Things To Do
Restaurant Recommendations
Five Bays Bistro – A beloved Osterville staple offering slightly elevated American cuisine in a warm, inviting atmosphere; we even celebrated there after we got engaged! Chart Room at Crosby's - Located on the pier in Osterville, great for enjoying fresh seafood, a drink on the water, and beautiful harbor views. Pizza Barbone – A lively spot in Hyannis serving authentic Neapolitan-style pizzas with fresh ingredients and a fun, casual vibe perfect for a relaxed meal. Other Breakfast & Coffee Spots - Fig Tree Cafe (American diner), Nirvana Coffee Co.
Local Shopping and Activities
The 1856 Country Store: A trip to Osterville wouldn't be complete without a stop at the country store. Inside you’ll find a delightful mix of penny candy in jars, vintage toys, Cape Cod–themed souvenirs, cozy home décor, handmade soaps, scented candles, jams and jellies — plus fun, unexpected treasures that make browsing feel like stepping back in time Osterville Village Shops: Main Street is full of charming shops to explore, from small boutiques to coastal décor stores. Dowses Beach: A peaceful spot perfect for a crisp October day, where you can enjoy scenic walks along the shoreline and take in the ocean view. This is also where Justin proposed, 41.6229266, -70.3649130! Antique Shopping on Route 6A: If you love browsing for antiques, take a scenic drive along Route 6A and explore the many charming shops that line this beautiful stretch. A few of our favorites are Parnassus Book Service, Wayne’s Antiques, and (if you ventured that far) the Brewster General Store.