St. Augustine, FL | Oldcity.com

Life-Changing Chili Cook-Off
2025-11-13 18:00 - 21:00 (America/New_York) | The Tringali Barn at Heritage Farms, 7310 US-1, St. Augstine, FL, 32086, United States
Life-Changing Chili Cook-Off – A Rethreaded Event
Join us for an unforgettable evening that’s more than just chili! Not only can you can sample and judge the best local chili … you’ll enjoy complimentary bourbon and toffee tastings as well as live music for dancing to. And, there will be early holiday shopping opportunities and multiple raffles with exciting prizes throughout the night.
When: Thursday, November 13, 2025 | 6:00pm-9:00pm
Where: Tringali Barn
Every dollar raised directly supports survivors of human trafficking, helping them rebuild their lives through meaningful employment, career development, and vital support services.
Cost: $17.17
Click the event website link to purchase your ticket(s) and for all additional information.

Endless Summer 5K/10K 2025
2025-11-15 08:15 | Anastasia State Park, 300 Anastasia Park Road, St. Augustine, FL, 32080, United States
Endless Summer 5K/10K 2025
Be sure to mark your calendars! Don’s Friends Endless Summer 5K/10K 2025 is Saturday, November 15, 2025. It’s the 22nd Anniversary for Endless Summer Run and the 16th Anniversary for Don’s Friends 5K! Presented by Don’s Friends … hosted by Anastasia State Park.
Benefiting 2 Great Charities… Don’s FRIENDS and Friends of Anastasia!
Sign up early! Both runs sell out fast! There are also virtual options!
Course Info
10K Cross Country Run — Start time 8:15am
Begins near the Island Beach Shop and Grill a beach loop that is followed by a long wood deck, pavement, dirt roads, and soil through the east nature trail and hammock loop. Runners will return to the pavement and then another trail as they head to the marsh loop. The last leg of the run shoots the runners back down the main park road to the finish line at the Island Beach Shop and Grill.
5K Beach Run/Walk — Start time 8:15am
Also begins near the Island Beach Shop and Grill and is mostly on Anastasia State Park’s beautiful beach. It proceeds along the Ocean Front for 1.3 miles North, then turns back South on the Beach, then over the long boardwalk and along the road to the finish line also at the Island Beach Shop and Grill.
All runners/walkers will receive our FAMOUS Performance TECH T-Shirt featuring our full-color Turtle graphic. For 2025, we will also be giving a Beautiful Full Color Sublimated Bag Featuring our 2025 Turtle art. And … all runners will also receive a beautiful, LARGE Turtle finishers medal at the finish line.
0.0K Option — If you would like a T-shirt and to support the Foundation, there is a reduced rate for the shirt.
Click the event website link for registration fees, to register and for all additional information.

Festival Of Trees
2025-11-21 17:00 - 21:00, 2025-11-22 08:30 - 11:00, 2025-11-22 18:00 - 22:00, 2025-11-23 10:00 - 14:00 | St. Anastasia Catholic Church, 5205 A1A S, St. Augustine, FL, 32080, United States
5th Annual Festival Of Trees
Step into a Holiday Wonderland at the Festival of Trees! Guests will enjoy live music, holiday treats, and the chance to bid on beautifully decorated trees and wreaths. Best of all, the proceeds support local youth, men, women, and families experiencing homelessness.
Where: Anastasia Catholic Church Celebration Hall
When: Friday-Sunday, November 21-23, 2025
Festivities Schedule
Friday, November 21 — 5:00pm-9:00pm — Festive Night Market — Free Entry
Saturday, November 22
* 8:30am-11:00am — Pancake Breakfast with Santa, Storytime with Mrs. Claus, and cookie decorating — $20.00 per person
* 6:00pm-10:00pm — Elegant Jingle Ball Gala with holiday cocktails, hors d’oeuvres, music, and dancing — $150.00 per person
Sunday, November 23 — 10:00am-2:00pm — Final walk-through for silent auction filled with beautiful wreaths and trees.
The trees will be displayed during the entire weekend-long event and are donated by local businesses and organizations. You do not have to attend to bid as the auction will also be online.
Click the event website link for all the details and to purchase your tickets.

