2018 Fall Events & Festivals


Sept. 1-2, Sept. 8-10, Sept. 15-17, Sept. 22-24: The Sing Out Loud Festival, the largest free music festival ever held in St. Johns County, returns for three weekends this September — Sept. 8-10, Sept. 15-17, and Sept. 22-24. Hundreds of performances will take place at multiple music venues around St. Augustine, Florida in an epic celebration of local, regional and national singers, songwriters and musicians. Go to singoutloudfestival.com to stay updated.


Sept. 9: The Great St. Augustine Wing Off & Sing Off  takes place from 11 a.m. to 3 p.m. Saturday, September 9 at the St. Augustine Beach Pier Pavilion, 350 A1A Beach Blvd., St. Augustine Beach. Who has the best Chicken Wings in town? Who’s the best Karaoke Singer in town? Bring your family and friends to enjoy a brand-new, fun-filled event! Local restaurants will compete for Best Wings and anyone can participate in the Karaoke Contest. Sign up in advance at: http://www.kids-bridge.org/donate-now.html Fee $10 to sing per contestant. Please provide your Name, Age, Phone Number, Category, Email, Song Choice not longer than 4 minutes. We will then follow up with you! You can also come the day of and sing! We will have 3 Judges to help you win your Category and also a People’s Choice Award for day of voting!  All proceeds benefit Kids Bridge Supervised Family Visitation Center.


Sept. 15: The Florida Heritage Book Festival features a FREE celebration of writers and book lovers, a full day of free literary events in the heart of the Ancient City. Meet best selling authors. Hear author’s presentations. Interact with one on one conversations with authors at book signings. Visit author’s marketplace and be creatively inspired. All presentations take place at the Ringhaver Center of beautiful and historic Flagler College. All September 15th Festival programs are free and open to the public with free trolley transportation to the Festival from the City Parking Garage. Go to fhbookfest.com/book-festival for details.


Oct. 6: The Pink Up The Pace 5K is a walk/run for breast cancer, with proceeds going to help local women with mammograms and treatment. On race day, warm-up begins at 7:20 a.m. on Francis Field, 29 W. Castillo Drive, near the downtown parking garage. A group survivor photo will take place a 7:30 p.m. next to the Pink Heals Fire Truck. The race begins at 8 a.m. at Francis Field on Saturday, Oct. 6. EXPO on Oct. 5 from 2:30-6:30 p.m. at First Coast Technical College, 2980 Collins Ave, St. Augustine. Fl 32084. The free event includes local community business vendors as they support Pink Up The Pace. They will be sharing information, raffling prizes and giving out gifts. To register online, go to www.pinkupthepace.com.


Oct. 6-7: The Datil Pepper Festival and Home and Garden Show will be held from 9 a.m. to 2 p.m. Saturday, Oct. 6; and from 10 a.m. to 3 p.m. Sunday, Oct. 7 at the St. Johns County Agricutural Center, 3125 Agricultural Center Drive, St. Augustine. Admission and parking is FREE. A variety of vendors, both inside and outside, will showcase unique items for sale. There will also be a food court, rain barrels for sale, and the always popular Master Gardener plant sale. Tours of the arboretum and community gardens will be conducted by our Master Gardeners throughout the weekend festivities. The festival’s famous Datil Pepper Cook-off will be held on Saturday only, from 11:30 a.m. to 1 p.m. Oct. 6. Local chefs will offer samples of their Datil-inspired cuisine. Guests can purchase taste tickets for $1 per ticket. Each ticket will give you an opportunity to sample one of the dishes and vote for your favorite in each category (appetizer and entree). Ticket sales for the cook-off begin at 11 a.m. and sell out quickly. Interested in being a vendor or a sponsor for the 2016 Datil Pepper Fall Festival? Go to stjohns.ifas.ufl.edu or call 904-209-0430 for more information.


Oct. 6-Nov. 4: Nine acres of a local farm becomes Sykes & Cooper Corn Maze each year — with live music, the maze, games such as a corn cannon, live animals and more at 5995 Brough Road in Elkton, just off State Road 207. Hours are 5 to 10 p.m. Fridays; 10 a.m. to 10 p.m. Saturdays; and 11 a.m. to 5 p.m. Sundays. Cost is $13 for ages 3 to 64; $11 for seniors and military with ID; and free for ages 2 and younger. Admission is CASH ONLY. Theme days are included, with Homeschool Day set for Oct. 5. Live music will be offered from 7 to 10 p.m. on certain Saturday nights. Go to www.sycofarms.com for more details.


Oct. 12-14: The St. Augustine Greek Festival celebrates all things Greek — food, music, dancing and heritage. The annual event is held at Francis Field, 29 W. Castillo Drive, downtown St. Augustine. Live music will be on stage throughout the weekend, with dance performances, a dance floor for the public, an outdoor marketplace, children’s activities and more. Admission is $5 for adults, and children age 14 and younger are admitted free with paying adults. Free admission for active military and first responders. Hours are 4 to 10 p.m. Friday, Oct. 12; 11 a.m. to 10 p.m. Saturday, Oct. 13; and 11 a.m. to 5 p.m. Sunday, Oct. 14. Go to www.stauggreekfest.com for more details.


