View from the Chart Room at Crosby's

View from the Chart Room at Crosby’s. Photo by Lindsie Silvia

Osterville – By Blair Miller

In the quaint village of Osterville, it’s hard to miss the elegance that is woven into every bit of this community nestled along the southern side of Cape Cod facing Nantucket Sound. Whether it’s simply driving through as you head toward Dowses Beach or taking a stroll down Main Street, there’s a different feeling here. The charm and distinction exist beyond the boutiques or the well-manicured homes, which certainly help define the reputation that so many people have cherished for centuries.

To understand Osterville, you must know that its history is defined in its name that exists today simply by mistake, if you believe the tales of the past. Osterville’s history is just as impressive as many of its New England neighbors and dates back to the 1600s. Originally, the area was called Cotachessett but then became known as Oysterville, as a nod to the many people who came here to go oystering. Legend has it that over time, the “y” was dropped because people kept misspelling the original name. But there’s no mistaking the riches of the sea that this village has to offer.

The heart of this village runs right down Main Street, lined with classic shops, boutiques, restaurants and cafes. Many of these small businesses are family-owned and a staple of this community. In the heart of Osterville, Five Bays Bistro is a contemporary hotspot. The owners, Jamie Surprenant and Tim Souza, have been in the restaurant business for decades and wanted something you might find in a major city. Its American cuisine with modern flair, like the Apple Cider Brined Duck Breast with sweet potato and braised pork hash and pomegranate gastrique, exemplifies the unexpected and subtle sophistication that embues each dining experience.

A bit farther down Main Street, it is not uncommon to find a bustling crowd spilling out of the Pineapple Caper. Owners Tammy and Bill Russell changed their lives to open the café that started as a food truck and catering business. Bill left the corporate world last year to join his wife in the kitchen. Tammy has spent much of her life in the culinary field but wanted something more. Best known for its grilled cheese sandwiches on sourdough, the new brick-and-mortar offering has delivered the challenge Tammy envisioned, as well as a new popular destination for visitors.

Perhaps one of the best-known and most rooted restaurants in Osterville is Wimpy’s. What started as just a small hamburger joint in 1938 has grown into a beloved 200-seat establishment serving a variety of classic lunch and dinner fare. Just up the street from Wimpy’s is Fancy’s Market, a go-to for locals and visitors alike in search of prepared meals, deli fare, baked goods, fresh produce and an impressive wine selection.

Come spring, Amie Bakery will move to its new, larger flagship location farther up Main Street. This community hub will be the perfect place to start your morning—with a cup of coffee and, of course, one (or two or three) of the bakery’s irresistible artisan pastries.

When it comes to shopping, there’s something for everyone—whether it’s Island Outfitters, featuring quintessential Cape apparel, or Pocket Full of Posies, which carries unique clothing for children and offers in-house monogrammimg. Oyster Island Emporium is a treasure trove of fine nautical homewares and accessories—a perfect memento for your time in town.

Off the beaten path of Wianno Avenue, there’s the Chart Room at Crosby’s, the sister restaurant to the popular Chart Room in Cataumet. Open during the warmer months, diners can take in the beautiful waterfront views along North Bay, seated inside or outside.

The Osterville Historical Museum chronicles the town’s history. Director Jenn Williamson says Osterville’s story reflects the story of America. “In our case especially, it is all about the sea,” says Williamson. “As we approach the 400th anniversary of the Pilgrims landing on Cape Cod, we can trace back our early Osterville families to the very beginnings of this place we are lucky enough to call home.”

Williamson points to the family names that still hold weight around Osterville. “The Crosbys are America’s oldest currently active wooden boat-building family. For nine generations, the Crosbys have built boats on the bays of Osterville using a Colonial method of carving half-hull boat models. Even today, you can still see hundred-year-old Crosby catboats or Wianno Seniors sailing in Nantucket Sound on a warm summer afternoon.”

The museum hosts events all year, including the Village Day Antique Car Parade and the Art @ The Museum art show and sale. Part of their mission is being involved in the community, as evidenced by their popular Farmers’ Market, held each Friday from mid-June to mid-September. “Our farmers and small-batch food vendors are like none other. On any given Friday, we can bring in 600 to 800 visitors to the village,” says Williamson.

The summer months are full of events designed for people to enjoy the beauty of being outside and to attract visitors from beyond the village’s borders. But perhaps the most popular event is the Osterville Chocolate Festival, which is held in February. The festival’s popularity may be fueled by the samples that everyone can try for free after the judging.

Whether sampling chocolate in the winter, or sipping a mudslide on a hot August night at the Chart Room at Crosby’s, taking the time to pause in Osterville is a moment you will never regret.

On the next page, read about a few notable businesses that help make Barnstable special!