Shut Up and Run 5K 2025
2025-11-27 08:00 - 10:30 | Treaty Park, 1595 Wildwood Drive, St. Augstine, FL, 32086, United States
Mark your calendars for the annual Shut Up and Run X-C 5K Race!
When: Thanksgiving Day, Thursday, November 27, 2025 at 8:00am
Where: Treaty Park
Benefiting:
* St. Francis House – St. Johns County’s only privately funded homeless shelter
* Ancient City Road Runners – supporting local school running programs
* Don’s Friends – supporting local charities and helping others
Registration ends November 25, 2025 @ 11:20pm
Registration Fee: $35.00 Race Fee + $3.10 Sign-up Fee
Questions? Contact the race director at jim@donsfriend.com
For additional information and to register, click the event website link.

5th Annual Magic at Markland
2025-12-04 18:00 - 21:00 | Markland House, 102 King Street, St. Augustine, FL, 32084, United States
5th Annual Magic at Markland
Magic at Markland is one of the signature fundraiser events hosted by the Women of Vision Advisory Board. This magical holiday celebration includes: Live Music * Wine & Spirits * Culinary Bites * Silent Auction * Festive Photo Opportunities
When: Thursday, December 4, 2025 | 6:00pm-9:00pm
Where: the historic Markland House on the Flagler College campus
Cost:
* General Admission: $125.00
* VIP Admission: $175.00 (Includes seating, one raffle ticket, and a 30-minute Trolley Tour)
All proceeds from every Women of Vision event raises money that directly funds financial aid and educational opportunities for young students attending Flagler College. These awards relieve financial burdens and empower them to excel in their studies while pursuing research, internships, and service work. Combined, these ventures prepare them for high-impact social engagement and vibrant, successful careers upon graduation.
Click the event website link to purchase your tickets and for all additional information.

Santa Suits on the Loose 5K 2025
2025-12-13 08:00 | St. Augustine Beach Pier, 350 A1A Beach Blvd, St. Augustine, 32080
Get in the Holiday spirit and join us for the 14th annual Santa Suits on the Loose 5K 2025 – Walk | Jog | Run! Everyone is encouraged to dress in their best holiday spirit. Have some fun for a worthy cause during this Annual event!
When: Saturday, December 13, 2025 at 8:00am
Where: St. Augustine Beach Pier
All proceeds benefiting St. Augustine Youth Services (SAYS).
Choice of Santa Suit or race themed T-Shirt. Santa Suits limited to first 50 registrants.
Team Challenge — receive bragging rights and a traveling trophy for registering the most participants as a team!
Proceeds help provide normal experiences to residential foster kids and those with a mental health diagnosis and non-traditional families, especially during the Holiday season.
Cost: $30.00 (Please Note: price increases after July 24, 2025 at 11:59pm)
Click event website link to register and for all additional information.

Jimmy Jam BBQ Slam 2026
2026-01-10 10:00 - 18:00 | St. Johns County Fairgrounds, 5840 State Road 207, Elkton, FL, 32033
Jimmy Jam BBQ Slam 2026
Be sure to head to the St. Johns County Fairgrounds for the 10th Annual Jimmy Jam BBQ Slam! The Largest BBQ Competition in North Florida! Featuring the best pitmasters from across the nation competing at either the Backyard or Pro level.
When: Saturday, January 10, 2026 — 10:00am-6:00pm
Honoring James Wray and embodying everything Jimmy loved…helping others, BBQ and cars. Every dollar raised goes to help meet the needs of people throughout the community needing a helping hand!
KCBS BBQ Competition * Chili & Chowder Cookoff Car Show * Lumberjack Show * Cornhole Competition * Live Music * Local Vendors * Kids Zone * Great Food * Raffle … and More!
Event Schedule
10:00am — Gates Open | Free Parking
10:00am — Sign-up for Cornhole Tournament
11:00am & 2:00pm — Paul Bunyan Lumberjack Show (free)
11:00am-3:00pm — Chili & Chowder Cook-Off — Purchase $1.00 Tasting Tokens to sample delicous chili and chowder. Every $10.00 spent gets you 1 Voting Token.
2:00pm-4:00pm — Barbeque Tastings. Purchase $1.00 Tasting Tokens to enjoy a variety of delectable BBQ. Every $20.00 spent gets you 1 Voting Token to help crown the BBQ champion.
Tickets:
General Admission — $15.00 (Ages 10 and under Free)
VIP Experience — $50.00+ — Receive 5 Free Chili Tasting Tickets & 5 Free BBQ Tasting Tickets, 1 Free Beer. VIP Bathroom Access & VIP Parking.
Pet-friendly … However, they must be leashed at all times.
Click the event website link for all additional details. That includes competition information, event registration information and more. And to purchase your tickets.
Image used is from event website.

