Located on the Rappahannock River with the open waters of Chesapeake Bay a few nautical miles away, Urbanna, Virginia, has more boats than people, according to locals. During the Urbanna Cup Regatta in spring, captains of all ages and skills gather at the Town Marina to race wooden 8-foot Cocktail Class Runabouts.
Planning a visit? Stay at Bethpage Camp-Resort.
The party is on the streets in November when the Official Oyster Festival of the Commonwealth shuts the town down for two days. The family fun features oyster-inspired art, the centerpiece parade with beauty queens and their courts from around Virginia and the hotly contested Oyster Shucking Contest.
Up the hill is the original Middlesex County courthouse, one of only 11 colonial houses of justice still standing in Virginia. Several neighboring buildings have been in continuous use since before the Revolution. Trollies ferry guests around the tidewater town that includes two public parks.