Four days of tall ships, live music, history, and celebration along Portsmouth’s historic waterfront. June 19–22, 2026.
Free & open to the public
Friday
June 19
Juneteenth
7am – 12pm
Parade of Sails
Hampton Roads Harbor - Portsmouth Waterfront
Portsmouth’s waterfront provides the perfect vantage point to enjoy the dozens of tall ships arriving from Lynnhaven Anchorage to dock on both sides of the Elizabeth River. An added treat this year is…
FREESIGNATURE EVENT
Time TBC
Blue Angels Flyover
Portsmouth & Norfolk Waterfront
The U.S. Navy Blue Angels perform a flyover of Hampton Roads in conjunction with the Parade of Sails.
FREE
1pm – 6pm
Public Tall Ship Deck Tours
Ship locations TBC
Board the visiting tall ships and meet their crews. Explore the decks, rigging, and history up close.
FREE
Saturday
June 20
11am – 6pm
Public Tall Ship Deck Tours
Ship locations TBC
Board the visiting tall ships and explore their decks, rigging, and history up close.
FREE
Sunday
June 21
11am – 6pm
Public Tall Ship Deck Tours
Ship locations TBC
Board the visiting tall ships and explore their decks, rigging, and history up close.
FREE
Monday
June 22
11am – 6pm
Public Tall Ship Deck Tours
Ship locations TBC
Board the visiting tall ships and explore their decks, rigging, and history up close.
FREE
Friday
June 19
Juneteenth
9am – 10:30am
Underground Railroad Walking Tour
637 North St, Portsmouth
This lively excursion begins with an interior tour of the perfect stop on the UGRR: Emanuel AME. Guided through the street of Historic Olde Towne by historic figures from Portsmouth's past, guests mee…
FREE
11am – 12pm
St. John's Episcopal Church
424 Washington Street, Portsmouth
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
Henry Lewis & Clarissa Davis hold a captivating afternoon performance along the High Street East corridor and Landing.
FREE
11am – 5pm
History Alive: Strolling Interpreters
North Street Landing & Hotel
Two Union Soldiers hold a captivating live performance at the North Street Landing.
FREE
11am – 8pm
MEET PORTSMOUTH’S HISTORIC CHARACTERS FROM THE AGE OF SAIL
High Street West
Clarissa Davis – freedom seeker who hid under a Portsmouth porch for 75 days after missing her rendezvous with the ship that eventually carried her North to freedom.
Major F.W. Emery – Assistant Adju…
FREE
12pm – 3pm
Monumental United Methodist Church
450 Dinwiddie Street, Portsmouth
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
FREE
12:45pm – 4pm
EMANCIPATION – FOUR DRAMATIC PRESENTATIONS
Green Street Stage, Olde Towne
12:45 p.m. – Lift Every Voice and Sing followed by Welcome by Mayor Shannon E. Glover.
1 p.m. – Crossed Sword/Crossed Hope presented by The Not Just For February Players.
1:30 p.m. – Sounds Like Fre…
FREE
2pm – 8pm
History Alive: Strolling Interpreters
High Street West
Josephine Norcom and Pauline Adams hold a live performance along High Street West.
FREE
4pm
JUNETEENTH the song NATIONAL DEBUT
Green Street Stage, Olde Towne
Grammy-nominated music producer Mark L. Carman’s powerful anthem to Freedom Day makes its national debut immediately following “Juneteenth: The Bittersweet Challenge” as the finale to a collection of…
FREE
7pm – 9:30pm
Underground Railroad Walking Tour
637 North St, Portsmouth
This lively excursion begins with an interior tour of the perfect stop on the UGRR: Emanuel AME. Guided through the street of Historic Olde Towne by historic figures from Portsmouth's past, guests mee…
FREE
All Day
Road to Revolution Signage
Various Portsmouth Locations
Explore Road to Revolution, a series of outdoor historical markers highlighting significant locations, events, and individuals that shaped the American Revolution, the Revolutionary War, and the natio…
FREE
All Day
Path of History Self-Guided Tour
Various Historic Portsmouth Locations
Many influential leaders have shaped the course of human events from our city. You will unveil more than 250 years of American history during this Walking Tour – from the home that the Union Army’s Pr…
A new mural of American naval officer, Richard Dale, will be available for viewing during the entire weekend.
FREE
Saturday
June 20
9am – 10:30am
Home & History Tour
Olde Towne Portsmouth
A guided morning walking tour through Olde Towne's historic homes and architecture. See places occupied or visited by William Flora, General Lafayette, General Cornwallis, Benedict Arnold, James Fayet…
FREE
11am – 2pm
St. John’s Episcopal Church
424 Washington Street, Portsmouth
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
High Street East, High Street Landing & North Landing
William Flora, Colonel Titus, Sailor (M & F), and Dr. Collins bring the revolutionary era to life across the waterfront district.