The Foundation 5000 2026
2026-01-17 08:00 - 11:00 | UF Health Flagler Hospital, 400 Health Park Blvd., St. Augustine, FL, 32086, United States
Don’t miss the 3rd annual The Foundation 5000 … hosted by UF Health St. Johns Foundation. Supporting the UF Health St. Johns Care Connect Mobile Outreach Clinic and its’ ongoing efforts to provide medical assistance to our community’s most vulnerable populations.
Have your family and friends join you for a day filled with fitness, philanthropy and community spirit! Custom race T-Shirt and Finisher’s Medal, Custom Awards, Chipped-Timed Race, and More!
When: Saturday, January 17, 2026 at 8:00am
Where: 400 Health Park Blvd.
Schedule of Events:
8:00am — Start Time
9:00am-11:00am — Post-Race Fair .. including:
9:15am — Awards Ceremony
Cost: $20.00 through December 31, 2025 at 11:59EST – then price increases.
Click the event website link to register and for additional details.

Pub Crawl Fundraiser for Betty Griffin
2026-01-17 17:00 - 23:00
Wear It More Than Once Pub Crawl Fundraiser for Betty Griffin
Break out the white dress, bridesmaid dress, or any other fun dress/outfit you want to wear again for a good cause! Attendees should wear wedding attire including a wedding dress, bridesmaid, or groomsmen attire … or other wedding related ensemble.
This is a ridiculously fun pub crawl on Anastasia Boulevard, just over the Bridge of Lions on the island in St. Augustine. You simply can’t miss this!
New location this year and 4 stops planned!!!
Participating pubs:

#1 Check in at Flamingo Coffee, 322 Anastasia Boulevard
#2 Old Coast Ales, 300 Anastasia Boulevard
#3 Coming Soon
#4 Hornski’s Brewing Co., 100 Anastasia Boulevard
Tickets: $50.00 … and only 50 tickets are available! Tickets do not include drink or other purchases. Ticket link coming soon! Keep checking the event website link.
100% of ticket sales are donated to Betty Griffin Center.
Image used is from a past fundraiser event.

2026 Matanzas 5000
2026-01-24 08:00 | Francis Field, 25 W. Castillo Drive, St. Augustine, FL, 32084, United States
2026 Matanzas 5000
Join the Ancient City Road Runners on Saturday, January 24, 2026 for the 46th annual Matanzas 5000! Florida’s fastest 5K on a USATF-certified 3.1-mile course through scenic, historic St. Augustine.
Proceeds benefit youth running programs in St. Johns County high schools and middle schools as well as the Florida School for the Deaf and Blind.
The start line is located at 29 West Castillo Drive next to Francis Field. The race runs along the beautiful bayfront in downtown St. Augustine, winds through historic neighborhoods, past Flagler College, finishing on Castillo Drive near Francis Field.
Race Start: 8:00am
Click on the event website link for all additional information and to register.

Character Counts! 6K/3K Run/Walk 2026
2026-02-07 09:00 - 11:00 | Palencia Elementary School, 355 Palencia Village Drive, St. Augustine, FL, 32095, United States
Character Counts! 6K/3K Run/Walk 2026
Mark your calendars! The annual Character Counts! 6K/3K Run/Walk is on February 7, 2026 at Palencia Elementary School.
Start Time: 9:00am for both the 6K Run/Walk and 3K Run/Walk
Professionally timed and scored by Hasselmania Productions.
Awards are given in several categories for both 6K and 3K runners.
Entry Fees: 6K/3K Run/Walk – $30.00 prior to January 1 | $35.00 January 1 to February 6 | $40.00 on Race Day
Click on the event website link for all additional information and to register.

