Amy Robbins + MORE! – September 23

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

September brings the Sing Out Loud Showcase to the Oak! Join us for this annual epic celebration of live music in the Nation’s Oldest City! Saturday, September 23 6:00 PM – TBA 7:00 PM – TBA 8:00 PM – Amy Robbins Band 9:00 PM – TBA ***All Sing Out Loud performances at the Oak are free and family friendly***   ...

Free

Charlie Robertson + MORE! – September 24

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

September brings the Sing Out Loud Showcase to the Oak! Join us for this annual epic celebration of live music in the Nation’s Oldest City! Sunday, September 24 3:00 PM – Jim Carrick & Charley Simmons 4:15 PM – Lee Hunter & Joey Kerr 5:30 PM – Marianne Lerbs 6:45 PM – John Winters & Mark Richey 8:00 PM – ...

Free

Improv Comedy Night – September 27

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Your First Coast Comedy veteran professionals have no plan and willingly dive headfirst into almost any challenge the audience will throw at them, resulting in unforgettably hilarious moments. And it gets better! This show is for everyone! You can bring the whole family because these improvisers play smart… to ensure the show is always clean and never mean! Pay-What-You-Will. All ...

pay-what-you-will

Cumberland – September 28

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Country Night at The Colonial Oak Music Park with Cumberland! 7-10 PM Free Admission Family & Pet friendly!

Free

Songwriters Festival – September 29

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Coming all the way from Nashville, Tennessee! Meet the songwriters behind today’s top radio hits. Once a year, The St. Augustine Songwriters Festival brings the artists responsible for top hit country songs to local venues including the Oak! Stop by and enjoy this FREE event with us!   Friday, September 29 2:00 PM – 3:20 PM Aris Smith – Paul ...

Free

Songwriters Festival – September 30

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Coming all the way from Nashville, Tennessee! Meet the songwriters behind today’s top radio hits. Once a year, The St. Augustine Songwriters Festival brings the artists responsible for top hit country songs to local venues including the Oak! Stop by and enjoy this FREE event with us!   Saturday, September 30 2:00 PM – 3:00 PM Jolie – Mick Fury ...

Free

Songwriters Festival – October 1

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Coming all the way from Nashville, Tennessee! Meet the songwriters behind today’s top radio hits. Once a year, The St. Augustine Songwriters Festival brings the artists responsible for top hit country songs to local venues including the Oak! Stop by and enjoy this FREE event with us!   Sunday, October 1 11:10 AM – 11:40 PM Lost Saints   11:40 ...

Free

Improv Comedy Night – October 4

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Your First Coast Comedy veteran professionals have no plan and willingly dive headfirst into almost any challenge the audience will throw at them, resulting in unforgettably hilarious moments. And it gets better! This show is for everyone! You can bring the whole family because these improvisers play smart… to ensure the show is always clean and never mean! Pay-What-You-Will. All ...

pay-what-you-will

Rio Grande Band – October 5

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Head to the Colonial Oak Music Park for Country Night featuring Rio Grande! Enjoy live music, cool drinks from the on-site bars, and even grab dinner from the adjacent St. Augustine Seafood Company! Fun for the whole family. Friendly dogs welcome!

Free

Baba Caiman – October 6

Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

Head to the Colonial Oak Music Park for a latin fusion performance by Baba Caiman! Enjoy live music, cool drinks from the on-site bars, and even grab dinner from the adjacent St. Augustine Seafood Company! Fun for the whole family. Friendly dogs welcome!

Free