Things To Do
Take a Selfie at Our Engagement Spot!
As you drive towards Oyster Harbors before you cross the bridge, there is a tiny little beach on Bridge Street. John LOVES the beach and stops here any chance he gets. This is where he proposed to Perry on a snowy day in January 2023!
Wimpy's Seafood Cafe & Market
We stop at Wimpy's every time we visit Osterville. John usually goes for the stuffed quahogs and a beer. Perry recommends the chowder and a Cape Codder!
Fancy's Market
Fancy's has pretty much everything you might need; a bottle of wine, a tooth brush, or a breakfast sandwich. It's worth stopping in just to walk around and see how much they've crammed into this local grocery store!
Spanky's Clam Shack and Seaside Saloon
Drawn in by the name after a ferry ride back from Nantucket, this became a new favorite for us in Hyannis. Partly a joke, we fell in love with the atmosphere, french fries, and John's joy for their lobster roll.
The Pineapple Caper Cafe
We never go here because the hours are weird but our family loves it! If you know Jay, you know it must be good to be his Osterville favorite!
Lilly Pulitzer
Perry says to go here if you have a wardrobe emergency!
Crisp
We love this pizza place it has so many great things on the menu besides pizza! Crisp Too has takeout and Crisp is a fun sit down place (they are located down the street from each other, Google Maps or Waze can get you there!) Both restaurants are very popular so the wait is long; plan accordingly!!