2024 Sailing Season is coming! See you April 13, 2024!

Battle of the Severn

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Learn the forgotten story of the lost town of “Providence”, the first Annapolis. The Battle of the Severn was a bloody skirmish fought on March 25, 1655, on the Severn River at Horn Point (today’s Eastport). It was an extension of the conflicts surrounding the English Civil War, pitting the forces of Puritan settlers against ... Read more

Buffets, Bands and Beaches – Socializing on the Severn

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Bay Ridge Resort was developed in 1879 as a grand Victorian summer resort with a large frame hotel on the bluff near Tolly Point. Weekends were filled with USNA bands, lawn games, live animals, and frivolilties for those wealthy enough to come by ferry or rail. In the mid-1900s, Carr and Sparrow beaches were the ... Read more

History of Watermen on the Chesapeake

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Annapolis is known as a Seafood hub on the east coast. Most people love their Crabs and Oysters, but how many people know where their seafood comes from and how it is caught? Annapolis has been the center of the seafood industry on the Chesapeake, ride along to hear the history of Seafood and Watermen ... Read more

The War of 1812 on the Chesapeake

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

The War of 1812 is considered the Second American Revolution and Maryland played a pivotal role in the conflict. Hear stories of the bold privateers that wreaked havoc on the British Merchant Fleet, numerous clashes along the shores of the Chesapeake Bay, and learn how brave Marylanders defended their homes and inspired a nation! History ... Read more

On the Horizon – Annapolis Landmarks Seen from the Water

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Four iconic buildings and areas on the Annapolis waterfront and skyline will be discussed and their historical importance: the Maryland State House, the USNA Chapel, St. Mary's Church, and the Annapolis Harbor and waterfront. There's a reason the city retains its colonial appeal and charm and much of it is tied to these four. History ... Read more

Sediment and the Chesapeake

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sediment is an important component of the Chesapeake Bay ecosystem. Often viewed as a pollutant due to its impact on water clarity and potential to settle on bottom dwelling flora and fauna, sediment also has positive aspects in the estuary. The talk will cover a range of sediment related topics focusing on sources (watershed, shore ... Read more

Bay Ridge Queen Resort of the Chesapeake

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

A detailed account of the turn-of-the-century decades when Bay Ridge flourished as a grand Victorian resort served by steamship and train. A narrated tour of a bygone era – brought to life through enlarged photographs. History Monday Sunset Sails occur every Monday, May-September 22. Different topics and speakers vary throughout the season. Our bar includes ... Read more

History of Shipping in the Chesapeake Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Ever since the colonists arrived here IN SHIPS, there has been shipping. Come discuss with us, the fascinating history and differences of early local maritime shipments and how drastically different things look today. History Monday Sunset Sails occur every Monday, May-September 22. Different topics and speakers vary throughout the season. Our bar includes a selection ... Read more

Greenbury Point – Towers to the Past

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

For over the course of two world wars and well beyond, the people of Annapolis played golf next to and boated past America’s most top-secret military communication facility and didn’t have a clue they were living near our nation’s first line of defense. On our sunset sail, we will unravel the guarded government secrets that ... Read more

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