​Jefferson Holland
Chesapeake Troubadour & Poet Laureate of Annapolis
Presenting concerts & programs
celebrating the Chesapeake Bay's natural history
& cultural heritage through original songs, stories & poems.
About Jefferson
Jefferson Holland, Poet Laureate of the City of Annapolis, is a modern-day Chesapeake Troubadour: singer, songwriter, poet, storyteller, performing all original material inspired by decades of life on the Bay.
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Jeff served as the director of the Annapolis Maritime Museum and the Riverkeeper for the West and Rhode Rivers. He co-founded the Chesapeake folk group “Crab Alley” in the 1980s and 90s and founded “Them Eastport Oyster Boys” with partner Kevin Brooks in 1992.
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He lives in Annapolis with his emotional support spouse, Louise White, and their rescue retriever, Millie.
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Jeff has released a collection of the outdoors columns that appear in the Annapolis Capital newspaper. Published by New Bay Books, it’s called “Walk Around Arundel: 52 places to hike with your dog (and other best friends).”
In 1980, I saw a documentary of Tom Wisner sitting at City Dock, playing his guitar and singing about the Bay, and I decided that’s who I wanted to be when I grew up.
Programs
Jeff brings a humorous flair to any program or event, combining stories, songs and poems with an Annapolis and Chesapeake Bay theme. He’s presented at meetings of civic organizations like the Rotary Club, the Ruritans and Optimists, performed at retirement communities, conferences and concerts in venues from Annapolis, Maryland to Astoria, Oregon.
His concerts and school programs celebrate the Chesapeake Bay's natural history and cultural heritage through original songs, stories and poems.
Presentations can be custom-crafted to any length from 20 to 90 minutes to suit the timeframe of your event and can be styled for any audience from toddlers to families to seasoned citizens. Here are some suggestions:
The Key to Annapolis History: A Poet’s Ode to Maryland
Jefferson Holland shares original epic poems and songs of the characters, events – and especially the traditional vessels – that make the capital of Maryland such an inspirational place.
Walk Around Arundel: 52 places to hike with your dog (and other best friends)
Jefferson Holland will share some of his favorite places to explore in Annapolis and Anne Arundel County with notes from his book, Walk Around Arundel: 52 places to hike with your dog (and other best friends) – a collection of essays from his popular column in the Annapolis Capital.
Tall Tales of Annapolis & the Chesapeake Bay – Despicable Pirates, 3,000-Year-Old Oyster Shells & Cannibal Crabs!
Storyteller Jefferson Holland presents a delightful program of original tall tales and songs inspired by the people and places of the Bay, from the Native Americans who feasted on oysters along her shores to the modern-day sailors who ply her waters.
Chessie: the Sea Monster that Ate Annapolis
All toddlers to tweens will enjoy Jefferson Holland’s delightful tale of a legendary beast who turns out to be a loveable 42-ton Chesapeake Bay retriever puppy. The story touches on themes of the cultural heritage of the Bay’s watermen as well as the natural history of the Bay’s critters.
Schedule
Saturday, September 6, 2025
Shaw Bay Rendezvous Floating Concert
Mouth of the Wye River
3 pm
Thursday, September 25, 2025
Private program
Governor Robert Bowie Chapter
National Society of the Daughters of the American Revolution
Belair Mansion, Bowie, Maryland
Tuesday, October 7, 2025
Historic Annapolis Virtual Lecture:
"Despicable Pirates, 3,000-Year-Old Oyster Shells & Cannibal Crabs!
Tall Tales of Annapolis & the Chesapeake Bay"
7 pm
Story teller Jefferson Holland presents a delightful program of original tall tales and songs inspired by the people and places of the Bay, from the Native Americans who feasted on oysters along her shores to the modern-day sailors who ply her waters. More info and to register.
Thursday, Dec. 11, 2025
Top 10 Parks for Healthful Walks
Eastport/Annapolis Neck Library
269 Hillsmere Drive
Annapolis
6 - 7 pm
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Author and Annapolis Poet Laureate Jefferson Holland reveals his top 10 parks for healthful walks with dogs (and other best friends) from his popular book by the same name.
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Books
Walk Around Arundel: 52 places to hike with your dog (and other best friends)
To wilderness guru John Muir, the forest was a temple, and he advised that we "saunter" through it with reverence. No hiking, thank you.
Walk Around Anne Arundel is a collection of newspaper columns inspired by sauntering through parks in and around Anne Arundel County with a good dog and a good friend or two.
In it, you'll make twofold discoveries. First, you'll visit nearby forests, Bayside beaches and riverside trails-all in a short drive from Annapolis and many nearly forgotten gems.
While reading-and sauntering-along with a dog-loving poet and storyteller, author Jefferson Holland, you'll also learn about the natural history and cultural heritage of each site.
$27.50 + tax & shipping. Paperback, 360 pages. Published by New Bay Books, 2024.
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Chessie, the Sea Monster that Ate Annapolis
Illustrated by Marcy Dunn Ramsay, this delightful children’s book tells the story in Suess-inspired verse of Captain Dan, the waterman, whose crab pot snags a mysterious, legendary beast that turns out to be a loveable 42-ton Chesapeake Bay retriever pup.
The story and the pictures touch on themes of the cultural heritage of the Bay’s watermen as well as the natural history of the Bay’s critters.
$20 + tax & shipping. Hardback, 32 pages. Published by Royal Oak Press,1994.
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Annapolis Verses Jefferson Holland
A collection of poems and tall tales of the Bay as presented to the audiences at the FisherPoets Gathering in Astoria, Oregon.
$10 + tax & shipping. Paperback chapbook, 32 pages. Published by Holland Lines, 2023.​​​
Poems
The Key to Annapolis History
Blood of the Bold Picaroon
Letter to the Editor
Ode to Rachel Carson
An Annapolis Christmas, 1783
Ben Ogle’s Bones
Eastport Parade of Lights
For the Young Poets of Annapolis
Muskrat Greene
Ode to the Equinox
The Viral Isolationist
Walkity Walk (a doggerel)
Here’s the way to save to Bay,
So it doesn’t get paved all over
Let’s get to work with a knife and fork --
And eat all the de-vel-opers
They can’t proliferate on a dinner plate
If you can’t beat ‘em, eat ‘em
Stories
The Waterman’s Outhouse
The Little Crab that Got Away
The Genie of Eastport
An Annapolis Boat Show VIP
“Praise the Lord!”
I wanna catch a blue crab in my net
As ospreys circle overhead
While paddling upon a quiet creek
And hear the geese a-swarming o’er
The marshes of the Eastern Shore
And see the skipjacks sail the Chesapeake
Songs
Anna's Song
Dining Aboard the Schooner Kathryn B
I’m a Man
Annapolis Shuffle
Do Do It
Back Creek Crab*
If You Can’t Beat ‘Em*
It Matters to This One
McNasby’s Oysters Jingle
Miss Lonesome*
SAV Tango*
Oyster Shells
Plastics Song
Shampoo
That’s My Maryland*
*sheet music is available
A Very Necessary Estuary
The only difference between a poem and the lyrics of a song is that one comes with a tune and the other one doesn't.
Video
That’s My Maryland
Maryland Public Television
with the Oyster Boys
Sieze the Bay
333 Coffee House
FisherPoets Gathering 2024
FisherPoets Gathering 2023
Audio
