Special Events

Signature Events & Community Traditions in Osterville

There’s always something happening in beautiful Osterville Village, where community spirit meets seaside charm.

And now, with this new, beautifully redesigned website, residents and visitors alike can easily discover Osterville’s shops, restaurants, professionals, upcoming events and village news— all in one place.

Come experience the charm, community, and creativity that make Osterville one of Cape Cod’s most cherished villages.

Village Day

Held every third Saturday in July, Village Day is the heart of summer on Cape Cod. The morning begins with a scenic 5K road race winding through tree-lined streets and along the water, followed by the Village Parade featuring antique cars, floats, and family fun. Music, food, shopping, and smiling faces fill the day in a tradition that’s been celebrated for generations.

Business Connections & Learning

Throughout the year, the OBPA hosts educational workshops and networking sessions designed to help local businesses thrive. These sessions focus on marketing trends, digital strategy, and community collaboration, ensuring that Osterville’s business community remains vibrant and forward-thinking.

Fall Fest

Celebrate the season on Columbus Day weekend Saturday with a beloved autumn tradition. The day kicks off with a dog parade through the village, while shop windows are filled with creative scarecrow displays and fall décor. Families enjoy pumpkin patches, local vendors, and harvest treats in this picture-perfect Cape Cod experience that marks the start of sweater weather in style.