Legacy in Motion
2026-06-06 17:00 - 2026-07-11 17:00 (America/New_York) | MD
Launching Sail250:
Carrying Maryland’s Story to America
The wait is over. This weekend, Pride of Baltimore II officially kicks off her Sail250 season in Baltimore with the release of Case 1 Rum, a limited-edition collaboration with Old Line Spirits celebrating the beginning of a remarkable year for both the ship and our nation.
As America approaches its 250th anniversary, Pride of Baltimore II will spend the summer sailing alongside some of the world’s most iconic tall ships at official Sail250 events from Virginia to New York and Boston. As Maryland’s ambassador under sail, Pride will carry the story of the Chesapeake Bay and Baltimore’s maritime heritage to hundreds of thousands of visitors gathering to commemorate America’s semiquincentennial.
But this voyage is about more than the destinations. Through America’s Star-Spangled Ambassador: Legacy in Motion, a remarkable team of filmmakers, historians, journalists, educators, authors, students, and emerging media professionals will join portions of the voyage to document the experience and share it with audiences across the country.
The journey south to Virginia will feature documentary filmmaker Justin Black, maritime historian Andrew J. Lyter, and Towson University graduate Zoe H., capturing life aboard Pride and exploring the waterways and stories that helped shape America. The return voyage from Norfolk to Baltimore will include WYPR producer Mark Gunnery and apprentices from the Alexandria Seaport Foundation, highlighting both storytelling and maritime workforce development.
As Pride sails north to New York, acclaimed author and screenwriter Rafael Alvarez and public historian Kate Livie will bring their unique perspectives to the voyage, while aerial imagery will help capture the ship’s journey from a new vantage point. Continuing on to Boston, Stevenson University student Anjali J. will represent the next generation of storytellers, gaining hands-on experience documenting one of the nation’s most significant maritime commemorations.
Together, these participants will help tell Pride‘s Sail250 story through film, photography, writing, audio, social media, and educational programming—bringing audiences aboard the ship and connecting America’s past with its future.
Throughout the coming weeks, followers can expect a steady stream of stories, images, interviews, and behind-the-scenes perspectives from aboard Pride as she sails from Baltimore to Richmond, Norfolk, New York, Boston, and beyond.
Sail250 Voyage Schedule
June 12–14 | Richmond SailFest, Richmond, Virginia
June 19–23 | Sail250® Virginia, Norfolk, Virginia
June 24–30 | Sail250® Maryland & Airshow Baltimore, Baltimore, Maryland
July 3–7 | Sail4th250®, New York, New York
July 11–16 | Sail Boston®, Boston, Massachusetts
After completing her Sail250 voyage, Pride will continue her 39th sailing season with visits to Portland, Salem, Lunenburg, and Boston.
We invite you to follow along as Pride of Baltimore II carries Maryland’s maritime story to the nation during this historic celebration of America’s 250th anniversary.
Special thanks to the Baltimore Community Foundation for its generous support of America’s Star-Spangled Ambassador: Legacy in Motion.

Sailabration 2026
2026-09-26 10:00 - 15:00
SAILABRATION: SAILING TRADITIONS IN INK
Saturday, September 26, 2026 | 10 AM–3 PMBroadway Pier • Fell’s Point • FREE
Join Pride of Baltimore II on Broadway Pier for a one-of-a-kind waterfront celebration of sailors, stories, tattoos, music, and community. Held in historic Fell’s Point, where Baltimore’s privateers helped earn the city a reputation as a “nest of pirates,” Sailabration celebrates the traditions sailors carried across oceans through music, art, tattoos, and shared experiences.
Experience Baltimore’s maritime culture through live tattooing, music and performances, living history, hands-on activities, and family-friendly fun.
INK & SAILORS
Get Tattooed at Sailabration
The Baltimore Tattoo Museum returns with founder Chris Keaton, offering special souvenir tattoos of Pride II during the festival.