Lighthouse 5K & Fun Run 2026
2026-02-21 08:00 | St. Augustine Lighthouse & Maritime Museum, 100 Red Cox Road, St. Augustine, FL, 32080, United States
Lighthouse 5K Run/Walk & Fun Run 2026
Mark your calendars! The 42nd annual Lighthouse 5K Run/Walk & Fun Run is on February 21, 2026. Presented by the Junior Service League of St. Augustine (JSL).
Times:
5K Run/Walk — 8:00am-10:00am
Fun Run — 9:00am-10:00am
There’s also a Virtual option if you’re not able to be there in person.
Hosted by RaceSmith, Inc., the Lighthouse 5K is a chipped race that serves as a qualifier for the famed Gate River Run. The Fun Run is a wonderful treat for the little runners. Both begin and end at the Lighthouse.
Don’t miss the Awards Ceremony afterwards on the grounds of the Lighthouse!
Post Run Activities
Immediately After 5K & Fun Run — Free of charge! Kids’ Activities … Face Painting, Arts & Crafts, and More * Climb to the top of the Lighthouse for the best view in all of Northeast Florida … for Free!
Proceeds from the Lighthouse 5K Run/Walk & Fun Run benefit numerous Junior Service League service projects and as well as provide financial support for local non-profit organizations in our community.
Click on the event website link to register and for complete details, including registration fees.
Image used is from Lighthouse 5K Facebook.

Fight Night for Charity
2026-02-26 17:00 | St. Augustine Amphitheatre, 1340C A1A South, St. Augustine, FL, 32080, United States
St. Johns County Fight Night – First Responders Boxing for Charity!
Come out to the St. Augustine Amphitheatre to support your local Deputies and Firefighters as they leave it all in the ring! While supporting your local heroes, you can contribute to a much larger cause … benefiting the children in our community!
Two special charity projects will receive assistance stemming from this event. They are:
* Diamond of Dreams — a new build project providing a ball field and a playground for children with special needs
* Special Olympics Florida — focuses on our local athletes with intellectual disabilities participating in various sports
When: Thursday, February 26, 2026 | First Bell Rings at 6:00pm Sharp
The boxing ring will be placed in the pit area, so every seat will be fantastic! There will be VIP seating options, food and drinks,
Fight Night merchandise and more.
The main events consist of members of SJSO, SJCFR, and SAFD battling for the belt and annual title. These fighters have shown commitment and devotion to the event in their off time while still serving the community in fire trucks, patrol cars, and our jail.
The fights will be three rounds, one minute each, with a one-minute interval.
Doors open 5:00pm | Fights begin 6:00pm
Tickets: prices vary
Note – there is a Black Friday only sale with discounted rates.
Click the event website link to purchase your tickets!

2026 Raptor Run 3K
2026-03-01 08:00 - 10:00 | St. Augustine Alligator Farm Zoological Park, 999 Anastasia Blvd., St. Augustine, FL, 32080, United States
Runners/walkers … head to the St. Augustine Alligator Farm on Sunday, March 1, 2026 for the Raptor Run 3K — 8:00am-10:00am. Designed for all ages! Help save native wildlife species in Florida!
Start at the Alligator Farm, continue through the Davis Shores neighborhood, and finish back at the Alligator Farm.
Water stations will be at the Start, 1 mile, and Finish. Digital time clock viewable at the Finish.
3K USATF Certified Course # FL20012JK
Cost: $35.00 | Price increases after January 18, 2026.
Registration will be capped this year at 500 entries.
Beneficiary: to be determined – local wildlife conservation organization
Free parking for the entire day at the Alligator Farm.
Click the event website link to register and for all additional info.

Vilano Bridge 5K & 10K Run 2026
2026-03-28 08:00 | Vilano Beach Community Center and Park, 120 Meadow Ave, St. Augustine, 32084, United States
Vilano Bridge 5K & 10K Run 2026
Mark your calendars for the Vilano Bridge 5K & 10K Run on Saturday, March 28, 2026 at 8:00am …. 1-mile Fun Run immediately following. Celebrating 28 years!
Start the scenic 5K & 10K Run at the Vilano Beach Community Center and Park. Wind your way through the Vilano Beach community, crossing over the scenic Vilano Bridge with its’ incredible views. The 10K continues to wind through the Florida School of the Deaf and Blind grounds.
Both finish at the North Shores Community Park where there is a post-race celebration with food, music, beer, drawings, and Fun!
Click on the event website link for registration fees, to register, and for additional information. T-shirts for those who register prior to March 13, 2026.
Your registration will go to supporting important projects in the Vilano and North Shores communities and the Florida School for the Deaf and Blind.

