A yearly tradition at the Colonial Oak: Monroeville is a rock alternative bluegrass band that regularly explores folk and country music genres. Named in honor of legendary bluegrass musician Bill Monroe and fronted by Grammy nominated band leader/owner Matt Munsey, the core band also features versatile vocalists and utility musicians McCoy Borg, Chevy Watson, and Paul Watson.

Davis Loose, an up & coming St. Augustine singer/songwriter,  brings his original and inspired take on Country & Western music to the Oak.

A yearly tradition at the Colonial Oak: Monroeville is a rock alternative bluegrass band that regularly explores folk and country music genres. Named in honor of legendary bluegrass musician Bill Monroe and fronted by Grammy nominated band leader/owner Matt Munsey, the core band also features versatile vocalists and utility musicians McCoy Borg, Chevy Watson, and Paul Watson.

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!

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.

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!