Hip Happenings This Weekend In Jacksonville & St. Augustine!

Barbie Brooksher
Barbie Brooksher
Published on May 5, 2022

Happy first weekend of May! We are pleased to wish all a Happy Mother’s Day as well and have come up with our hip happenings this weekend in Jacksonville and St. Augustine. Here’s a great variety of events this weekend for you.

Please send us pictures at [email protected] so we can post the fun you’re having! Also, if you read about it here be sure to mention it at the vendor location! Tell them you found out about the event from Beach Life With Barbie!


Friday, May 6 – Sunday, May 8

Gamble Rogers Music Festival

Colonial Oak Music Park, 21 St George St, St. Augustine, FL

Join us for the Gamble Rogers Music Festival on May 6-8, 2022. This annual event honors “modern troubadour” James Gamble Rogers.  The music festival includes more than 30 musical acts, with headliners The Steel Wheels, an Americana band from the Virginia mountains.

Stages will be set up throughout the Colonial Quarter for your listening pleasure: Main Stage, Mulberry Stage, and Pickers’ Stage.  The Riberia Gardens stage (new this year) will feature youth-friendly performances and activities including a ukulele workshop, storytelling, hands-on music-making, and family-friendly music. It is located across the street from Colonial Oak Music Park.

Food and drinks are available at the Colonial Quarter’s restaurants and beverage sales areas.  There is also a jam area, merchandise, and more.

Performance Dates/Times:
Friday, May 6, 2022      —  5:00pm-10:30pm
Saturday, May 7, 2022 — 10:00am-10:30pm
Sunday, May 8, 2022    — 10:00am- 6:00pm

Ticket Prices:
$60.00 — all 3-days
$20.00 — Friday, May 6
$30.00 — Saturday, May 7
$20.00 — Sunday, May 8


Saturday, May 7 • 2 PM – 7 PM

Jumping for Drew & You Foundation

Latham Plaza & Seawalk Pavilion, 11 1st Street N, Jacksonville Beach, FL

Jumping for Drew & You Foundation Details: 

“I’m Daryl Rosenberger, a native of Jacksonville, Florida. My youngest son, Andrew (Drew) Rosenberger, took his life at the age of 30 in October of 2020. 

Drew struggled for many years and was diagnosed with Bipolar Disorder two years before his passing.

When this happens to a person, a parent especially, you feel like you need to do something to give back. I’ve given a great deal of thought to what I can do to ease the pain and assist others, all in an effort to potentially help a young man or woman who may not be in a financial position to get the counseling and/or medication he/she may need.

I’m an ordinary man who is seeking sponsorships and donations to give back to those in need.”

Come walk the last mile with Daryl, Diane, Family, and Friends as Daryl completes his journey for suicide and bipolar prevention and honors his Son, Drew! There will be a BIG Celebration of LIFE with live music, food, fun, libations, and lots of hugs!

All tickets are DONATION based and your donation is the entry to the event. No minimum!

Please bring your own chairs to camp out and listen to the great music! Limited seating will be available.


Saturday, May 7 • 11 AM – 4 PM

Seaside’s May Festival

Seaside School Consortium, Inc., 2865 Mayport Road, Jacksonville, FL

Join us for a day of family fun! 2865 Mayport Rd. 11 am-4 pm. We will have crafts for kids, attractions, vendors, food trucks, and more! Free entry, everyone is welcome!

In May, we celebrate May Faire, an ancient festival to welcome spring. As the days get longer, the sun brightens not only the outer world but our inner selves too. The celebration is abundant with fresh flowers, a Maypole, music, food, and dancing. We are offering this lovely celebration to the greater community in the form of a lively public festival. Come out and celebrate with Seaside Charter Schools. All proceeds support Seaside Charter Schools and our mission. Much of this event is free, some craft tables have a small fee varying between $1-$5.


Saturday, May 7 • 8 AM – 5 PM

22nd Annual Wildwood Fishing Tournament

St. Augustine Boating Club, 611 Boating Club Road, St. Augustine, FL

At the St. Augustine Youth Services event, Fishing begins at Safe Light, with a weigh-in from 11 am to 5 pm. Cost is $30 per angler, with Cash Prizes and Calcutta. On Friday, May 6th from 5 to 8 pm is the Mandatory Captain’s Meeting.

On Saturday, bring your family and friends from 3-6 pm for food trucks, raffles, and fun!

Pre-Register Here!


Sunday, May 8 • 9 AM – 4 PM

Mother’s Day Brunch & Spring Market

Wicked Barley Brewing Company, 4100 Baymeadows Rd Jacksonville, FL 32217

Join us for Wicked Barley’s annual Mother’s Day Brunch & Spring Market on Sunday, May 8th from 9 am ’til 4 pm. Treat MOM to a delicious, from-scratch Sunday Brunch, Live Music, and a variety of Local Vendors! Sip and Shop with local vendors from 11 am ’til 4 pm. Live music with Tad Jennings from 11 AM – 3 PM.


Sunday, May 8 • 7 PM – 11 PM

John Fogerty at the St. Augustine Amphitheater

St Augustine Amphitheater, 1340C A1A South, St. Augustine, Florida 

John Fogerty is a true American treasure.  As the leader of Creedence Clearwater Revival, Fogerty forged a distinctive, groundbreaking sound all his own, equal parts blues, country, pop, rockabilly, R&B, swamp boogie, and Southern-fried rock ‘n’ roll, all united by his uniquely evocative lyrical perspective.  Fogerty is a Grammy winner and has been inducted into the Rock & Roll Hall of Fame as well as the Songwriters Hall of Fame.  He is the only musician to be inducted into the Baseball Hall of Fame for his song, “Centerfield,” a staple at baseball stadiums across the country.

Among Fogerty’s many hit songs, both as a solo artist and as leader of CCR, highlights include “Centerfield,” “Proud Mary,” “Susie Q,” “Fortunate Son,” “Born on the Bayou,” “Bad Moon Rising,” and “Have You Ever Seen the Rain,” among many others.  Tickets are still available.


Let us know what you’re up to this weekend, we’d love to hear from you! What do you like to do over the weekend? Do you have any hip happenings to share with us? We would love to hear … email me at [email protected].

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