October 16 Let ’ s Ride Brass Band at the Colonial Oak Music Park This free family and pet friendly performance takes place from 6-9 p . m . Colonial Oak Music Park , 21 St . George St ., St . Augustine . www . thecolonialoakmusicpark . com
October 21 Steve Vai at Ponte Vedra Concert Hall Doors open at 7 p . m ., show starts at 8 p . m . Tickets are $ 49.50- $ 89.50 . Ponte Vedra Concert Hall , 1050 A1A N ., Ponte Vedra Beach . 904-209-0367 www . pvconcerthall . com
October 22 Jail Break 5K Make a break from St . Augustine at the Jail Break 5K race that takes participants from the authentic Old Jail across the Vilano Bridge , through Porpoise Point , ending at the Vilano Beach access . The race starts at 8 a . m . Registration is $ 25- $ 40 . 167 San Marco Ave ., St . Augustine . 904-547-7120 www . runsignup . com / Race / FL / SaintAugustine / EscapeFromStAugustine
October 22 Vilano Beach Music Fest Plan an entertaining Saturday at Vilano Beach with the sounds of the all-female “ sirens ” of the area . Performers in the lineup include Mallory Jen , Amy Hendrickson , Chelsea Saddler ’ s Bad Dog Mama , and the Duffy Bishop Band . In addition to great music , enjoy food trucks , raffles , arts and craft vendors and more . Vilano Beach ’ s North Shores Community Park , 120 Meadow Ave . St . Augustine . 904-540-0402 www . vilanobeachfl . com
October 22 Live from The Waterworks : A Gamble Rogers Concert Series – Doyle Dykes with Ruth Wyand The St . Johns Cultural Council and Gamble Rogers Music Festival present a new concert series honoring the legacy of legendary St . Augustine performer Gamble Rogers . Concerts take place on the Saturday of the third full weekend of each month at The Waterworks , a venue constructed in 1898 and listed on the National Register of Historic Places . October ’ s event features world-renowned fingerstyle guitarist Doyle Dykes with an opening performance by Ruth Wyand . Doors open at 7 p . m . and the show starts at 7:30 p . m . Ticket prices begin at $ 20 . The Waterworks , 184 San Marco Ave ., St . Augustine . 904-808-7330 www . historiccoastculture . com
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