Run For Peace 5K 2026
2026-04-04 08:00 | St. Augustine Beach Pier, 350 A1A Beach Blvd, St. Augustine, 32080
Betty Griffin Center Run For Peace 5K 2026
Join us on Saturday, April 4, 2026 for the 12th annual Betty Griffin Center Run For Peace 5K. The race course is fast, flat and fun!
The 5K begins at 8:00am at St. Augustine Beach / St. Johns County Pier Park and travels through scenic beach neighborhoods back to the Pier. Water stations will be at 1 and 2 mile marks and at the finish.
A virtual run option is also available for those not able to make it in person.
Thank you for joining with us in supporting our vision of peace at home …. and the world! All proceeds raised go towards helping Betty Griffin Center save the lives of domestic and sexual abuse victims in St. Johns County.
Click the event website link to register and for all additional information, including cost.

Race to the Taste 5K 2026
2026-04-12 10:30 | St. Augustine Amphitheatre, 1340C A1A South, St. Augustine, FL, 32080, United States
Race to the Taste 5K 2026
Join us for the the only 5K in St. Augustine tied to an extraordinary culinary event … the Taste of St. Augustine … a culinary event featuring delicious local food and great music.
Everyone can enter …. individuals, families (bring the kids and strollers), walkers, and joggers. The 5K cuts through historic Anastasia State Park and surrounding neighborhoods! The race is meant for everyone!
When: Sunday, April 12, 2026 starting at 10:30am.
Where: Starting and ending at The St. Augustine Amphitheatre
Register for the Race and receive one Free Admission to the Taste of St. Augustine! Relax before and after the race and enjoy live music on the Amphitheater Front Porch stage, along with sampling over 20 local restaurant’s signature dishes! (“Taste Tickets” available for purchase at the event).
Proceeds benefit EPIC Behavioral Healthcare, a nonprofit serving St. Johns County families since 1973.
For all the details and to register, click on the event website link.
Image used is from EPIC’s website.

Taste of St. Augustine 2026
2026-04-12 11:00 - 16:00 | St. Augustine Amphitheatre, 1340C A1A South, St. Augustine, FL, 32080, United States
Taste of St. Augustine 2026
Mark your calendars for the 29th annual Taste of St. Augustine! Come enjoy great food and music at this popular annual event benefiting EPIC Behavorial Healthcare! Highlighting the culinary heritage and culture of St. Johns County by showcasing new restaurants and established favorites.
When: Sunday, April 12, 2026 | 11:00am-4:00pm
Where: St. Augustine Amphitheatre
Sample delicious dishes from more than 20 local food trucks and restaurants. Be sure to vote for your favorite to win the People’s Choice Award! You’ll receive a map showing participating restaurants, their location, and the dish(es) they’re serving.
Enjoy live entertainment! Kids can have fun in the Kids Zone!
Participants from the Race to the Taste 5K start and end at the Amp where they can relax and enjoy the delicious food afterwards.
Ticket Information
General Admission: $10.00 | Children are free
VIP Tickets also available
Click the event website link for all additional information.
Image used is from EPIC’s website.

Hometown Hero's Ride 2026
2026-04-18 08:30 - 15:00 | Adamec Harley-Davidson of St. Augustine, 380 Outlet Mall Blvd., St. Augstine, FL, 32084, United States
Join us for the 5th annual Hometown Hero’s Ride, starting and ending at Adamec Harley-Davidson of St. Augustine. Police escorted, the ride honors/benefits local families of military, law enforcement, and first responders.
When: Saturday, April 18, 2026
* Registration — 8:30am-10:30am
* Kick Stands Up — 11:00am
* Food, Vendors, Music, Raffles, and More — 12:00pm-3:00pm
Organized in 2022, each year a Northeast Florida family is selected to honor and benefit through our partner, Builders Care, and other partnering nonprofits that serve veterans, military personnel, emergency responders, and law enforcement. The 2026 Honoree is yet to be determined.
Cost: $25.00 per bike**
**The first 300 registered bikes include ride T-shirt. Lunch provided upon return.
Through co-ordination with the Veteran Enforcers Motorcycle Association (VEMA) St. Johns County Chapter, Adamec Harley Davidson of St. Augustine, and Northeast Florida Builders Association’s (Builders Care).
Click the event website link for all additional information.
The image used is from the website.
