The Best Ways to Experience Maryland in Chesapeake Bay
Sometimes little ol’ Maryland can be overshadowed by the vastness that Virginia has to offer those sailing through the Chesapeake Bay. These underrated points of interests that lie along the Chesapeake offer bareboat sailors much more than they bargained for.
Annapolis is the sailing mecca of the U.S. Every October it sees thousands make their pilgrimage to watch the sailboat and power boat shows. If you happen to be there on a Wednesday night you can see the weekly sailboat races that occur every Wednesday from May to early September. Admission is free to watch over 150 boats compete in this heated midweek competition. If you’re looking to bolster your knowledge of sailing, you or your little ones can take sailing lessons tailored to just about any type of sailboat. If you’ve got a bad case of sea legs, walk along Ego Alley to witness some of the most impressive boats the town has to offer sail up the narrow waterway.
Maryland’s only inhabited island unattached via bridge or causeway is just about as north as Maryland reaches. Here tourism varies, as the island is only accessible via boat. Once on the island you’ll find that golf carts and bicycles are the main means of transportation and are available for rent at a number of venues. Smith’s Island is the chief destination for those looking for a quiet getaway. The town’s cuisine, crab cake sandwiches and Smith Island cakes – packed with 10 layers of cake and icing- must be tasted by any reputable coastal gastronome. One of your first stops on the island should be the Smith Island Center which will provide you with an appreciation of the island as well as a proper introduction.
For the complete opposite experience of staying on the tranquil Smith Island, head south to Baltimore. During the War of 1812 the British referred to Feels Point as a “nest of pirates,” which still rings true today. This Baltimore neighborhood lays claim to one of the best nightlife atmospheres in the whole of the Chesapeake. 120 bars and restaurants are now the main source of commerce for a neighborhood that used to be one of the key boat manufacturing locales in the US. Along with sailboat production, one of Baltimore’s first key areas of industry was beer manufacturing. Dozens of breweries and brewpubs are now getting prepping for the annual Beer Week held in October in honour of Fells Point’s craft beer.
Maryland should no longer be playing second-mate to Virginia in the battle of Chesapeake Bay tourism. It offers an eclectic range of opportunities for any bareboat sailor looking for a bit of seafaring fun.