2025 Pin Up Paws Auction
2025-10-22, 2025-10-23, 2025-10-24, 2025-10-25, 2025-10-26, 2025-10-27, 2025-10-28, 2025-10-29 and 3 more dates | Online
2025 Pin Up Paws Auction
The St. Augustine Humane Society is kicking off its’ 15th Annual Pin Up Paws Auction. This community fundraiser supports pets and families in Northeast Florida!
Online, the auction begins on September 29 and runs through November 1, 2025. It features local dining, entertainment, travel experiences, and unique gift packages.
The auction culminates with the Pin Up Paws Gala on October 23, 2025 at The White Room in downtown St. Augustine.
Proceeds benefit the St. Augustine Humane Society’s mission, which is to provide affordable veterinary care and resources that help prevent animal surrender and reduce pet overpopulation in the community.
Click the event website link to place your bids.

2026 Pin Up Paws Calendar Party
2025-10-23 18:00 - 21:30 (America/New_York) | The White Room, 1 King Street, St. Augustine, FL, 32084, United States
Join us for the 2026 Pin Up Paws (PUP) Calendar Party where “The Gilded Paw” calendar is revealed! Find out whose pet “won” the ‘Grand Masterpiece’ cover and whose is a celebrated portrait of the month.
When: Thursday, October 23, 2025 — 6:00pm-9:30pm
Where: The White Room
Enjoy a delicious dinner, complimentary wine, cash bar, music by the House Cats jazz quartet, silent auction, wine pull, photo booth, caricature artist, and a free copy of the 2026 A Gilded Paw calendar.
Free parking is available nearby at Trinity Parish Parking Lot.
Tickets: $135.00 per person | pricing per table also available
Click the event website link for all the de”tails” and to purchase your tickets. Tickets also available at the Front Desk of the Humane Society.
This event is the largest fundraising effort the Humane Society hosts each year. All of the money raised will directly benefit our lifesaving programs and resources which provide care to the pets who need it most.

St. Benedict the Moor Blues Fest 2025
2025-10-24 16:00 - 22:00, 2025-10-25 16:00 - 22:00, 2025-10-26 11:00 - 15:30 | St. Benedict the Moor Catholic Church, 86 Martin Luther King Jr. Avenue, St. Augustine, FL, 32084, United States
St. Benedict the Moor Blues Fest 2025
October brings us the annual St. Benedict the Moor Blues Fest 2025! Nestled in the heart of the historic district of Lincolnville.
If you enjoy the blues and good food, then St Benedict the Moor Blues Festival is for you! This popular, annual event features Rockin’ Blues music, food, beverages and games at one of St. Augustine’s historical sites. Don’t forget your lawn chairs!
Friday, October 24, 2025 — 4:00pm – 10:00pm
Saturday, October 25, 2025 — 4:00pm – 10:00pm
Sunday, October 26, 2025 — 11:00am – 3:30pm
Music Lineup
Friday, October 24
4:00pm-6:00pm — Ken Jensen Blues Ensemble
6:00pm-8:00pm — Duffy Bishop Band
8:00pm-10:00pm — No Filter Blues Band
Saturday, October 25
4:00pm-6:00pm — Gitlo – Thos. Lee
6:00pm-8:00pm — Hitman Blues Band
8:00pm-10:00pm — JW Gilmore & the Blues Authority
Sunday, October 26 (Gospel Blues Sunday)
9:15am — Arlie Mae Victory
9:45am-11:00am — Americana Gospel
11:00am-12:00pm — Rick Spence Jazz Combo
Cost: $7.00
What makes this festival even more special is its’ noble cause – all proceeds go towards restoring the historic St. Benedict the Moor rectory/church. Attend and support a significant piece of St. Augustine’s rich Catholic heritage!
Click event website link for all additional information and to purchase your admission and food tickets.

Rooted in Excellence Fall Harvest Dinner
2025-10-24 18:00 | Michael’s, 117 Vilano Road, St. Augustine, FL, 32084, United States
You are invited to the Rooted in Excellence Fall Harvest Dinner. This signature dinner series is in partnership with the Friends of James Beard Foundation and benefits Pie in the Sky Community Alliance.
Rooted in Excellence brings together acclaimed chefs, local farmers, and passionate supporters to celebrate our region’s culinary spirit while providing fresh, healthy food to low-income seniors in St. Johns County through Pie in the Sky’s essential programs.
When: October 24, 2025 — 6:00pm
Where: Michael’s Private & Main Dining Rooms … for an intimate gathering of 100 guests
Cost: $250.00 per guest … includes multi-course dinner, thoughtfully paired wines, and a portion supporting Pie in the Sky’s mission.
Click the event website link to purchase your ticket(s).

Jail Break 5K 2025
2025-10-25 08:00 | Old Jail, 167 San Marco Avenue, St. Augustine, FL, 32084, United States
Jail Break 5K 2025 & Halloween Costume Contest
All runners and walkers are welcome to participate in the annual Jail Break 5K – Saturday, October 25, 2025 — 8:00am. During the race, the traditional Jail Break 5K Halloween Costume Contest will take place. Run/walk in costume to win one of the cash prizes.
Course Info
“Escape” from the historic Old Jail in uptown St. Augustine, proceed through scenic Magnolia Avenue and over the Vilano Bridge to the Atlantic Ocean. Transportation via shuttle for all racers will be provided at the finish of the race back to the start.
There’s also a virtual option if you can’t “Escape” in person.
Race Info
Beautiful finisher’s medal, distinctive t-shirt, unique themed course, a Halloween costume contest, refreshments, and family fun! Availability and size of shirts only guaranteed to those who register by September 30, 2025.
Water stations at the start, 1 mile, 2 mile, and finish.
5K USATF Certified Course # FL17069TY.
Proceeds from the race will benefit INK! Investing in Kids. Our mission: To provide innovative programs and classroom resources to promote the academic success of St. Johns County public school students.
Entry Fee:
$30.00 — May 1 – June 30, 2025
$35.00 — July 1 – October 14, 2025
$40.00 — October 15 – October 24, 2025
$45.00 — October 25 – Race Day
$40.00 – Virtual Option
Click on the event website link to register and for all additional information.