Choose from the artwork pictured here in black outline or full color. Tattoos are approximately 2.25″ H × 3″ L, take about 20 minutes, and range from $150–$200 depending on placement.
For more information and to reserve your spot contact Lori at Lori@pride2.org.
See Traditional Handpoke Tattooing

Before the electric tattoo machine was invented in 1891 by a former sailor, tattoos were made by hand, one poke at a time. Aboard ship, sailors used what they had on hand—including sail needles, India ink, laundry bluing, and even gunpowder.
Owen Payette McGarry, “Handpoke Tattooer,” demonstrates this traditional technique and explores its long connection to sailors and life at sea.
Explore the Stories Behind Sailor Tattoos

Maritime historian and author Andrew Lyter brings the world of early American sailors to life through stories of tattoos, traditions, and life at sea. Explore what sailors chose to ink on their bodies, what those symbols meant, and how tattooing became an enduring part of maritime culture.
STEP ABOARD PRIDE OF BALTIMORE II

Come aboard Baltimore’s world-traveling tall ship! Explore above and below decks, meet the crew, and discover what it takes to live and work aboard a traditional sailing vessel today.
Along the way, learn how Baltimore Clippers made their mark on history and how Pride of Baltimore II carries Baltimore’s maritime story to ports around the world.
Deck tours are free throughout the festival.
LIVE HISTORY & PERFORMANCE

Ms. Story’s Living History
Shemika Renee created Ms. Story’s Living History to honor the struggles and triumphs of Black women in history through first-person performance. Her portrayals introduce audiences to women whose lives helped shape their communities and the nation.
At Sailabration, meet a fascinating woman from Fell’s Point whose story influenced Baltimore’s sailing and waterways culture.

Society of the War of 1812 in Maryland Color Guard
Start the day with a bang! The Society of the War of 1812 in Maryland Color Guard brings the era of Baltimore’s privateers to life with a historic musket demonstration and a look at the weapons and military traditions of the War of 1812.

Frederick Douglass Comes to Life
Nathan M. Richardson, poet, author, and nationally acclaimed Frederick Douglass historian, brings one of America’s most influential voices to life through first-person interpretation.
Discover Douglass’s remarkable story and his deep connection to Baltimore, where his years along the waterfront helped shape the man who would become an abolitionist, writer, orator, and statesman.

Baltimore History with a Ukulele
Katie Long and her pal Bob Dietzen have been entertaining Baltimore audiences with ukulele parody songs for nearly 20 years. Their local-inspired tunes celebrate everything from the War of 1812 to Katie’s home base of Patterson Park, bringing Baltimore history and humor together with plenty of personality.

Ship’s Company Chanteymen
Hear the songs that once echoed across ships and waterfronts. Ship’s Company Chanteymen bring the music of 18th- and 19th-century sailors to life with work songs, sea chanteys, and tunes that helped crews keep time, work together, and pass the long hours at sea.

Shelby Blondell
Songwriter, singer, and advocate Shelby Blondell brings heartfelt storytelling and dynamic performances to Sailabration. Her music spans pop, rock, folk, and Christian, inspiring audiences with resilience, hope, and joy.
HANDS-ON FUN

Sailor Skills & Family Fun
There’s plenty for younger sailors to do at Sailabration! Stop by the Kidzone to make friendship bracelets, learn to tie sailor’s knots, test your skills with giant USA Jenga, and enjoy hands-on activities throughout the day.
Free activities for all ages.
EXPLORE MARITIME BALTIMORE & THE CHESAPEAKE

History MachineExplore the Star-Spangled Banner National Historic Trail.

Star-Spangled Banner Flag HouseDiscover the story behind the flag that inspired our national anthem.

Naval History and Heritage CommandExplore stories from more than two centuries of U.S. Navy history.

Historic Ships in BaltimoreDiscover Baltimore’s extraordinary collection of historic vessels.

Baltimore National Heritage AreaExplore the people, places, and stories that make Baltimore unique.

MDTA — Key Bridge RebuildSee what’s ahead for Baltimore’s new Key Bridge.
THANK YOU TO OUR SPONSORS
Sailabration is made possible through the generous support of our sponsors and community partners, helping us keep this one-of-a-kind waterfront festival free and open to all.

View Sponsorship Opportunities
