Eastport Oyster Boys Musical Goodwill Ambassadors of the Chesapeake!

Eastport Oyster Boys Musical Goodwill Ambassadors of the Chesapeake!

Eastport Oyster Boys Musical Goodwill Ambassadors of the Chesapeake!Eastport Oyster Boys Musical Goodwill Ambassadors of the Chesapeake!Eastport Oyster Boys Musical Goodwill Ambassadors of the Chesapeake!

Check out our latest tour dates, music and upcoming events by clicking the 2020 Tour Dates button below!... Up The Republic!

About Us Boys.....


Modern Maritime Music Misfits

Modern Maritime Music Misfits

Modern Maritime Music Misfits

Appointed the Musical Goodwill Ambassadors by the City of Annapolis and the Maritime Republic of Eastport, the Eastport Oyster Boys love to share their musical celebration and stories of life on the shores of the Chesapeake Bay. For over two decades they have educated, amused and delighted thousands with their wit, wisdom and special message of stewardship and appreciation for the Bay and its unique maritime culture and history. The Oyster Boys’ simple philosophy is wrapped up in the three basic necessities of life “a good hat, a good dog and a good boat!.


Oyster Boy Music and Mirth

Modern Maritime Music Misfits

Modern Maritime Music Misfits


The Boys are a collaboration of four of the Chesapeake region’s finest and most experienced performers and bring with them a wide variety of instrumentation including acoustic/electric guitars, keyboards, banjo, fiddle, melodica, trombone and even hammered dulcimer. The Boys musical tastes cross numerous genres and include island rhythms, Americana, boogie, Celtic, dixie swing, chanteys, waltzes and even some good ol’ rock-and-roll. 


Inspired by all things Chesapeake~

Inspired by all things Chesapeake~

Inspired by all things Chesapeake~


The Eastport Oyster Boys are known for their engaging and interactive presence with audiences. Along with their original music and songs of the area, The Boys often engage in an abbreviated and sometimes ever so slightly modified history of the Bay, its unique culture and characters and allude to some inside anecdotes that oft times inspire The Oyster Boys’ material. Most of all, audiences will remember the good fun they had and will go home with a bit of the Chesapeake in their blood. 


Musical Goodwill Ambassadors

Inspired by all things Chesapeake~

Inspired by all things Chesapeake~


The Boys have traveled regionally as well as internationally as Musical Goodwill Ambassadors on behalf of the City of Annapolis, the Maritime Republic of Eastport and the Chesapeake...... 

Rise Up! We Are All In This Together!


The Eastport Oyster Boys preform a tribute song dedicated to the victims of the tragic shooting at the Capital Gazette on June 26. Rise Up! written by EOB's own Mike Lange piano/keyboardist. Filmed during rehearsal and in performance at Maryland Hall for the Creative Arts, July 2018. Special thanks to Backfin Media

What the Press is say'n about them boys...


  If you’ve lost sight of why you live here, it’s time you heard The Eastport Oyster Boys. With tongues planted firmly in their cheeks, they write and sing songs about laid-back life on the Bay. They mix droll wit and a veritable cornucopia of musical styles – from Cuban jazz to Dixie swing to rockabilly to waltzes to calypso to country weepers to tangos….and they do it all with a joie de vivre that fuels good times like high octane gasoline. -- The Washington Post

“When a former president comes to town, who do you call for fun? On a night in June, it was the Eastport Oyster Boys. The popular local band was tapped by Visit Annapolis to play June 23 at the Chesapeake Bay Beach Club on Kent Island, where former President Jimmy Carter was making an appearance with his wife, Rosalynn Carter, for a Carter Center retreat week. Former Vice President Walter Mondale was also in attendance, along with about 300 members and supporters of the Carter Center, 

Megan Brockett , The Capital 

“In a town where your sailing shoes are your dancing shoes, where your dog is welcome on the dance floor, and where the dance floor just may be the deck of your boat, the Eastport Oyster Boys sound like home”.

