How to Spend your Weekends in St. Augustine

Fall and Winter Events

Summer and Spring are presumed to be the hottest time to adventure in St. Augustine – the ocean is calm, the sun is warm, and school is out! Contrary to popular belief, the cooler side of the year, is just as fantastic! Each weekend this Fall and Winter, is one to look forward to, in fact!

Plenty of events, festivals, concerts and holiday festivities will take place, prompting us to create a calendar of our favorite weekend to-do’s! Of course the two most popular events in St. Augustine during this time of year are the Nights of Lights, and the Bed and Breakfast Holiday Tour – but have you heard of the Great Chowder Debate, or the Greek Festival? Get details for these activities, and many others, below!


There are four festivals happening in October,
basically your weekends will be nothing less than terrific.

Oct 7th, 9am-4pm
Oct 8th, 10am-3pm

The Datil Pepper Fall Festival is a large celebration for North Florida's favorite spicy pepper the Datil! On Saturday, from 11:00 am to 1:00 pm, there is a restaurant cook-off - chef's compete to make the best Datil based entree!
Greek Festival

Oct. 14th, 4pm-10pm
Oct. 15th, 11am-10pm
Oct. 16th, 11am-5pm

The Greek Festival, an annual St. Augustine festival, will teach you everything Greek! From free authentic music, dance lessons, rides, games and of course a large gathering of vendors with delicious Greek plates.
Kayak in St. Augustine

Oct. 21st, 10am-1pm

For four days in October, take a Free Kayak Trip along the Moultrie Creek and learn about the marsh ecosystem and history of St. Augustine waters. This free, three hour tour, is family-friendly and educational!
Ancient City Kids Day

Oct. 28th, 11am-3pm

The Ancient City Kids Day is a totally family-designed, free event! Activities and games are specifically designed for parent-child interaction, with an educational purpose as well. A great resource for combining a day of quality time, learning and fun.
St. Augustine Corn Maze

Oct 7th - Oct
29th 9a-4p daily

Cooper and Sykes Farm is located about 15 minutes south of St. Augustine. They host a few events beginning in October, including: duck races, hay rides, a 9-acre corn maze, and a vintage home decor tent sale!
Songwriter's Festival

Oct. 13th, 8pm
Oct. 14th, 12pm

This year kicks off the very first Songwriter's Festival in St. Augustine. The event will feature well-known, new and old, artists along with recently found talent! Musicians will also speak on the meaning of their songs, who they were written for, or about!
TrailMark Festival

Oct. 21st, 11am-3pm

The TrailMark Fall Festival & Open House is a free event during October and the first of its kind in St. John's County. Gather your family and friends, and head over for hot-air-balloon trips, pumpkin patches, rock climbing, a giant slide, and yummy Fall refreshments.
Burning Man Scarecrow

Oct 28th, 6pm-9pm

The Goulish BBQ and Burning Man Scarecrow is hosted by a local farm, Rype and Readi. The night is spent eating delicious BBQ favorites, playing games, and watching a roaring fire of scarecrows burn!


Thanksgiving, Light Up! Night, and a ton of
musicians to look forward to in November.
Do dull weekends exist in St. Augustine? No.
Pumpkin Chunkin'

Nov. 4th, 9am-11am

Rype and Readi’s Elkton farm is hosting a Brunch and Pumpkin Chunkin’ Festival this year that can be enjoyed by everyone in the family. The day will consist of a yummy Fall brunch, chucking old pumpkins via catapult, extreme kite-flying, bike tours, and of course a petting zoo!
Veterans Day Parade

Nov 11th, 10:45am - 3:30pm

The Veterans Day Parade is a wonderful celebration honoring the veterans, and active military of the United States of America. Church bells and a cannon blast will mark the start of the parade, following, are powerful groups of marchers such as; veteran and active duty units, ROTC groups, actors, and high school marching bands.
Light Up! Night

Nov. 18th, 4pm-2am

If you are in St. Augustine for Light Up! Night, the kick-off night for Lights of Nights, you are in for a super holiday treat. The Christmas tree in the Plaza de la Constitucion is lit – followed by a ten second countdown that illuminates thousands of holiday light-bulbs, decorating downtown.
Lindsey Stirling

Nov. 25th, Starts at 8pm

Work-off your turkey dinners and apple pies with a night spent dancing to the beats of Lindsey Stirling, at the Amphitheater. World violinist, Lindsey, is best known for her classic and electric combined style – a Christmas concert that will keep you on your feet.
Chowder Debate

Nov. 5th, 12pm-4pm

Does 100 unique blends of clam chowder all for the tasting, sound like your perfect afternoon? If so, the Great Chowder Debate is an event you must attend. To sum it up, it is the biggest chowder event and longest running chowder championship in the country with over 30 participating restaurants and 200 chowders to taste!
Ottmar Liebert

