Colonial Quarter

The Pauses + MORE! – September 16
2023-09-16 19:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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 16
7:00 PM – Ghost Tropic
8:00 PM – Evening Standards
9:00 PM – The Pauses
***All Sing Out Loud performances at the Oak are free and family friendly***

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Ghost Tropic

The Pauses

Grant Peeples + MORE! – September 17
2023-09-17 15:00 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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 17
3:00 PM – Skin & Bonz
4:15 PM – The Taildraggers
5:30 PM – The Thick & Thin String Band
6:45 PM – Wild Shiners
8:00 PM – Grant Peeples
***All Sing Out Loud performances at the Oak are free and family friendly***
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Grant Peeples

Skin & Bonz

Thick & Thin String Band

Wild Shiners

Improv Comedy Night – September 20
2023-09-20 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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 seating is General Admission.

No ticket is better than any other. Just pay what you think the experience is worth

The Chris McNeil Band – September 21
2023-09-21 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Country Night with The Chris McNeil Band at the Oak!
7-10 PM
Free Admission
Family & Pet friendly!

Ramona & The Riot + MORE! – September 22
2023-09-22 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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!
Friday, September 22
6:00 PM – Billy Buchanan & His Rock ‘N Soul Revue
7:30 PM – TBA
9:00 PM – Ramona & The Riot
***All Sing Out Loud performances at the Oak are free and family friendly***

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Billy Buchanan

Ramona & the Riot

Amy Robbins + MORE! – September 23
2023-09-23 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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***

Amy Robbins

Charlie Robertson + MORE! – September 24
2023-09-24 15:00 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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 – Charlie Robertson
***All Sing Out Loud performances at the Oak are free and family friendly***

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Mark Richey

Marianne Lerbs

Improv Comedy Night – September 27
2023-09-27 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Cumberland – September 28
2023-09-28 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Country Night at The Colonial Oak Music Park with Cumberland!
7-10 PM
Free Admission
Family & Pet friendly!

Songwriters Festival – September 29
2023-09-29 14:00 - 21:30 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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 Orehovec – Emmet Stevens Jr
3:30 PM – 5:00 PM
Lauren Hungate – Davis Loose – Mel Washington
5:10 PM – 6:40 PM
Russell Sutton – Tofur Brown – David Tolliver
6:50 PM – 7-20 PM
War Hippies
7:30 PM – 9:30 PM
Dave Berg – Brady Seals – Danny Myric

Songwriters Festival – September 30
2023-09-30 14:00 - 23:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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
3:10 PM – 4:40 PM
Jamie Floyd – Jaida Dreyer – Chad Warrix
4:50 PM – 6:20 PM
Jesse Rice – Taylor Austin Dye – Cliff Cody
6:40 PM – 7:40 PM
Rob Williford – McCoy Moore

7:50 PM – 9:10 PM
Ronnie Bowman – Andy Albert – Adam Hood
9:20 PM – 10:50 PM
Bobby Pinson – Matt Dragstrem – Justin Wilson

Songwriters Festival – October 1
2023-10-01 11:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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 AM – 1:20 PM
Brian Davis – Murphy Elmore – McCoy Moore – Dave Brainard
1:30 PM – 2:50 PM
Lauren Hungate – Jenny Tolman – Jaida Dreyer
6:50 PM – 7-20 PM
War Hippies
3:00 PM – 4:50 PM
AJ Cross – Chris Blair – Preston James – Mick Fury

Improv Comedy Night – October 4
2023-10-04 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Rio Grande Band – October 5
2023-10-05 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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!

Baba Caiman – October 6
2023-10-06 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, 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!

Dewey Via Band – October 7
2023-10-07 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Head to the Colonial Oak Music Park for local favorite, The Dewey Via Band!
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!

Sports Sunday – October 8
2023-10-08 12:00 - 19:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us for sports all Sunday long on our 128″ video wall at the Oak! Football season, it’s NFL football. Baseball Season, it’s MLB. Premier League Soccer matches, Basketball too. We have food and drinks for sale, so all you need is your team spirit!

Improv Comedy Night – October 11
2023-10-11 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Closed for Private Event – October 12
2023-10-12 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Closed for Private Event

Dogtoberfest feat. Dyer Davis Band – October 13
2023-10-13 19:00 - 22:00
Sierra Nevada Brewing Co. is bringing Dogtoberfest to the Oak!
On this special evening, all profits from Oak bars will go towards supporting Ayla’s Acres No-Kill Animal Rescue.

– Friday, October 13 from 7-10 PM
– Free show by Dyer Davis Group
– Dress your pups up for the the chance to win best dog costume!
– 50/50 raffles
– Silent auction items
– Fun to be had for all ages!

Be sure to stop by, grab a drink, all in support of Ayla’s Acres No-kill Animal Shelter!
See you at the Oak!

Caravel Concert Series feat. Whalin – October 14
2023-10-14 19:00 - 22:00 | Colonial Quarter
Whalin is ready to rock the Colonial Quarter’s new stage on Saturday, October 14! 7-10 PM
Don’t miss this epic show brought to you in partnership with the St. Augustine Distillery.
Free Admission
Family Friendly
Multiple bars on site featuring St. Augustine Distillery spirits.
See you there!

Sports Sunday! – October 15
2023-10-15 12:00 - 19:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Improv Comedy Night – October 18
2023-10-18 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Whalin – October 19
2023-10-19 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Country Night at the Oak featuring Whalin!
7-10 PM
FREE Admission
Family friendly!

Earth Tonez – October 20
2023-10-20 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Head to the Colonial Oak Music Park for a show by Earth Tonez! 7-10 PM
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!

Ramona & The Riot! – October 21
2023-10-21 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Head to the Colonial Oak Music Park for Ramona & The Riot! 7-10 PM
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!

Sports Sunday – October 22
2023-10-22 12:00 - 19:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us for sports all Sunday long on our 128″ video wall at the Oak! Football season, it’s NFL football. Baseball Season, it’s MLB. Premier League Soccer matches, Basketball too. We have food and drinks for sale, so all you need is your team spirit!
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Improv Comedy Night – October 25
2023-10-25 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Playin’ Possum – October 26
2023-10-26 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Head to the Colonial Oak Music Park for Country Night featuring Playin’ Possum!
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!

Spooktacular at The Colonial Quarter
2023-10-27 18:30 - 2023-10-29 21:30 | Colonial Quarter
For 3 nights the Grounds of the Colonial Quarter will transform into a Family-Friendly Halloween experience. Come see a Pirate ship complete with a full crew of skeleton pirates, a mermaid grotto w/live mermaids, the Rustier Cutlass Pirate Band, and a creepy cemetery with some historic St Augustine stories.

October 27, 28, & 29
Open each night from 6:30 – 9:30 PM
$12 Adults
$7 Children
