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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.

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.

He lives in Annapolis with his emotional support spouse, Louise White, and their rescue retriever, Millie.

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

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.

Wednesday, October 29, 2025

Celebrate National Cat Day: 1st Annual Caterwaul

Bay Ridge Wine & Spirits Tasting Room
111 Hillsmere Drive, Annapolis

6-8 pm

Presentation of 20 Cat Poems by 20 Cool Cat Poets presented by the
Poet Laureate of Annapolis, Jefferson Holland. Light refreshments and
wine tasting. A $10 donation is requested to benefit the SPCA of Anne
Arundel County.

Thursday, December 11, 2025

Top 10 Parks for Healthful Walks

Eastport/Annapolis Neck Library

269 Hillsmere Drive

Annapolis
6 - 7 pm

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.

Past Events

2025

September 25 - Private program, Governor Robert Bowie Chapter of the National Society of the Daughters of the American Revolution, Belair Mansion, Bowie, Maryland
August 21 - Dog Days Doggerel poetry challenge
July 13 - Celebration of the arts at the Mitchell Art Museum at St. John’s College
June 23 - Lothian Ruritan Club
May 27 - Historic Annapolis online lecture
May 18 - Concert at Heritage Harbour
May 17 - Lister Society
May 16 - Benefit concert at Chesapeake Region Accessible Boating
May 3 - Annapolis Book Festival at Key School
April 26 - History hike with Penn State alumni
April 26 - Earth Day celebration at St. Luke’s Church, Annapolis
April 22 - Eastport Yacht Club
April 18 - Recitation of “Paul Revere’s Ride” for historic re-enactment event, Maryland State House
April 6 - Guest performance at the Naptown Philharmonic Orchestra’s Earth Day Concert at Maryland Hall for the Creative Arts
April 4 - Gongshi Poetry Challenge at the Mitchell Art Museum at St. John’s College
March 27 - New electric bus launch at Pip Moyer Recreation Center
March 25 - Historic Annapolis zoom lecture
March 25 - Annapolis Rotary Club (breakfast meeting)
March 21 - Sock burning at Horn Point Harbor
March 10 - Anne Arundel County Chapter American Association of University Women
March 3 - Annapolis History Consortium, Maryland State Archives

2024

December 13 - "Poet Tree" program at Anne Arundel Community College
December 5 - Annapolis Mayor's holiday reception in City Council chambers, Annapolis
November 21 - Annapolis Rotary Club
November 19 - Parole Rotary Club
November 12 - Annapolis City Council Meeting, appointed Poet Laureate of Annapolis
October 12 - Anne Arundel County Recreation & Parks program
September - Wooden Boat Festival, Port Townsend, Washington
February - FisherPoets Gathering, Astoria, Oregon
March 20 - Sock burning at Horn Point Harbor, Annapolis
March 1 - Watershed Stewards Academy Conference, Maritime Conference Center
February 6 - PAX Conference at Patuxent Research Center
January 25 - Chesapeake Children's Museum
January 21 - Annapolis Rotary Club (evening meeting)
January 16 - Annapolis Maritime Museum
January 13 - Deale Historical Society

2023

November 8 - Green Drinks presentation, Annapolis
September 10 - Floating concert at Shaw Bay, Wye River
June 12 - West River Center, children’s program
March 21 - Sock burning at Horn Point Harbor, Annapolis
February - FisherPoets Gathering, Astoria, Oregon

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.
TO BUY: Please send a text to the author at 443-758-7797 so he can take your payment information and sign and dedicate the book to you or the person of your choice.

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.

TO BUY: Please send a text to the author at 443-758-7797 so he can take your payment information and sign and dedicate the book to you or the person of your choice.

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.

TO BUY: Please send a text to the author at 443-758-7797 so he can take your payment information and sign and dedicate the book to you or the person of your choice.

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!”

My Writer's Portfolio

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

​Jefferson Holland