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All Roads Lead to Osterville

Cape Cod Life  /  September/October 2023 /

Writer: Allyson Plessner / Photographer: Lane Caroline Photography 


What’s a classic Cape Cod wedding without a local band, a clambake, and a venue with some unique history? Shaun and Maddie Gross met in Philadelphia—mutual friends, a birthday party, and the rest is history. They got engaged on a romantic weekend away in New Hampshire, “I’m usually the planner,” laughs Maddie. “So I put a bug in his ear to plan a weekend trip, and he ran with it!” They spent three months together on a cross-country road trip, visiting national parks and sleeping in a rooftop tent. And, through all these memorable moments in so many incredible places, they eventually found themselves back in Osterville where Maddie grew up for a special day and the start of a life together.  “I always dreamed of getting married in Osterville,” reminisces Maddie. “Little did Shaun know,” she laughs. After returning from their epic road trip, the couple knew that Osterville wasn’t only the right place for them to get married; it was also where they wanted to build their lives together. They moved to the Cape full time in 2021 and got to work on planning the big day in a village they love so dearly. “It was important to us to showcase what a special place Osterville is to our friends and family,” says Maddie. Plus, with 25 first cousins, hosting a wedding close to home and family had a certain appeal. The couple decided on the Osterville Historical Museum as a venue for its “laid-back, classic Cape,” feel. “We also knew how much people would enjoy touring the historical boat shops during the cocktail hour,” adds Maddie. When planning, Shaun and Maddie were determined to ensure a few important details: a great band, flowing drinks, and a focus on local charm. “It was important to us to involve…


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Allyson Plessner

Allyson Plessner is a former editorial intern for Cape Cod Life and now works for the publication as a staff writer and digital media coordinator. Born in Florida, Allyson has been a lifelong summer resident of the Cape. She is a recent alumna of the College of Charleston, located in Charleston, South Carolina, where she completed bachelor’s degrees in both English and Spanish. In her free time, Allyson is an avid sailor, beach-goer, and—like her fellow Cape Cod Life colleagues—a dog-lover.