Here are some shows, taking place in Jacksonville and nearby cities, from May 17 to May 21, 2026: • Chicago at Florida Theatre (May 19, 2026) • Protoje at Colonial Oak Music Park (May 20, 2026) • Willie Nelson at The St. Augustine Amphitheatre (May 21, 2026)

Chicago at Florida Theatre (May 19, 2026)

May 19, 2026 Tuesday
Chicago
at Florida Theatre
floridatheatre.com

The Chicago band is actually from Chicago, Illinois. The rock/jazz/pop group will be headlining the Florida Theatre, in Jacksonville, on May 19, 2026.

Tour Dates

MAY 01 Brandon Amphitheater Brandon, MS
MAY 02 Grand Event Center at Golden Nugget Lake Charles, LA
MAY 05 Shreveport Municipal Auditorium Shreveport, LA
MAY 06 Cadence Bank Arena Tupelo, MS
MAY 08 Beau Rivage Theatre Biloxi, MS
MAY 09 Beau Rivage Theatre Biloxi, MS
MAY 10 Beau Rivage Theatre Biloxi, MS
MAY 13 Montgomery Performing Arts Centre Montgomery, AL
MAY 14 Donald L. Tucker Civic Center Tallahassee, FL
MAY 16 Johnny Mercer Theatre Savannah, GA
MAY 17 The Bell Auditorium Augusta, GA
MAY 19 Florida Theatre Jacksonville, FL
MAY 21 Crown Theatre Fayetteville, NC
MAY 22 The Pantheon at Caesers Virginia Danville, VA
MAY 23 Peace Center Greenville, SC
MAY 26 Tennessee Theatre Knoxville, TN
MAY 27 Opry House Nashville, TN
MAY 29 Chicago Soldiers and Sailors Memorial Auditorium Chattanooga, TN
JUN 14 Mayo Performing Arts Center Morristown, NJ
JUN 17 Allianz Amphitheater at Riverfront Richmond, VA
JUN 18 The Dome by Rutter Mills Virginia Beach, VA
JUN 20 the Clay Center Charleston, WV
JUN 21 Steven Tanger Center for the Performing Arts Greensboro, NC
JUN 23 Hershey Theater Hershey, PA
JUN 24 Proctors Theatre Schenectady, NY
JUN 26 CMAC Canandaigua, NY
JUN 27 Hard Rock Hotel and Casino Ottawa Ottawa, ON
JUN 29 Fox Theatre Detroit Detroit, MI
JUN 30 the Toledo Zoo Amphitheatre Toledo, OH
JUL 01 The Louisville Palace Louisville, KY

Protoje at Colonial Oak Music Park (May 20, 2026)

May 20, 2026 Wednesday
Protoje
with Jesse Royal
at Colonial Oak Music Park
thecolonialoakmusicpark.com

Two-time Grammy-nominated reggae visionary Protoje (Oje Ollivierre) will be headlining the Colonial Oak Music in St Augustine, Florida, on May 20, 2026.

Jesse Royal to open.

Tour Dates

APR 15 – Santa Ana, CA – Observatory
APR 16 – San Diego, CA – Music Box
APR 17 – Phoenix, AZ – Reggae Rise Up AZ
APR 18 – Las Vegas, NV – Reggae in the Desert
APR 19 – Austin, TX – Austin Reggae Festival
APR 21 – Dallas, TX – Ferris Wheelers
APR 22 – Houston, TX – House of Blues
APR 24 – New Orleans, LA – New Orleans Jazz & Heritage Festival
APR 26 – Atlanta, GA – Variety Playhouse
APR 28 – Charlotte, NC – Neighborhood Theatre
APR 30 – New York, NY – Racket
MAY 1 – Boston, MA – Brighton Music Hall
MAY 2 – Hartford, CT – Webster Theatre
MAY 3 – Silver Spring, MD – Fillmore
MAY 8 – Los Angeles, CA – El Rey Theatre
MAY 9 – Santa Cruz, CA – The Catalyst
MAY 10 – Berkeley, CA – UC Theatre
MAY 12 – Portland, OR – Aladdin Theater
MAY 13 – Seattle, WA – Showbox
MAY 16 – Salt Lake City, UT – Soundwell
MAY 17 – Morrison, CO – Red Rocks Amphitheatre
MAY 20 – St. Augustine, FL – Colonial Music Park
MAY 21 – Stuart, FL – Terra Fermata
MAY 22 – Miami, FL – Miami Beach Bandshell
MAY 23 – St. Petersburg, FL – Jannus Live
MAY 24 – Fort Myers, FL – The Ranch