Molly Winans,  Managing Editor at SpinSheet Publishing Company

“The Eastport Oyster Boys truly embody the "Land of Pleasant Living" spirit in the their songs and live performance. They will surely get your toes a tappin', head a boppin', and soul a singin'! If you're looking for a fun evening, look no further! “

Robert Ferrier Emmy Award Winning Director, Writer, Producer, Executive Producer

“These are some of the most talented, creative and fun guys to ever entertain. Their music of life on the Chesapeake Bay, the Ditch and beyond will entertain and amuse you. Hard to choose three attributes, I'd check every one if the system would allow. Put them on your must see list in Annapolis or other parts of the Chesapeake Bay region, you won't be disappointed.”

Denise Mileski, Director, Business Development at The Coalition for Government Procurement

“It has never been a one- or two-man show. It’s been a team effort from the beginning, of recognizing, adapting, and using talents that are in our toolbox. That’s what worked.”  Everybody sings, tells jokes, laughs, and does whatever comes to mind. Often, there’s a guest musician or two sitting in—drummer, bass player (Pete Miller), tuba-player, or what have you. The music is organic, homegrown, pertinent, and it covers the gamut—boogie, island, Celtic, swing, chanteys, rock & roll, gospel, and Americana. And it works, judging by the festive herds who show up to dance and sing along, knowing every lyric. “The range of our music reflects the diversity of Chesapeake culture, its character and its characters,” says Brooks. 

Joe Evans, Senior Editor, Chesapeake Bay Magazine , November 2019



Upcoming Performances!!


Please contact us at or call 443 510 0831 for 2020 booking information and pricing..... Thanks

The Eastport Oyster Boys provide a truly unique, original, fun filled Chesapeake infused music and mirth for your group or event during your visit to the our home waters. They are the perfect entertainment for groups large or small and offer several performance options to accommodate your event & audience. 

2020 Performance Options

The Oyster Boy 

Founding member of the Eastport Oyster Boys, Kevin “Brother Shucker” Brooks provides a fun, engaging and informative one man show on guitar and banjo sharing the laid back lifestyle in the Maritime Republic of Eastport, Annapolis and the Chesapeake in song and story. Kevin can tailor his performance to your group interests and time frame.

The EOB Duo 

The EOB Duo presents a fun, entertaining “musical history tour” of life along the shores of the Chesapeake, Historic Annapolis and the Maritime Republic of Eastport. Instrumentation includes acoustic/electric guitars, fiddle, banjo and hammered dulcimer. This musical performance and presentation is reserved for smaller groups and more intimate settings. 

The Eastport Oyster Boy Band 

The EOB Band brings to life the character of the Oyster Boys’ creative, one of a kind Chesapeake Bay sound and is perfect for larger groups, festivals, conference and both indoor and outdoor settings. This is the boy’s standard four-five piece configuration and works well for larger groups and spaces and offers a vast array of musical styles and dynamics.  Instrumentation can include: keyboard, electric/acoustic guitars, bass, fiddle, banjo, trombone/trumpet, uke, hammered dulcimer and melodica.

Non Profit Partnership Rate: For pricing information on The Eastport Oyster Boy 2019 Non Profit Partnership rate for qualifying 501 c 3 organizations please contact us at

Note: All fees may vary depending on specifics pertaining to each performance.


Who are those guys?


Kevin Brooks Guitar, Six String Banjo

and Vocals

An avid sailor, songwriter and musician, Kevin brings a rich music heritage to the Oyster Boys having performed as bassist/vocalist with top regional folk artists including Mack Bailey, the Shannon Tide and other high energy folk and original groups. During Kevin's 30+ plus year career in music, he has shared the stage with such musical legends as Glenn Yarbourgh, Chet Atkins, The Wolfe Tones, Charlie Byrd and numerous regional, national and international talents. His song writing has filled a catalog of Oyster Boy hits including “Good Hat, Good Dog , Good Boat”,” Downy Ocean Hon”, “This Too Shall Pass” and several newly released songs for the boys. He has co-produced several CDs for the group as well as other local maritime music artists and has appeared on numerous recording projects. When not performing with the boys, he may be found “gunkholing” around the Chesapeake with his wife Jan on their 30’ Cape Dory Cutter “Pearl of Eastport”. He has performed at the Kennedy Center, Pier 6 and the Baltimore Arena as well as internationally (Ireland, Nova Scotia, Estonia) as a Musical Goodwill Ambassador of the City of Annapolis,

