History Monday Sunset Sails

Historic Annapolis Skyline when sailing on Schooner WoodwindSunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind.

The Woodwinds features a History-slanted sunset sail every Monday night. When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.

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Schedule for  History Mondays 2016:

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capital WoodwindMonday, August 1: The Bay’s Environmental History: 1600-Present, Jennifer Miller Herzog 6:30-8:30

Join us for a discussion focused on the environmental history of the Chesapeake. This history lesson is a veritable “what to know” about past, present, and future impact of the relationship between the Bay’s land use and clean water.



Jennifer joined Chesapeake Bay Foundation in 2014 and is responsible for developing grassroots advocacy strategy and outreach activities to advance CBF’s policy priorities in Maryland. She works with our members, advocates, and Clean Water Captains to engage them during Maryland’s legislative session, develops and implements programs to involve citizens in issues and policy decisions affecting the Bay and their local waters, and builds partnerships with local organizations and groups.

She holds an MA from UNC-Chapel Hill and a BA from Hobart and William Smith Colleges. Returning to the East Coast and the Chesapeake Bay region after 15 years in Montana, she enjoys lots of time on the water paddleboarding, sailing with her family, and rowing with the Annapolis Rowing Club. 

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Jane Cox

Jane Cox

Monday, August 8: “Providence”: The  17th Century Town before Annapolis, Jane Cox  6:30-8:30

Jane will share the story of the colonial town that came before Annapolis. Providence was settled in 1649 along the shores of the Severn River and Whitehall Bay by a  group of Puritans who were seeking religious freedom. Jane has excavated seven archaeological sites that offer the last vestiges of this long forgotten period in Annapolis history, and will share stories of the sites, and the people who lived on them during the cruise. 

 C. Jane Cox is the Chief of Cultural Resources for Anne Arundel County. A native of Anne Arundel County and a graduate of the University of Maryland, she has worked as a preservationist and archaeologist for more than 20 years. She has excavated or studied over 200 archaeological sites in the County, including Providence- the topic of this lecture, and the seaport of Londontown on the South River. She has also spoken and published extensively on the 17th century origins of the County and City. She is also a founding member of the Lost Towns Project, a non-profit dedicated to the academic study of local history, and sharing that information with the public. www.losttownsproject.org 

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pirateMonday, August 15: Pirates of the Chesapeake, Heather Ersts  6:30-8:30

Pirates have plied the waters of the Chesapeake Bay for hundreds of years, and still do today. Hear tales of Black Beard, the town dubbed the “Nest of Pirates,” and today’s modern pirates as you sail along the same waterways they have sailed. 

 Heather Ersts is a public historian who specializes in heritage education, interpretation and programming.  She most enjoys connecting the public with historic sites and organizations through engaging programs that educate, inspire, and motivate people to get more involved in history.  She has work in a variety of museums and historical organizations.

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Monday, August 22: Legends and Lore of the Annapolis Waterfront, Dave Gendell  6:30-8:30


Dave Gendell brings aboard an entertaining and compelling set of stories and insights around Annapolis history, the Naval Academy, the sailing scene, and the personalities that make Annapolis one of the world’s most unique waterfront communities.

 Lifelong Annapolis sailor Dave Gendell is the co-founder of SpinSheet Magazine.

David Gendell

Dave Gendell

He has researched, written, and presented extensively on Annapolis and Chesapeake Bay history with a special focus on the Schooner AMERICA, World War II along the Annapolis waterfront, and the Thomas Point Lighthouse.

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Monday, August 29: Eating, Drinking and Making Merry in Colonial Annapolis, Diane Rey  5:30-7:30

Set sail with Anne Catharine Green, Annapolis’ 18th century Printer to the Province — a woman far ahead of her time — to discover the kinds of activities that helped make Annapolis the “Athens of America” during its golden age. Learn about early tavern life, sought-after imports, the “clubbical behavior” of the celebrated Tuesday Club, and the whirlwind that was Annapolis’ social season, as drawn from the pages of Mrs. Green’s newspaper, the Maryland Gazette. Enjoy your craft beer while hearing about the strange concoctions that Colonials quaffed! 

 Diane M. Rey portrays pioneering newspaper publisher Anne Catharine (Hoof) Green of Colonial Annapolis. A marketing professional and freelance writer, Diane has written a weekly community news column in The Capital newspaper that traces its history to the Maryland Gazette published by Mrs. Green in the run-up to the Revolution.

Diane Rey as Anne Catharine Green by Joshua McKerrow, Capital-Gazette

Diane Rey as Anne Catharine Green by Joshua McKerrow, Capital-Gazette

A lifelong Marylander who grew up on a large dairy farm in Frederick County, Diane traces her roots to the South River Hundred who settled in southern Anne Arundel County on the original land grants from Lord Baltimore.

