Nestled between the mainland and Assateague Island, Chincoteague Island is home to the largest community on the Eastern Shore and has on offer an array of water sports, seafood restaurants, a quaint little downtown and salty breezes. Chincoteague, the island's main town, is home to a permanent population of less than 4,500 though the stars of this Chesapeake swirled island are the semi-permanent residents of Assateague Island, the wild Chincoteague Ponies.
After years of isolation, Chincoteague was connected to the mainland by a causeway in 1922. Marguerite Henry's book" Misty of Chincoteague", published in 1947, introduced the world to the sleepy island's secret: the annual Pony Penning Day. Held every July since 1925 by the volunteer fire department, the penning centers around the wild ponies that are swum across the channel between Assateague to Chincoteague for a show and auction. The town fills to capacity for the annual event - if you plan to join the throngs, be sure to plan for a hike through the mud to get prime viewing spots at water's edge (and for more on the horse made famous by the book leave some time free to stop at Beebe Ranch, which has a mini-museum dedicated to Misty and her foal).
Island sights include Refuge Waterfowl Museum featuring hundreds of decoys, the Oyster & Maritime Museum housing the lens from the Assateague Island Lighthouse and the Island Aquarium, which explores life on the Chesapeake Bay.
Other options for recreation in the area include fishing, camping and tours to Assateague to spot wild ponies and birds. Be aware the wild ponies are not tame - if you're after a ride, the Pony Centre on Chincoteague offers rides and shows.
Chincoteague Island is located off the Eastern shore of Virginia, connected to the mainland and US 13 by Route 175, roughly two hours northeast of Norfolk up I-64.