Cape Charles is a Sail Virginia℠ 2026 affiliate harbor and will host SailFest Cape Charles from June 19-21, 2026. Historic, featured vessels that will be in Cape Charles harbor include Kalmar Nyckel, Lynx, AJ Meerwald, and Luna.
Get ready to witness history as majestic tall ships sail into Cape Charles for SailFest Cape Charles! These historic vessels, along with beautifully restored Chesapeake Bay Oyster Buy Boats will give visitors a rare glimpse into the maritime heritage of Virginia’s Eastern Shore. Whether you’re a history lover or just looking for a unique experience, this festival is not to be missed!
SailFest Cape Charles will feature free ship tours of our visiting historic sailing vessels, period re-enactors, presentations by local historians, free hands-on activities for kids – including an opportunity to sail a sunfish with an instructor, fife & drum corps, music on the bandshell stage both afternoons and a Saturday evening concert featuring Three Sheets to the Wind, a curated vendors market, food, fireworks, and fun! All are welcome to enjoy this beautiful bayside setting while we celebrate the 250th anniversary of the founding of our nation!
More at https://sailfestcapecharles.com/
Here it is, the itinerary:
Saturday, June 20
12:00
Opening Ceremony
Alvie Powell, National Anthem
Top of ramp to docks
12:00 – 6:00
Ship Deck Tours
All Boats Open to Visitors
Docks
12:00 – 6:00
Kids Activities
Virginia Institute of Marine Science Touch Tank
12:00 – 6:00
Kids Activities
Virginia Navy Galley — Norfolk Revenge
Re-enactors Encampment · Harbor
12:00 – 3:00
Kids Activities
Northampton Bookmobile
12:00 – 4:00
Kids Activities
Cape Charles Community Sailing Experience
12:15 – 12:45
Music
Williamsburg Field Musick
Stroll on docks
12:30 – 4:30
Kids Activities
Face Painting with Emily’s Fun Faces
12:30 – 6:00
Kids Activities
Archaeological Society of Virginia
Eastern Shore Chapter — Native American and Colonial artifacts on display
1:00 – 2:00
Kids Activities
Bracelet Making with The Northampton County YMCA
Create your own nautical bracelet by tying a simple knot—just like sailors have done for generations—using durable rope or cord. A fun, hands-on way to celebrate SailFest and take home a piece of coastal tradition.
1:00 – 3:00
Music
All American Alumni Band
Festival Concert Stage
1:00
History Lecture
Seafaring Heritage and Traditions
Dennis Custis
The Eastern Shore’s original ambassador to the past. A beloved educator and remarkably engaging speaker.Read Bio
1:00 – 3:00
Kids Activities
Knot Tying
1:00 – 3:00
Kids Activities
Burgee Making
2:00 – 4:00
Kids Activities
Salty Critters Petting Zoo
2:00 – 2:30
Music
Williamsburg Field Musick
TBD
2:00
History Lecture
Eastern Shoremen in the American Revolutionary Navy
David Scott, MD
After 30 years practicing medicine on the Shore, David now researches local history in retirement. He brings the Eastern Shore’s role in the Revolutionary War to life.Read Bio
3:00
History Lecture
Patriots of Color and Their Eastern Shore Roots
Tyrone Goodwyn & Luke Alexander
Two historians trace communities of color from Virginia’s Eastern Shore through their pivotal roles in the Revolutionary War.Read Bio
3:30 – 4:00
Music
Williamsburg Field Musick
Festival Concert Stage
4:00
History Lecture
Alexander Hamilton and the Origins of the Coast Guard
Admiral Charles Ray, USCG (Retired)
Retired 31st Vice Commandant of the U.S. Coast Guard. A rare opportunity to hear from a leader who oversaw the most significant Coast Guard buildup since WWII.Read Bio
7:00 – 9:15
Music
Three Sheets to the Wind
Festival Concert Stage
9:15
Kids Activities
Fireworks
Harbor
Sunday, June 21
12:00
Opening Ceremony
Clara Cooper, National Anthem
Top of ramp to docks
12:00 – 6:00
Ship Deck Tours
All Boats Open to Visitors
Docks
12:00 – 6:00
Kids Activities
Virginia Institute of Marine Science Touch Tank
12:00 – 6:00
Kids Activities
Virginia Navy Galley — Norfolk Revenge
Re-enactors Encampment · Harbor
12:00 – 4:00
Kids Activities
Cape Charles Community Sailing Experience
12:30 – 4:30
Kids Activities
Face Painting with Emily’s Fun Faces
12:30 – 6:00
Kids Activities
Archaeological Society of Virginia
Eastern Shore Chapter — Native American and Colonial artifacts on display
12:30 – 2:00
Music
Sonic Ukes
Festival Concert Stage
1:00 – 2:00
Kids Activities
Bracelet Making with The Northampton County YMCA
Create your own nautical bracelet by tying a simple knot—just like sailors have done for generations—using durable rope or cord. A fun, hands-on way to celebrate SailFest and take home a piece of coastal tradition.
1:00
History Lecture
Naval Warfare During the Age of Sail
Captain Craig C. Felker, USN (Retired)
Ph.D. naval historian, retired Navy captain, and Cape Charles resident. His deep expertise makes this account of a pivotal Revolutionary War battle unmissable.Read Bio
1:00 – 3:00
Kids Activities
Knot Tying
1:00 – 3:00
Kids Activities
Burgee Making
2:00 – 4:00
Kids Activities
Salty Critters Petting Zoo
2:00
History Lecture
Rendezvous with Kalmar Nyckel
Jenean Hall
Author of two books on early Eastern Shore history. She will share a story being told publicly for the very first time.Read Bio
2:15 – 2:45
Music
Shore Singers
Festival Concert Stage
3:00
History Lecture
Tides of Time: 250 Years on Virginia’s Eastern Shore
Kentoya Garcia
Kentoya Garcia is a local historian dedicated to preserving and sharing the rich heritage of Virginia’s Eastern Shore. She combines research, storytelling, and public engagement to highlight the people, traditions, and events that have shaped the region across generations.
3:00 – 4:00
Music
The Colonial Singers of Williamsburg
Festival Concert Stage
4:00
History Lecture
Bacon’s Rebellion and Governor Berkeley’s Flight to the Eastern Shore
Andy Dunton
President of the Cape Charles Museum, Marine veteran, and direct descendant of the Shore’s earliest recorded families.Read Bio
4:30 – 6:00
Music
Six String Soldiers
Festival Concert Stage