Nov 12th, 8pm-12am

End your Sunday at the Ponte Vedra Concert Hall unwinding to the easy-listening music of Ottmar Lieberts, lead-musicican, of Luna Negra. The Spanish-influenced music is appropriate after a day in St. Augustine, don’t ya think?
Wine & Carriage NoL

Nov. 19th, 6pm-9pm

Sunday the 19th, give St. Augustine’s Winter Wonderland a second glance. There are plenty of ways to tour the Old City that include a great view of the light display! A popular one is Wine & Carriage Ride!
Art Festival | St. Augustine

Nov. 25th, 10am-5pm | Nov. 26th, 10am-4:30pm

End Thanksgiving weekend at the Art Festival, on Francis Field. Browse the dozens of tents carrying local and professional artwork, jewelry, and pottery – this is a great opportunity to get started on your Christmas decorations with unique hand-crafted pieces.


St. Augustine turns into a Winter Wonderland this December.
Hot chocolate, VIP tours, parades and plenty to
do each and every weekend!
Christmas Parade

Dec. 3rd, 9am - 11:30am

Grab your camping chairs and celebrate the first days of December with the Christmas Parade. Enjoy a delightful breakfast downtown and digest your food with a front seat to St. Augustine’s favorite parade! Actors, cannons, and an olden day theme – this parade takes you back to the holidays during the 17th century.
B&B Holiday Tour

Dec. 9th, 10th, 11th, 12th, 13th
Times vary.

The Bed and Breakfast Holiday Tour is an absolute holiday treat, curtesy of the St. Augustine’s historic inns – featuring the best restaurants in our city! This year’s theme is, Coastal Christmas, prompting all the B&B’s to uniquely dress their inn for the occasion. Yummy food and great holiday decorations are calling your name this Coastal Christmas.
Seussified Christmas Carol

Dec. 15th/16th, 5pm
Dec. 17th, 11am

Limelight theater presents a Seussified Christmas Carol, a Dr. Seuss inspired tale! A fantastic show for families - look forward to seeing special guests: binka bird geese, Bed-Headed Fred and Timmy Loo Ho!
Dressing Downton Exhibition

Dec. 23rd, 9am-5pm

The Lightner Museum, housed in the former Alcazar Hotel which was built by Henry Flagler in 1888, is a St. Augustine favorite. From October 4th to January 7th, the Dressing Downton Exhibition has over 30 of the costumes that actors wore, on display. The gallery will actually stand in the Ballroom of the Lightner Museum, an appropriate location, I’d say!
Uptown Saturday Night

Dec. 30th, 5pm - 8pm

Stroll San Marco Ave., in downtown St. Augustine! On the first Saturday of every month, the galleries and shops of San Marco join to host “Uptown Saturday Night”, a local favorite! Find unique art and shop for your New Year’s Eve outfit!
Tour of Homes

Dec. 3rd, 12pm - 5pm

The Tours of Homes event, is hosted by the Garden Club, and a look inside seven private homes all of which were built in the 1800’s. The homes are decorated head-to-toe and the theme this year is “Christmas in the Flagler Era.” After the tour, sip tea while browsing the Unique Boutique – a Garden Club special.
St. Aug VIP Tour

Fri/Sat from Nov. 24th - Jan. 27th
Departs at 6:30pm

As Christmas nears there is a good chance that one of two things is on your mind: holiday lights and hot chocolate. Enjoy them both at the VIP Nights of Lights tour – the weekend before Christmas. The tour is 1.5 hours of a fun and educational way to experience St. Augustine during the famous lightshow!
The Nutcracker

Dec. 17th, 130pm & 7pm

As Christmas nears, partake in the nation-wide tradition of watching the Nutcracker on stage! The St. Augustine Ballet will perform its annual holiday show with local celebrities, dancers and artists. This is also a great opportunity to take in Flagler College’s historic architecture!
Old Town Trolley Tour


Is there a more appropriate time to experience Nights of Lights than on Christmas Eve? I don’t think so! Take one more tour throughout the city by Old Town Trolley! Spend the night singing Christmas Carols with strangers and sipping on hot chocolate.
Beach Blast Off

Dec. 31st, 4pm - 10pm

Celebrate New Year's Eve at the Beach Blast Off! Pack up your family and friends and head to St. Johns County Pier Park for face-painting, a mechanical bull, a rock wall, and over 20 different food vendors. Fireworks will be set off over the ocean at 8:30pm. See ya then!

Happy Weekends Y’all!

St. Augustine Historic Inns


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Synthia Nadal
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