The island is accessible via a bridge from the mainland. The island has three communities, Deal Island, Chance, and Wenona. You get to Deal Island by taking Maryland Route 363 off Route 13 at Princess Anne and heading west. for about 15 miles.
Visitors will see watermen unloading the day’s catch, an oyster hatchery, and crab pickers at Deal Island Harbor on the northern tip of the island, just after crossing the Deal Island bridge. A public beach is also located in this area.
Each Labor Day weekend for the last 40 plus years, this island community has hosted the annual Deal Island Skipjack races. In addition to the skipjack races, this two day festival includes a crab skiff race, fishing contest, swimming contest, boat docking contest, a parade, amusement rides, arts and crafts booths, and food. The festival takes place at Deal Island Harbor. Bring a lawn chair and watch the race from the beach. The race takes place a ways off shore, so bring to binoculars to see the action. You can also launch kayaks from the sandy beach and paddle out for a closer view of the race.
The small harbor in Wenona is the home to several of the last remaining skipjacks on the Chesapeake Bay. These sailing ships still dredge for oysters in the winter. At the turn of the century, over 1,000 skipjacks worked the water. Now, only about 20 remain.
The Deal Island Wildlife Management Area is located on the mainland on the way out to Deal Island. This wildlife management area attracts many waterfowl, including many unusual varieties of ducks.
Pieceful Cottage Bed & Breakfast provides accomodations with beautiful waterfront views. The B&B is located in Wenona at the southern end of Deal Island. The B&B owner is a quilter who offers workshops and welcomes quilting a craft groups to the B&B.
Vacation home rentals are a nice way to enjoy Deal Island’s peaceful setting. See vacation rental listings.
August 30 – September 1, 2014. Deal Island Skpjack Race and Festival. The weekend-long event starts with a Gospel concert on Saturday. The skipjack race is on Monday morning. A parade, car show, fishing tournament, boat docking contest, and live music round out the weekend.
The Deal Island Skipjack Races. A schedule of events for the festival.
Deal Island/Chance Lions Club. Sponsor of the annual skipjack races.
Deal Island Wildlife Management Area. 13,000 acres of marsh and forest.
Somerset County Tourism Department. Information on activities, restaurants, and lodging.