The founder and flat picking front man of Grandpa’s Cough Medicine has moved back to Florida. Brett Bass is shedding his outlaw skin to bring the family friendly, hard driving, high energy bluegrass sound of his powerful guitar and songwriting to  The Colonial Oak Music Park!

Come spend a magical Christmas Eve with Jolie at The Colonial Oak Music Park in downtown St. Augustine! Join Jolie at the Oak this Christmas Eve from 5-8 pm for a holiday show featuring your Christmas favorites and special performances with her family throughout the night. Bring your family, friends, and your ugly Christmas sweaters and ring in the holiday ...

St. Augustine, Florida native, Christian Powers is a singer/songwriter with a musical style steeped in americana folk pop that reflects his passion for the ocean and wholesome living.

One of St. Augustine’s busiest and most in demand bands. RAMONA is sure to bring their own brand of enjoyable and fun music to the Colonial Oak!

An exceptional and vocally driven performer, St. Augustine’s Kyra Livingston blends pop, rock, jazz, soul, blues, and funk into a delectable cascade of musical glory.

An original band grounded in a reggae influence, I-Vibes was founded in 2010. They continue to cover new ground, merging and fusing many elements of musical expression. A great band for a night at the Oak!

JIVEWIRE is a four piece out of St. Augustine, FL that always brings a wide-range of musical options. They play familiar tunes that you can dance to; from Hall & Oates to Maroon 5, Sublime to Bill Withers, they have it covered.

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!

Get yourself ready to dance as Northeast Florida’s favorite blend of R&B, Soul, Funk, and Neo-Soul comes back to the Colonial Oak Music Park!

Ring in 2020 with Florida’s premier Latin Fusion band! Always a fun show, especially as we count down the end of the year.