Oct. 14: Feast on flavorful foods from locally-owned restaurants in the area at the 8th Annual St. Augustine Food and Wine Festival, set for noon to 4 p.m. Sunday, Oct. 14 at The River House, 179 Marine St., downtown St. Augustine. Savor Spirits from St. Augustine Distillery Co., sample over 100 wines, enjoy a beer garden, and bid on exciting silent auction items. See details at staugustinerestaurants.com. Proceeds will benefit the The Boys & Girls Club of St. Augustine.


Oct. 19-20: Hear live blues music from local performers and feast on food such as New Orlean’s gumbo, pulled pork, ribs, and desserts. Beverages include water, soda, and beer from Ancient City Brewing. Hours are 4-10 p.m. October 19 and 12-10 p.m. October 20 at St. Benedict The Moor Catholic Church, 86 MLK Blvd., in the Lincolnville area of St. Augustine. Admission is $5 and includes parking. See the schedule and stay updated here: http://www.stbensbluesfest.com/schedule/


  • Gene Johnson Road Blues Band
  • Night Hawks
  • Str8 Up
  • Parish Singers w/ Alexandra Richman Soltow
  • The Warehouse Boys (Willie Dixon)
  • John Allison Band
  • Tony Martin Band
  • JW Gilmore & The Blues Authority
  • Duffey Bishop Band


Oct. 27: The 21st Annual Ancient City Kids Day will be held from 11 a.m. to 3 p.m. Saturday, Oct. 28 at Francis Field , 29 W. Castillo Drive, downtown St. Augustine. The event is FREE for the public, and will include over 40 youth service agencies offering carnival style games and activities, arts and crafts, contests for kids, and live entertainment all day. Information about community resources will be available for parents. The only cost to the public will be for food or drinks. The event is a community outreach for Epic Behavioral Healthcare of St. Augustine. Go to epicbh.org


Nov. 9-10: The Haunted Flying Circus are a group time traveling performers from different cultures and periods of history — a motley mix of ghosts, immortals and mythical magic creatures. Performances are 8 p.m. Nov. 9-10 at the Willie Galimore Recreation Center, 399 Riberia Street, St. Augustine. Presale tickets are $13, and tickets are $15 at the door (cash only). Doors open at 7 p.m. Get tickets here.


Nov. 10: The 2018 Lincolnville Porch Fest will feature local musicians on front porches in the historic Lincolnville neighborhood in downtown St. Augustine. Stay updated at www.facebook.com/Lincolnvilleporchfest/


Nov. 16-18: The FIRST EVER 3-Day Music Festival set around Tiny Houses! This event takes places at the St. Johns County Fairgrounds, 5840 State Road 207, in Elkton, Florida — just miles from St. Augustine. Tiny homes, live music, artisans, vendors, food, a beer & wine garden, camping, and more! Get tickets here


Nov. 17-Jan. 31: The 24th Annual Nights of Lights opens on Saturday, Nov. 17 during Light-Up Night, an event that includes live music in the Plaza de la Constitucion, between King Street and Cathedral Place in downtown St. Augustine. The music will begin at 5:30 p.m., and the lighting ceremony will start at 6:30 p.m. Saturday, Nov. 17, 2018. Each year, former St. Augustine mayors gather to flip the switch during Light Up Night. The City of St. Augustine’s giant tree in the Plaza is lit first, then all the lights come on surrounding the area. Many families start the holiday season with this tradition — going to dinner downtown and and then watching as the lights are turned on. Nights of Lights, which includes more than 2 million lights on city buildings and businesses, continues through Jan. 31, 2016. Go to nightsoflights.com


Nov. 24-25: The 53rd Annual Fall Art & Craft Festival, hosted by the St. Augustine Art Association on Thanksgiving weekend, features more than 150 artists offering painting, pottery, jewelry, glassware, sculpture, fiber art, photography and mixed media. The even takes place at Francis Field, 29 W. Castillo Drive, downtown St. Augustine. Hours are 10 a.m. to 5 p.m. Saturday, Nov. 24; and 10 a.m. to 4:30 p.m. Sunday, Nov. 25. Go to staugustineartfestival.com for more details. 


St. Johns County Center for the Arts Musical Theatre students will perform Mamma Mia!, with more than 50 students on stage and behind the scenes. Directed by Jeff Dodd, the musical features ABBA’s hits and tell the hilarious story of a young woman’s search for her birth father.
Show times are 7 p.m. October 4-6 at St. Augustine High School Auditorium, 3205 Varella Ave., St. Augustine. Tickets are $10 for students, $15 for adults; available on Eventbrite or one hour prior to performances at the door.


  • 7 p.m. October 4-6
  • St. Augustine High School Auditorium, 3205 Varella Ave., St. Augustine


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