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Osterville Fall Festival 2026: Fall Fun in Osterville, Cape Cod

🍁 Fall is the perfect time to visit Osterville! The Osterville Fall Festival returns to Osterville Village on Saturday, October 10, 2026, during Columbus Day Weekend. This family-friendly Cape Cod fall event is a fun way to enjoy the season with food, live music, shopping, local businesses, a dog parade, scarecrow displays, and activities for all ages.

Whether you’re looking for things to do on Cape Cod in October, a family-friendly fall activity, or a fun Columbus Day Weekend event, head to Osterville for a day of autumn fun in one of Cape Cod’s charming villages.  Bring the kids to this fun family Cape Cod Event. 

🍂 Osterville Fall Festival 2026

📅 Date: Saturday, October 10, 2026
📍 Location: Osterville Village, Osterville, MA
👨‍👩‍👧‍👦 Family-friendly: Yes — and dogs are welcome to join the fun!

🐾 Dog Parade – 11:00 AM

Bring your four-legged friend and dress them up for the Osterville Fall Festival Dog Parade! The parade begins at the Osterville Village Library and continues through the village. There will be prizes and treats for some of the best-dressed pups.

Weather permitting.

🍔 Food Trucks

Come hungry! Three food trucks will be serving up food and drinks throughout the day, including:

• 🍔 Mom & Pop’s Burgers
• 🍖 BBQ
• 🥤 Dirty Soda

🎨 Face Painting – 11:00 AM–2:30 PM

Kids can get into the fall festival spirit with face painting from Glitter & Gore.

🎶 Live Music

Enjoy live music throughout the day from Bill Hardy & Beth Sweeney while exploring Osterville Village.

💃 Line Dancing – 1:00 PM

Grab your boots and head to the Osterville Village Library lawn for line dancing with Kim from Bootlegging Line Dancing.

🍁 More Fall Fun Throughout Osterville

The fun doesn’t stop at the scheduled activities! Take a stroll through Osterville Village and check out local shops and businesses offering special sales, giveaways, treats, and surprises throughout the festival.

Be sure to look for the creative scarecrow displays created by local landscapers and Osterville businesses. It’s a fun way to explore the village while enjoying the beautiful fall scenery.

From shopping and food to music, dancing and a dog parade, the Osterville Fall Festival is a great way to spend a fall Saturday on Cape Cod.

🍂 Grab the family, bring the dog, and come fall in love with Osterville!

Looking for more Cape Cod fall events? Check out our guide to the best things to do on Cape Cod in October, including fall festivals, pumpkin picking, Halloween events, and family activities.