Annapolis, MD, Guide and Information

Chesapeake anglers excited about the start of the rockfish season can enjoy their favorite sport and support three great causes by entering the Annual Boatyard Bar & Grill Opening Day “Catch & Release” Rockfish Tournament.

Participating fisherman not only compete for great prizes, they also give back to the Bay and their community since proceeds from the tournament benefit the Chesapeake Bay Foundation®, the Coastal Conservation Association Maryland and the Annapolis Police Foundation's Youth Fishing Camp. By enjoying a day on the water with friends and a fun party, they assist CBF with their “Save the Bay” efforts, help the CCA-MD protect the fishery, and introduce local kids-at-risk to Chesapeake fishing through The Annapolis Police Foundation’s Youth Fishing Camp – these kids establish long-lasting bonds with Annapolis police officers at the camp, a two-week program created by the late Lt. Brian Della.

The Annapolis Pride Parade is an annual event held in the city of Annapolis, Maryland, to celebrate the LGBTQ+ community and promote equality, diversity, and inclusion. The parade brings together people from all walks of life to celebrate the beauty and diversity of the LGBTQ+ community in a joyous and colorful event.

The first Annapolis Pride Parade was held in 2019 and has since become a much-awaited event in the city's calendar. The parade is organized by the Annapolis Pride organization, a nonprofit dedicated to creating a welcoming and inclusive environment for the LGBTQ+ community in Annapolis and surrounding areas.

As one of the premier boating events on the East Coast, the Annapolis Power Boat Show is a highly anticipated gathering of boating enthusiasts and industry professionals from around the world. This annual event, scheduled to take place in October, is a four-day celebration of all things boating, featuring the latest and greatest in powerboats, electronics, engines, and accessories.

The Annapolis Power Boat Show will be held at the City Dock in Annapolis, Maryland, a beautiful waterfront location that provides the perfect backdrop for this exciting event. Attendees can expect to see over 500 powerboats on display, including cruisers, sport fishing boats, center consoles, and more, all from top manufacturers in the boating industry.

From land and water, the Old World charm of Annapolis, Maryland enchants visitors and locals alike. If you wander through its rabbit warren maze of city streets, you will surely feel as though you’re walking through eighteenth-century America. Indeed, the red-brick buildings throughout Annapolis, most of which is classified as a National Historic District, present some of the finest examples of Colonial architecture in the country. Best of all, these small row houses (and of course some big mansions!) as well as their slivers of gardens and courtyards have been beautifully preserved; and as you approach the waterfront, many boast a lively scene peppered with beloved taverns, restaurants and shops.

Known as “America’s Sailing Capital” and also the “Sailing Capital of the World,” Annapolis, Maryland is best experienced from both land and water.

Have you ever taken a sail on the Chesapeake Bay? It’s an exhilarating experience punctuated by a flotilla of interesting sights, sounds and sensations both from the shore and the bay. Whether you’re taking a sail with Annapolis Sailing Cruises or motoring along in your own boat, time spent on the bay will allow you to fully appreciate how and why Annapolis became such an important maritime destination centuries ago. It will also help you to understand why that standing has endured in today’s world of modern tourism and travel.