She indulges her love of American history by bringing to life Mrs. Green who took over as official Printer to the Province of Maryland upon the death of her husband, Jonas Green, in 1767. Besides her work as editor, printer, and publisher of one of America’s first newspapers, Mrs. Green printed the laws, proceedings and paper money for the Maryland General Assembly after petitioning the legislature for the same contract extended to her husband  – 48,000 pounds of tobacco per year – making her an early example of “equal pay for equal work.” In 2010, this remarkable woman was inducted into the Maryland Women’s Hall of Fame. 

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Sunset over AnnapolisMonday, September 5: Navigation in the Colonial Chesapeake, Kyle Dalton   5:30-7:30

In the centuries before GPS, our ancestors relied on the stars, the horizon, and mathematics to find their way. Climb aboard and try your hand at using reproduced navigational instruments like the backstaff, traverse board, chip log, and cross staff. Learn about the value of latitude and longitude, and how our state was founded by men who braved the vast empty sea. 

 Beginning his career at the Maritime Museum of San Diego, Kyle Dalton is now the Public Programs Administrator and lead maritime interpreter for Historic London Town and Gardens in Edgewater, Maryland. He graduated summa cum laude from the Catholic University of America in 2014 majoring in History with a minor in Anthropology.

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The Eastport Flag

The Eastport Flag

Monday, September 12: The Maritime Republic of Eastport, Still revolting after all these years! Kevin Brooks 5:30-7:30

Join Eastport Oyster Boy and Local Revolutionary Kevin “Brother Shucker” Brooks for an entertaining look at the upstart “Maritime Republic of Eastport”‘s  interesting and down right fun history through the past four centuries. Historic forts, world class boat building centers, proud diversity, resilient waterman and becoming the ever fun and ever mighty Maritime Republic of Eastport!… Join Kevin for this fun, irreverent and music filled journey through the “Gulf of Eastport and Around the Horn”…(Horn Point that is…) sunset sail through history, music and mirth. 

 Sailor, musician, revolutionary and proud Eastportirican, Kevin is a founding member of the Eastport Oyster Boys.

kevin brooksWhen not performing with the boys can be found on his “good boat” the Pearl of Eastport cruising the waters of Gulf of Eastport and other exotic ports of call.

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 Monday, September 19: The Key to Annapolis History, Jefferson Holland 5:30-7:30

The Key to Annapolis history lies right there in the harbor;
It can’t be found by looking port; and it can’t by looking starboard;
It’s only when you drop the hook that the secret can be found:
When you anchor, you’ll discover that the bottom of the harbor is only 12 feet down!

Jeff serves as the Riverkeeper for the West and Rhode Rivers, estuaries just south of Annapolis.

Jeff Holland

Jeff Holland

He helped to launch the Annapolis Maritime Museum and was a founding member of Them Eastport Oyster Boys. He was appointed Poet Laureate of Eastport way back in the last century. “

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History Mondays with a little Fiddle Music (Tom Guay)

History Mondays with a little Fiddle Music (Tom Guay)

Monday, September 26: Tunes & Tales of the Golden Age of Annapolis, Tom Guay   5:30-7:30

Tunes & Tales of life during the Golden Age of Annapolis, the balls, the theater, the songs, the social season, which abruptly ended, forever, with the burning of the Peggy Stewart in 1774.

Tom Guay is a musicioner and young novelist who escaped Warshington (sic) DC, in 1999 with his wife, Karen, daughter, Elise, and son, Brendan, to enjoy life in Annapolis and the Land of Pleasant Living.

Tom plays fiddle, dulcimer and guitar in The Eastport Oyster Boys and is a veteran of several Irish folk groups, including the ShannonTide and Paddy Goes West.  With the Oyster Boys, Tom has written such literary wonders as “Hot Crabs, Cold Beer,” and “Pull, Pull, Pull,” an ode to the annual Tug-o-War between Eastport and Annapolis.

tom guay

Tom Guay

Tom is also a student of history, particularly colonial history. It’s no surprise then to see why he’s a docent at the Charles Carroll House here in Annapolis where he spins tales of the 18th century during the Golden Age of Annapolis, which ended abruptly with the burning of the Peggy Stewart in 1774.

All of these experiences turn up in Tom’s Tunes and Tales sessions on the Woodwind’s Monday evening history cruises. Ask him why about the “r” is in our first president’s name …

On fine fair days with a soft breeze, Tom can be found sailing coastal waters in his Tartan 27, The Salty Blue. When not performing or working on his novels, Tom works as communications director for the Severn River Association.  

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