Shrine Club Southern Fried Chicken Night
2025-10-31 16:00 - 19:00 | St. Augustine Shrine Club, 250 Brainard Drive, St. Augustine, FL, 32086, United States
Shrine Club Southern Fried Chicken Night
Join us at the St. Augustine Shrine Club on the last Friday of each month from 4:00pm-7:00pm (except November & December) for a delicious Southern Fried Chicken Dinner. Dinner consists of 3 pieces of southern fried chicken with two sides, corn bread, dessert and iced tea.
All-inclusive meal for only $14.00 per plate. Dine in or take out available. Cash or credit card accepted. An on-site ATM is available.
Thanks to people like you, Shriner’s have been able to help more than 1.4 million children reach their potential and lead more fulfilling lives, regardless of the families’ ability to pay. Drop a tip in our jar and all these monies go directly to our hospitals to help children in need.

Blue Jean Bash and Benefit 2025
2025-11-06 17:30 | The Tringali Barn at Heritage Farms, 7310 US-1, St. Augstine, FL, 32086, United States
Blue Jean Bash and Benefit 2025
Mark your calendars! It’s time for the 5th annual Blue Jean Bash and Benefit! Benefiting the Alpha Omega Miracle Home! Join them as they DREAM BIG!
When: Thursday, November 6, 2025 at 5:30pm
Where: The Tringali Barn
Enjoy a night of fantastic food as well as delicious desserts. There’s also a live auction and entertainment.
Dressy Denim Attire.
Click the event website link for additional information … including ticket prices. And, to purchase those tickets.

Whiskey, Wine & Wildlife Event 2025
2025-11-07 18:30 - 20:30, 2025-11-08 10:00 - 12:00, 2025-11-08 14:00 - 17:00, 2025-11-09 10:30 - 14:00
Whiskey, Wine & Wildlife Event 2025
Mark your calendars for November 7-9, 2025 for this annual event! W3 is a culinary weekend like no other blending food & drink lovers with the surrounding beauty of nature! Raising funds and awareness for Vilano Beach Main Street and the St. Augustine Alligator Farm Zoological Park.
Enjoy beverage tastings artfully combined with inspired cuisine from some of the South’s best chefs as well as local culinary superstars. And, education experts are on-hand Friday and Saturday, showcasing some fun, interactive programs with coastal wildlife, from alligators to reptiles.
Please Note: Attendees must be of legal drinking age or older to attend most events. No dogs or pets allowed.
Events are rain or shine and programs are subject to change without notice.
Event Info | Schedule:
Friday, November 7
* 6:30pm-8:30pm Dinner – Vilano A1A Soirée – Hyatt Place St. Augustine/Vilano Beach. A tasting event – indoors and out – with gourmet bites. Sample some of NE Florida’s best restaurants, live music and more. Guests receive souvenir glass for unlimited beer, wine and spirits tastings.
Saturday, November 8
* 10:00am – 12:00pm – Alligator Farm VIP Behind the Scenes Tour – St. Augustine Alligator Farm Zoological Park. Guests are treated to a guided, behind the scenes, private tour … with special access to several exhibits. A tour of the “Rookery” is also included where native herons, egrets, spoonbills, and wood storks can be seen. Private Wine & Cheese Reception at the conclusion. Rain or shine.
* 2:00pm – 5:00pm – W3 Main Event – Whiskey, Wine & Wildlife Block Party – Hyatt Place St. Augustine/Vilano Beach. All three of the W’s and much more including: culinary delights from the A1A Corridor – some of northeast Florida’s best * hundreds of unlimited varieties of beverage tastings (spirits, wines and beers) with a souvenir glass * live music * wildlife and educational demonstrations from St. Augustine Alligator Farm.
Sunday, November 9
* 10:30am-12:00pm & 12:15pm-2:00pm (2 seatings) – W3 Sunday Jazz Brunch at Pesca by Michael’s. Grand Finale Brunch. Indoor. Enjoy a generous array of chef-attended stations, offering elegant, seasonal fare; souvenir glass with unlimited beverage tasting stations, and live piano music by Jolie.
Satellite Parking/Shuttle Service Information
Old Town Trolley will be providing Free shuttle service making it the best and most hassle-free way to attend Saturday’s Main Event. Every 30 minutes to and from St. Johns County parks on A1A to Vilano Beach. The schedule is available on the festival website.
Click the event website link to purchase your tickets and for all additional details, including parking and shuttle information.

Community Yard Sale at Limelight Theatre
2025-11-08 08:00 - 12:00 | Limelight Theatre, 11 Old Mission Avenue, St. Augustine, FL, 32084, United States
Mark your calendars for the Community Yard Sale at Limelight Theatre! Benefiting the Backstage Boosters for the exciting things they have planned for the education students!
When: Saturday, November 8, 2025 — 8:00am-12:00pm
In fact, if you have any items you would like to donate, they are more than welcome. Any household items, clothing, furniture, and other things you can’t use but are willing to donate. Just drop them off at the Matuza Black Box on Friday November 7 from 3:00pm-6:00pm.

Life-Changing Chili Cook-Off
2025-11-13 18:00 - 21:00 | 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.