Tom Guay – Electric and acoustic guitars, fiddle and hammer dulcimer, vocals 

Tom hooked up with the EOBs after he escaped Warshington,(sic) DC in 1999 to come to the paradise we call Annapolis. He plays the traditional Celtic Stratocaster to add a bit of RnR flash. Tommy boy also sprinkles in Irish tunes on hammer dulcimer and fiddle to spice up the EOB stew.  Before joining EOBs, he played pedal steel guitar various bands during in the country rock heyday, switched to playing bass in the Irish folk groups and bass again in blues and rock bands and then switched to guitar when he co-founded the Fabulous Potato Heads Rhythm & Blues Ceili Band, the biggest (longest actually) name in Irish rock. Tom’s song writing styles reflect a strong folk and celtic influence and has penned several new Oyster Boy standards. Tom finds creativity aboard his 27’ Tartan “Salty Blue” and his fleet of small boats. When not on stage with the Oyster Boys, Tom is the Program Officer for the Severn River Assn helping to protect our valuable waterways.

Mike Lange - Keyboards, uke and melodica, vocals 

Mike is a well-known and respected keyboardist and singer song writer that has performed over a thousand gigs throughout the Mid Atlantic and overseas. He is best known for his outstanding swing and boogie woogie styles but is equally adept at song writing and arrangements. Mike has two self produced CD”s and has had ample airplay on major market radio in the Mid Atlantic. Mike along with his musical wife Kelly, is also an avid boater/cruiser and claims to be one of the few Bay boaters to cruise to the Bahamas… in a Boston Whaler from the Chesapeake!  Before Mike joined the Oyster Boys, he was best known for his own group Mike Lange and Boogie Express. Mike and Kelly Lange appear often around the harbor during the summer sailing season on the Schooner Woodwind and other popular venues.

Andrew “Captain Andy” Fegley - Trombone, percussion and vocals 

Andrew Fegley, local marine electrical business owner (Yacht Electronics Systems - YES), has been playing trombone with various Annapolis bands since the mid-1980s.  He studied music in college long enough to realize he would need to find an unusual outlet for his specific artistic talent. . . .and he found a home with the Eastport Oyster Boys since the mid 1990’s. Beyond his musical talents, Andy is an accomplished professional mariner with thousands of sea miles in his log book. He and his wife Amanda can be frequently found on their custom 40’ trawler “Yes” around the waters of Annapolis.

What folks are say'n about the boys....

 "One of the East Coast's most entertaining quartets "  Coe Sherrod, Woodstock Cafe, Woodstock, VA

 "In this time of cold and darkness, the Eastport Oyster Boys bring hope of a better time to come!! Thanks, guys! "

John W.


American Cruise Lines passenger “After our delicious dinner, we had a musical performance of “The Oyster Boys”. A fun musical duo from Annapolis where we will sailing to tomorrow. They were quite accomplished musicians of many instruments and gave us a informal education of Eastport and Annapolis. They said, “we are your first introduction to the area, so when you go on your tours and they try to tell you things different than we told you, you tell they are wrong that the Oysters Boys said.” They were quite funny and we gave them a standing ovation”. 

"Your music and overall entertainment was the are the true flavor of Annapolis". Adrienne M. (Corporate Conference)

"My sincere “Thanks!” to The Oyster Boys for the wonderful performance they provided for our conference. They certainly had those lawyers, judges and bar association executive directors singing and clapping their hands. Everyone had a great time listening to the music and learning about our very special area and way of life. As chair of the Host Committee of the MD State Bar Association, I’m very pleased with your assistance and the fine work of The Boys! We highly recommend the group to all visitors!" James N.