FREE
12pm – 3pm
Hill House Museum
221 North St, Portsmouth
As we celebrate the 250th anniversary of our nation's founding, the Hill House Museum reflects on members of the Hill ancestral line who lived and breathed the tumult of the Revolutionary War. An inte…
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
FREE
1pm
Richard Dale Mural Dedication
720 County Street, Corner of Effingham Street
There will be a dedication ceremony for the new mural of American naval officer, Richard Dale, on County Street near the Corner of Effingham Street. All are welcome to attend. For more information, pl…
FREE
2pm – 8pm
History Alive: Strolling Interpreters
High Street West
Capt. Crawford & Mrs. Crawford hold afternoon and evening performances in the western corridor.
FREE
7pm – 8:30am
Home & History Tour
Olde Towne Portsmouth
A guided evening walking tour through Olde Towne's historic homes and architecture. See places occupied or visited by William Flora, General Lafayette, General Cornwallis, Benedict Arnold, James Fayet…
FREE
All Day
Road to Revolution Signage
Various Portsmouth Locations
Explore Road to Revolution, a series of outdoor historical markers highlighting significant locations, events, and individuals that shaped the American Revolution, the Revolutionary War, and the natio…
FREE
All Day
Path of History Self-Guided Tour
Various Historic Portsmouth Locations
Many influential leaders have shaped the course of human events from our city. You will unveil more than 250 years of American history during this Walking Tour – from the home that the Union Army’s Pr…
A new mural of American naval officer, Richard Dale, will be available for viewing during the entire weekend.
FREE
Sunday
June 21
8am – 12pm
Trinity Episcopal Church
500 Court Street, Portsmouth
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
FREE
8am – 2pm
St. John’s Episcopal Church
424 Washington Street, Portsmouth
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
FREE
11am – 3pm
Monumental United Methodist Church
450 Dinwiddie Street Portsmouth, VA 23704
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
FREE
12pm – 6pm
History Alive: Strolling Interpreters
High Street East & Landing
Two women, both named Eliza Bains, bring a captivating afternoon performance along the High Street East corridor and Landing.
FREE
2pm – 8pm
History Alive: Strolling Interpreters
North Street Landing
John Thompson Hill & Eliza Hill hold afternoon and evening performances at the North Street Landing.
FREE
All Day
Road to Revolution Signage
Various Portsmouth Locations
Explore Road to Revolution, a series of outdoor historical markers highlighting significant locations, events, and individuals that shaped the American Revolution, the Revolutionary War, and the natio…
FREE
All Day
Path of History Self-Guided Tour
Various Historic Portsmouth Locations
Many influential leaders have shaped the course of human events from our city. You will unveil more than 250 years of American history during this Walking Tour – from the home that the Union Army’s Pr…
A new mural of American naval officer, Richard Dale, will be available for viewing during the entire weekend.
FREE
Monday
June 22
11am – 2pm
St. John's Episcopal Church
424 Washington Street, Portsmouth
Visitors are invited to explore Olde Towne, Portsmouth’s historic churches during designated open viewing hours. This self-guided experience provides an opportunity to appreciate the city's rich archi…
Capt. Fountain, George Teamoh, Ebenezer Thompson, and Jack Sparrow perform along the waterfront on the festival's final day.
FREE
All Day
Road to Revolution Signage
Various Portsmouth Locations
Explore Road to Revolution, a series of outdoor historical markers highlighting significant locations, events, and individuals that shaped the American Revolution, the Revolutionary War, and the natio…
FREE
All Day
Path of History Self-Guided Tour
Various Historic Portsmouth Locations
Many influential leaders have shaped the course of human events from our city. You will unveil more than 250 years of American history during this Walking Tour – from the home that the Union Army’s Pr…
Build it. Float it. Move it. Stop by our mobile classroom to design and build your own miniature cargo barges using engineering and creativity to tackle a real-world maritime challenge: Can your barge…
FREE
11am – 4pm
Sensory Room for Kids
Children's Museum of Virginia
The Children's Museum will have its Sensory Room open throughout the weekend, located in the side room next to the birthday party room.
11am – 8pm
Aerial Performance and Play with Visual Artistry Entertainment
Museum Mall
Experience the beauty and athleticism of aerial arts as a professional performer from Visual Artistry Entertainment takes to the air on an aerial hoop. Combining strength, grace, and acrobatic skill,…
11am – 11pm
Carnival
High Street - Blocks 100, 200 & 300
Three blocks of family fun - face painters, caricature artists, balloon art, mini zoo, and mascots. Featuring a Double Ferris Wheel on Water Street, Carousel, Wave Thunder, and Willy the Whale!
