How to Enjoy Labor Day Weekend in St. Augustine: 2025 Edition

by Kevin Howard

Labor Day weekend is the unofficial send-off to summer, and in St. Augustine, it’s a celebration of sunshine, history, and coastal charm. Whether you’re planning a quick getaway or you call the Nation’s Oldest City home, this guide will help you make the most of the long weekend with events, family fun, local dining, and beach tips you won’t want to miss.

1. Can’t-Miss Events This Labor Day Weekend

Umphrey's McGee at the St. Augustine Amphitheatre (8/31)
Active since 1997 and originating from South Bend, Indiana, Umphrey's McGee brings an eclectic mix of rock, funk, jazz, bluegrass, metal, country, and folk to the stage. Concert will be held at the Backyard Stage on Sunday, August 31st. Doors open at 5:30pm.

The Great St. Augustine Scavenger Hunt (8/30)
Test your knowledge, explore the city, and have fun at the Great St. Augustine Scavenger Hunt! This family-friendly event invites teams of 4–6 to solve clues, find landmarks, and complete missions throughout Historic Downtown St. Augustine. Admission is $200 per team and all proceeds benefit the Youth Crisis Center. Participants will gather at 10:00 a.m. in front of the Lightner Museum, where you'll learn the rules and sync your phone to their digital app. At 10:30, the app starts the scavenger hunt. Find St. Augustine's iconic landmarks, answer clues about our city, and earn points when you complete each quest. As the game moves along, the interactive app displays how your team ranks compared to the others. The team with the most points wins. The top three teams share some of the treasure with cash prizes: $500.00 for 1st place, $400.00 for 2nd place, and $300.00 for 3rd place.

2. Family-Friendly Activities Everyone Will Love

St. Augustine Alligator Farm – From giant gators to exotic birds and the thrilling Crocodile Crossing zipline, this is a kid favorite.
Castillo de San Marcos – Step back in time with live reenactments and breathtaking bayfront views.
Pirate & Treasure Museum – A fun way for kids to explore history while hunting for treasure.

3. Beach Access Tips for the Holiday Rush

Labor Day is one of the busiest beach weekends of the year — but with the right planning, you can skip the stress:

Arrive Early – Parking fills up fast at St. Augustine Beach, Vilano, and Anastasia State Park. Plan to arrive before 9:00 AM for the best spots.
Consider Lesser-Known Entrances – Crescent Beach, Guana State Park and the southern end of Vilano tend to be less crowded.
Check the Tides – Low tide means more beach space, ideal for families and games.
Beach Driving Permits – If you have a 4x4, driving on the sand can be a great way to find your own slice of paradise (available at select beach access points). You must purchase a beach pass to drive onto the beach ($10 or $5 for active military).

4. Best Restaurants for Your Long Weekend

Seafood by the Water:

St. Augustine Fish Camp – Relaxed harborfront restaurant featuring local seafood specialties with a southern flair.
Aunt Kate’s – Relaxed dining on the Intracoastal with sunset views.

Casual Coastal Eats:

Beachcomber St. Augustine – A casual beachfront cafe for breakfast, lunch & dinner served indoors or at duneside picnic tables.
Salt Life Food Shack – Fun atmosphere, rooftop seating, and a great poke bowl.

Historic Downtown Favorites:

Columbia Restaurant – Spanish-Cuban flavors in a stunning historic setting.
Catch 27 – Local seafood and seasonal plates in the heart of downtown.

Morning Coffee Runs:

The Kookaburra – Australian-inspired coffee and savory pies.
DOS Coffee & Wine – Craft coffee and fresh pastries.
Flamingo Coffee Bar - Brand new coffee shop on Anastasia Island near the Bridge of Lions serving coffee, food, beer and wine.

Make the Most of Your Holiday in the Oldest City

Labor Day weekend in St. Augustine is about savoring the last rays of summer — from sandy toes to sunset cocktails. Plan ahead, pack your sunscreen, and leave room in your schedule for a little spontaneity.