Willie Nelson at The St. Augustine Amphitheatre (May 21, 2026)

May 21, 2026 Thursday
Willie Nelson
at St. Augustine Amphitheatre
theamp.com

The great Willie Nelson will be bringing his seven-decade of Willie Nelson to the St. Augustine Amphitheatre to St Augustine, Florida.

If you like Outlaw music, there’s an upcoming return of the 2026 Outlaw Music Festival Tour that is coming to a city near you. The headliner for the traveling music festival will be Willie Nelson.

Details with scheduled performers listed below:

Friday, July 3, 2026 – The Pavilion at Toyota Music Factory, Irving, TX
Willie Nelson & Family
Wilco
Sheryl Crow
Lukas Nelson
Stephen Wilson Jr.
Margo Price
Lily Meola

Saturday, July 4, 2026 – Germania Insurance Amphitheater, Austin, TX
Willie Nelson & Family
Billy Strings
Wilco
Sheryl Crow
Lukas Nelson
Stephen Wilson Jr.
Margo Price
Rodney Crowell
Lily Meola

Sunday, July 5, 2026 – The Cynthia Woods Mitchell Pavilion
sponsored by Huntsman, The Woodlands, TX
Willie Nelson & Family
Wilco
Sheryl Crow
Stephen Wilson Jr.
Margo Price
Lily Meola

Tuesday, August 18, 2026 – Hollywood Casino Amphitheater, Maryland Heights, MO
Willie Nelson & Family
The Avett Brothers
Lukas Nelson
Stephen Wilson Jr.
Sierra Hull
Don Was and the Pan-Detroit Ensemble

Wednesday, August 19, 2026 – Mystic Lake Amphitheater, Shakopee, MN
Willie Nelson & Family
The Avett Brothers
Lukas Nelson
Sierra Hull
Don Was and the Pan-Detroit Ensemble

Friday, August 21, 2026 – Alpine Valley Music Theatre, East Troy, WI
Willie Nelson & Family
The Avett Brothers
Lukas Nelson
Stephen Wilson Jr.
Sierra Hull
Don Was and the Pan-Detroit Ensemble

Saturday, August 22, 2026 – Pine Knob Music Theatre, Clarkston, MI
Willie Nelson & Family
The Avett Brothers
Lukas Nelson
Stephen Wilson Jr.
Sierra Hull
Don Was and the Pan-Detroit Ensemble

Sunday, August 23, 2026 – Ruoff Music Center, Noblesville, IN
Willie Nelson & Family
The Avett Brothers
Lukas Nelson
Stephen Wilson Jr.
Sierra Hull
Don Was and the Pan-Detroit Ensemble

Tuesday, August 25, 2026 – Credit Union 1 Amphitheatre, Tinley Park, IL
Willie Nelson & Family
The Avett Brothers
Lukas Nelson
Stephen Wilson Jr.
Sierra Hull
Don Was and the Pan-Detroit Ensemble

Friday, August 28 2026 – Northwell at Jones Beach Theater, Wantagh, NY
Willie Nelson & Family
The Avett Brothers
Sheryl Crow
Stephen Wilson Jr.
Robert Randolph
Don Was and the Pan-Detroit Ensemble

Saturday, August 29, 2026 – Bethel Woods Center for the Arts, Bethel, NY
Willie Nelson & Family
The Avett Brothers
Sheryl Crow
Stephen Wilson Jr.
Robert Randolph
Don Was and the Pan-Detroit Ensemble

Sunday, August 30, 2026 – Albany Med Health System at SPAC, Saratoga Springs, NY
Willie Nelson & Family
The Avett Brothers
Sheryl Crow
Stephen Wilson Jr.
Robert Randolph
Don Was and the Pan-Detroit Ensemble