has been reported.
Since construction is due to start within weeks, the October events downtown are likely the last ones on the current one-way layout.
The Town's 2026 Hyannis schedule puts Restaurant Week at Oct. 15 to 21. A list of participating restaurants for this year hasn't been posted, so check before you book. Hyannis Open Streets follows on Sunday, Oct. 18, from noon to 4 p.m., with Oct. 25 as the rain date. The event closes the street to cars so people can walk, bike, dance, and socialize. For the May event, the Cape Cod Times described the closure as running along Main Street from Barnstable Road to Sea Street. The organizers haven't posted the fall schedule yet.
Main Street has gained at least one new spot this year. Summer House Cafe opened at 302 Main St. in the old Bread + Roses space. It serves all-day breakfast and specialty coffee, and its posted hours are 7 a.m. to 5 p.m. daily.
Changes like these, a lease that doesn't renew on Osterville's Main Street or a Route 132 building that goes dark, often lead owners to ask what their own property is worth before the new pattern settles in. If you own near Osterville's village center or downtown Hyannis and want a starting number while Great Streets gets underway, Tara Franklin can help, starting with your instant home valuation.
Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact us today.