You really WOWED ‘em on Saturday night! It was really awesome having you entertain us. A fantastic journey through the region, in song, prose and jest – JUST PERFECT! A good time was had by all". S.K. (Private Party)

"I wanted to thank all of you for helping to make our Saturday evening banquet such a success…everyone had a great time…your choice of songs was so appropriate. Including some inside humor was great. I will recommend you to others for a fun, yet educational evening. Thanks again. I can tell you are special people, with your priorities in the right place!"Dottie A. (Organizational Meeting, Dinner Entertainment)

"It was wonderful to have you there to bring such fun to so many people! Your music was irresistible to the crowd and adds so much to our sense of history and place. Your songs of the region contributed greatly to the perfect atmosphere. We hope you will return. I don’t think we can have this event without you! Thank you, thank you, thank you!" Susan S. Oyster Roast

"I want to thank you for your contribution to the outstanding success of the Invitational held in Annapolis. Your performance at breakfast was certainly a highlight of the meeting. I absolutely fell in love with your music and it is so right and perfect for Annapolis and Maryland. Thank you so much for helping to make the Annapolis meeting one of our best ever". Stephen K. (Conference breakfast)

"These are some of the most talented, creative and fun guys to ever entertain. Their music of life on the Chesapeake Bay and beyond will entertain and amuse you. Put them on your must see list in Annapolis or other parts of the Chesapeake Bay region, you won't be disappointed". Denise M. 


Past Venues.... yup, we've been there....


Sampling of performances and venues we boys have been honored to share our music and mirth.....

Performance for President Jimmy Carter and the Carter Foundation, Annapolis, MD

Estonia Folk Life Music Festival, Viljandi, Estonia

Kinsale Jazz Fest, County Cork, Ireland (several musical tours of Ireland)

Prince Theater, Annapolis Royal, Nova Scotia

American Cruise Lines, Ship board entertainers, various port and vessels 

Maryland Hall for the Creative Arts, Annapolis, MD

Garfield Center for the Performing Arts, Chestertown, MD

Smithsonian Folk Life Festival, Washington DC

Avalon Theater & Stoltz Listening Room, Easton Maryland

Maryland Public Television, ARD German Television, BBC, Marine TV, CBC numerous international film and print media including the Washington Post, Annapolis Capital Gazette, Soundings, Chesapeake Bay Magazine, Spinsheet and many more.....

Chesapeake Bay Foundation/Oyster Recovery Partnership/ Chesapeake Bay Alliance various events

Benefits for the Pride of Baltimore II, Baltimore, MD

Clean Water Coalition, Baltimore, MD

Maryland Maritime Heritage Festival(s), Annapolis, MD

Great Baltimore Oyster Festival, Baltimore, MD

Woodstock Cafe Bay Days, Woodstock, VA

Maryland Fleet Week, Baltimore, MD

Historic London Town Public House, Edgewater, MD

Fort McHenry National Historic Monument, Baltimore, MD (various events)

Maryland Seafood Festival, Urbanna Oyster Festival, numerous regional events

Performance aboard Maryland Independence for the Chairman of the Joint Chiefs of Staff and NATO Dignitaries  

Maryland Governor’s Office of Tourism 

Annapolis Maritime Museum, 

Chesapeake Bay Museum, Calvert Marine Museum and more

Mariners Museum, Hampton, VA

Maryland State House, Annapolis, MD

Stanley Foundation, Washington DC

Maryland State Bar Association, Baltimore, MD

Rotary International National Conference, Washington, DC

National Conference for Speakers of the House, Baltimore, MD

Booze, Allen & Hamilton 

American Waters Resource Association, Baltimore, MD

American College of Physicians, Annapolis, MD

Association of Transportation Law Professionals

National Association of Secretaries of State

Association for Applied Anthropology

American Bus Association 

National Magazine Publishers 

Great Chefs of Europe US Tour, St. Michael's, MD

Too name a few……….phew.... 


Do the boys have a discounted rate for qualifying non profit and educational organizations...

YUP... ask about our 2020 Non Profit Partnership rates....

Will the Boys play at my private party/event at my home?

You Bet!!..Especially if we can come by water!

How long have the Boys been performing together? 

Gee.. 25 years and countin''s that?