FREE TO ATTEND
2pm – 8pm
Jack's Jungle Ultimate Petting Zoo
Middle Street
Get up close with fascinating animals at Jack’s Jungle Ultimate Petting Zoo, an interactive educational experience featuring mammals and reptiles from around the world. Designed to inspire curiosity,…
FREE
7:30pm
Friday Night Flix: Zootopia 2
Portsmouth Pavilion
Bring the whole family for Zootopia 2! Event is FREE and OPEN TO THE PUBLIC. Doors open at 7:30PM and the movie starts at sundown. Outside food is welcome. No outside alcohol will be permitted.
Build it. Float it. Move it. Stop by our mobile classroom to design and build your own miniature cargo barges using engineering and creativity to tackle a real-world maritime challenge: Can your barge…
FREE
10am – 4pm
ASNE-Sika Ultimate Build-A-Boat Challenge
North Landing, Olde Towne Portsmouth
Watch 20 two-person teams construct and design boats from scratch in preparation for race day.
The Children's Museum will have its Sensory Room open throughout the weekend, located in the side room next to the birthday party room.
11am – 8pm
Aerial Performance and Play with Visual Artistry Entertainment
Museum Mall
Experience the beauty and athleticism of aerial arts as a professional performer from Visual Artistry Entertainment takes to the air on an aerial hoop. Combining strength, grace, and acrobatic skill,…
11am – 11pm
Carnival
High Street - Blocks 100, 200 & 300
Three blocks of family fun - face painters, caricature artists, balloon art, mini zoo, and mascots. Featuring a Double Ferris Wheel on Water Street, Carousel, Wave Thunder, and Willy the Whale!
FREE TO ATTEND
12pm – 4pm
Magic Circus Shows by MerMan
Museum Mall
Experience an unforgettable blend of comedy, magic, and audience participation with MerMan, a nationally touring entertainer with more than 30 years of experience. Featuring mind-bending illusions, fa…
FREE
2pm – 8pm
Jack's Jungle Ultimate Petting Zoo
Middle Street
Get up close with fascinating animals at Jack’s Jungle Ultimate Petting Zoo, an interactive educational experience featuring mammals and reptiles from around the world. Designed to inspire curiosity,…
The Children's Museum will have its Sensory Room open throughout the weekend, located in the side room next to the birthday party room.
11am – 11pm
Carnival
High Street - Blocks 100, 200 & 300
Three blocks of family fun - face painters, caricature artists, balloon art, mini zoo, and mascots. Featuring a Double Ferris Wheel on Water Street, Carousel, Wave Thunder, and Willy the Whale!
FREE TO ATTEND
12pm – 4pm
Magic Circus Shows by MerMan
Museum Mall
Experience an unforgettable blend of comedy, magic, and audience participation with MerMan, a nationally touring entertainer with more than 30 years of experience. Featuring mind-bending illusions, fa…
FREE
12pm – 4pm
Bubble Art and Sidewalk Chalk
Museum Mall
There will be bubble art and chalk for kids to play with outside of the Museum Mall.
FREE
2pm – 8pm
Jack's Jungle Ultimate Petting Zoo
Middle Street
Get up close with fascinating animals at Jack’s Jungle Ultimate Petting Zoo, an interactive educational experience featuring mammals and reptiles from around the world. Designed to inspire curiosity,…
FREE
2:30pm – 4:30pm
ASNE-Sika Ultimate Build-A-Boat Challenge
North Landing, Olde Towne Portsmouth
It's race day! Watch 20 two-person teams put their newly constructed boats to the test on the water.
Build it. Float it. Move it. Stop by our mobile classroom to design and build your own miniature cargo barges using engineering and creativity to tackle a real-world maritime challenge: Can your barge…
FREE
11am – 4pm
Sensory Room for Kids
Children's Museum of Virginia
The Children's Museum will have its Sensory Room open throughout the weekend, located in the side room next to the birthday party room.
11am – 11pm
Carnival
High Street - Blocks 100, 200 & 300
Three blocks of family fun - face painters, caricature artists, balloon art, mini zoo, and mascots. Featuring a Double Ferris Wheel on Water Street, Carousel, Wave Thunder, and Willy the Whale!
As we celebrate the 250th anniversary of our nation's founding, the Hill House Museum reflects on members of the Hill ancestral line who lived and breathed the tumult of the Revolutionary War. An inte…