This Weekend in St. Augustine: Events & Things to Do

Looking for something to do this weekend in St. Augustine & Ponte Vedra?

COVID-19 Update: Out of an abundance of caution due to the COVID-19 Coronavirus, many community events have been postponed or canceled. Please check with individual event organizers for more details.

Check out the top weekend events this May:

The Liqui Moly Pro Watercross National Tour will make a two-day stop in St. Augustine. Each day features more than six hours of action off the coast of the Atlantic Ocean, with the entire course visible from the shore of Vilano Beach.

The St. Augustine Cruisers 19th Annual Car & Truck Show will be held at the Classic Car Museum of St. Augustine. Open to all makes and models, registration is $25. Admission is free for spectators.

New in May 2021 is the first annual St. Augustine Food + Wine Festival showcasing some of the southeast's leading local chefs, guest celebrity chefs and hundreds of beverage tastings, along with live music. This culinary weekend celebration with celebrity guest chefs, winemakers and beverage experts in spirits and beers, for adults 21 and over only.

4. First Friday Art Walk

Date: May 7, 2021

first friday artwalk event

Join Art Galleries of St. Augustine the first Friday of every month from 5-9 p.m. for new exhibits, refreshments and live music at many participating galleries.

cheers beer glasses

Visit the Fountain of Youth Archaeological Park from 1-6 p.m. (general admission tickets); noon-1 p.m. (early admission VIP ticket holders) for this event. Proceeds benefit Keepers of the Coast and St. Augustine Lighthouse & Maritime Museum.

6. Yacht Rock Revue at The AMP

Date: May 15, 2021

The Yacht Rock Revue is everything the late ‘70s and early ‘80s should’ve been: massive sing-along soft rock hits, tight bell-bottom jeans, impeccable musicianship, polyester shirts, glorious vocal harmonies, sunglasses at night, breezy dancing and lots of sax.

Transport back to the 90’s with an all-day concert lineup featuring 1990s rapper and icon Coolio and Ken and Drew from Sister Hazel as well as Salt & Pine, Kapowski, Nerd Kill Overdrive, Bad Dog Mama, Ramona, Chillula, and more!

8. Matanzas 5K & Fun Run

Date: May 22, 2021

This race takes participants throughout downtown St. Augustine along the Matanzas River through the historic city and ends at Castillo Drive. The 5K begins at 8 a.m. and the free fun run begins at 9:15 a.m.


Hosted by the North Florida Bicycle Club, the Tour de Forts Classic is a one-day event designed for all road cyclists. The event begins at the St. Johns County Fairgrounds, and packet pick-up is available at 7:30 a.m. Ride through history past the Castillo de San Marcos to Fort Matanzas. The longer routes offer a ride through farmlands, the Palatka-to-St. Augustine State Trail and along the St. Johns River. Five distances are available: 26, 40, 55, 70 and 100 miles.

10. Music by the Sea - Free Concerts

Date: May 26 - September 29, 2021

This free weekly concert series at the St. Johns County Ocean Pier features a wide variety of musical genres from 7-9 p.m. Bring a beach chair or blanket along with a favorite beverage and get ready to dance. Starting at 6 p.m., dinner is offered as an option for concert goers. All dinners are priced at $10 or less. Concerts are from May 26 - September 29.

For more upcoming events in St. Augustine and Ponte Vedra, check out our events calendar.