FROM THE CHARMING brick‑lined streets populated with 18th‑century homes to the salty tang carried by the coastal breeze, the historic city of Annapolis is a memorable, year‑round destination for business and leisure. Located on Chesapeake Bay within Anne Arundel County — which offers some 520 miles of coastline — Annapolis has been connected to America’s history since the nation’s earliest days. It even served as the temporary U.S. capital from November 1783 until August 1784.
Annapolis’ rich history is a major draw, as is its role as a center of American sailing. The city is home to the United States Naval Academy, St. John’s College and the Maryland State House. Built in 1772 and notable as the site where the Treaty of Paris was ratified in 1784, the Maryland State House is the oldest state capitol in continuous legislative use in the United States. Its architecture features the largest wooden dome in America built entirely without nails.
Visitors also come to see historic gems like the Hammond‑Harwood House, which displays period furniture and paintings, and the Paca House and Garden, the Georgian mansion built by Declaration of Independence signer William Paca, known for its terraced Colonial‑style garden.
Weekly sailboat race at Annapolis Yacht Club © AMERICANSPIRIT | DREAMSTIME
“Tourism is a major player in the city’s economy, ranking second only to state government,” says Connie Del Signore, president and CEO of Visit Annapolis and Anne Arundel County. “Unlike many destinations, we are not seasonal. There’s something happening year‑round — even our sailing season lasts most of the year.”
The city’s annual calendar is full of events: boat shows, the Annapolis Film Festival, a winter lecture series at the Annapolis Maritime Museum, Restaurant Week in February, and a lineup of concerts, galas, theater performances, festivals and art fairs. Local quirks like the Annapolis Oyster Roast & Sock Burning add to the city’s character.
Popular activities include Wednesday night sailboat races and Saturday ArchiTrex tours that explore Annapolis’ architecture and stories in depth. In May the Chesapeake Bay Blues Festival draws music fans, and in June themed celebrations include the Greek, Italian and Irish festivals. The United States Naval Academy also presents a Distinguished Artist Series that features nationally and internationally recognized performers.
This broad event slate, combined with a scenic waterfront setting, makes Annapolis an attractive meetings and events destination. Besides downtown venues, meeting planners can choose locations near Baltimore‑Washington International Airport and the shopping and entertainment complex by Arundel Mills. These options increase appeal for delegates and often boost meeting attendance. From walking and food tours to sailing and special events, there is always something for attendees to enjoy.
Development projects continue to expand the area’s hospitality offerings. A notable example is the forthcoming flagship Live! Hotel at Maryland Live! Casino adjacent to Arundel Mills, a large property that will include guest rooms, dining options, spa facilities and a concert and events venue designed to host large gatherings.
SCENIC DRIVES
Annapolis and its surrounding region are steeped in history and natural beauty. Fort McHenry National Monument, the site tied to the Battle of Baltimore in 1814 and the inspiration for “The Star‑Spangled Banner,” lies less than an hour away and is easily accessed from I‑95. The park’s archaeology program has uncovered thousands of artifacts over decades, many on display in the site museum.
Within a two‑hour drive are dramatic outdoor destinations such as Cascade Falls in Patapsco Valley State Park and Great Falls Park on the Potomac River. Cascade Falls offers a 2.4‑mile loop trail with year‑round access. At Great Falls, the Potomac surges through Mather Gorge, creating scenic cascades and overlooks reached via established trails from the visitor center. Both areas are popular with hikers, birders and cyclists and provide memorable nature outings close to the city.