This oyster-and-crab-rich island is also home to the famous Chincoteague ponies. While saltwater cowboys have been driving wild horses across the channel for auction since 1925, it was the children's book Misty of Chincoteague by Marguerite Henry that put the event, and this quiet little fishing town, on the map in 1947.
Today, tourism has replaced fishing as the primary industry in Chincoteague—more than 30,000 visitors pack the town on the last Wednesday and Thursday of July for the pony swim. Some of the best fun here is out on the water, whether crabbing or enjoying a richly detailed trip with Captain Dan's Tours to see the ponies, eagles, and other wildlife.
Restaurants such as Woody's Beach BBQ and Eatery keep the local catch in the spotlight with blue crab crabcakes and chowders, while duck decoy artists make the town a destination for collectors, who flock to Chincoteague Traders.
The 2,950 year-round residents have kept the area's small-town roots remarkably intact. Chincoteague has gussied up a bit since Misty's day, adding several new parks to its town center, including a brand-new expanse on the waterfront. That makes year-round life here all the happier.
Where to Stay: Perfectly suiting Chincoteague's small scale, the charming Channel Bass Inn offers eight distinctive rooms (some with lovely Chincoteague Bay views). And the property features English and Japanese gardens that are ideal spots for your morning cup of coffee. Rates start at $135; 757-336-6148 or channelbassinn.com.