Downtown DeLand Events — Music, Markets & Festivals
Quick answer: Downtown DeLand hosts events year-round — live music, the monthly art walk, farmers and artisan markets, seasonal festivals, and shows at the historic Athens Theatre. Browse what's coming up below, grouped by month.
Upcoming events
October 2026
America 250 at De Leon Springs State Park
9:00 AM – 5:00 PM EDT
Downtown DeLand
As part of Adventures Unbound, we are celebrating America 250 by inviting you to experience the places that define America’s story through nature, adventure, and time well spent outside. At De Leon Springs State Park we are offering 25% off paddle craft rentals (kayaks, canoes, stand-up paddleboards) through December 31, 2026. Valid on walk-up bookings only. Mention promo code AMERICA250 at the b…
Event detailsAmerica 250 at Hontoon Island State Park
9:00 AM – 4:00 PM EDT
Downtown DeLand
As part of Adventures Unbound, we are celebrating America 250 by inviting you to experience the places that define America’s story through nature, adventure, and time well spent outside. At Hontoon Island State Park, we are offering 25% off small-boat rentals through December 31, 2026. Book your tour at and use promo code AMERICA250 at checkout.
Event detailsAmerica 250 at Blue Spring State Park
10:00 AM – 12:00 PM EDT
Downtown DeLand
As part of Adventures Unbound, we are celebrating America 250 by inviting you to experience the places that define America’s story through nature, adventure, and time well spent outside. Blue Spring State Park is offering a 25% discount on a 2-hour narrated cruise along the St. Johns River. Enjoy historical insights and spot abundant local wildlife, including birds, manatees (during manatee seaso…
Event detailsFamily Bingo Night @ Gators Dockside Deland
6:00 PM – 8:30 PM EDT
1788 South Woodland Boulevard, DeLand
Family Bingo Night at Gators Dockside of DeLand! Grab the kids, bring the grandparents, and get ready for 6 rounds of bingo packed with laughs and family-friendly fun. It’s FREE to play, easy to jump in, and the perfect excuse for a relaxed night out together!
Event detailsAmerica 250 at Hontoon Island State Park
9:00 AM – 4:00 PM EDT
Downtown DeLand
As part of Adventures Unbound, we are celebrating America 250 by inviting you to experience the places that define America’s story through nature, adventure, and time well spent outside. At Hontoon Island State Park, we are offering 25% off small-boat rentals through December 31, 2026. Book your tour at and use promo code AMERICA250 at checkout.
Event detailsAmerica 250 at De Leon Springs State Park
9:00 AM – 5:00 PM EDT
Downtown DeLand
As part of Adventures Unbound, we are celebrating America 250 by inviting you to experience the places that define America’s story through nature, adventure, and time well spent outside. At De Leon Springs State Park we are offering 25% off paddle craft rentals (kayaks, canoes, stand-up paddleboards) through December 31, 2026. Valid on walk-up bookings only. Mention promo code AMERICA250 at the b…
Event detailsAmerica 250 at Blue Spring State Park
10:00 AM – 12:00 PM EDT
Downtown DeLand
As part of Adventures Unbound, we are celebrating America 250 by inviting you to experience the places that define America’s story through nature, adventure, and time well spent outside. Blue Spring State Park is offering a 25% discount on a 2-hour narrated cruise along the St. Johns River. Enjoy historical insights and spot abundant local wildlife, including birds, manatees (during manatee seaso…
Event detailsTuesday Pokémon at The Gamers Guild
4:00 PM – 8:00 PM EDT
Downtown DeLand
Pokémon at The Gamers Guild every Tuesday 4 PM–8 PM Catch • Trade • Battle Bring your deck, make some trades, and get some games in with the community. Working on a new build? Test it out. Looking to trade or meet other players? There’s always something going on. New to Pokémon or just getting back into it, this is an easy night to jump in and find a game. See you at the tables. #TheGamersGuild #…
Event detailsLUNA: A Gothic Feast and Spectacle
6:00 PM – 9:00 PM EDT
Downtown DeLand
For one extraordinary evening, Indiana Avenue will close to traffic and become the setting for LUNA: A Gothic Feast and Spectacle. On October 21, guests will dine outdoors in the heart of historic downtown DeLand for an immersive evening of food, wine, performance, and theatrical spectacle—all in support of the Athens Theatre and the launch of its endowment fund. Presented in collaboration with C…
Event detailsTrivia Party - Persimmon Hollow Brewing Co
8:00 PM – 9:00 PM EDT
111 West Georgia Avenue, DeLand
TRIVIA NIGHT AT PERSIMMON HOLLOW! Every Wednesday at Persimmon Hollow Brewing Co in DeLand! Test your knowledge, sip amazing craft beer, and compete for awesome prizes! FREE to play! Family friendly! Great prizes! Cold drinks all night! Grab your smartest friends and join us for the best Wednesday night in DeLand! See you at Persimmon Hollow! Every Wednesday Trivia Night FREE Entry #PersimmonHoll…
Event detailsGeneral Knowledge Trivia @ Blue Springs Brewing
6:00 PM – 8:00 PM EDT
Downtown DeLand
Think you know a little bit about everything? Come prove it at General Knowledge Trivia—fun questions, big laughs, and awesome prizes are waiting!
Event detailsSAK Comedy Lab (DeLand YMCA Fundraiser)
7:00 PM – 9:00 PM EDT
Downtown DeLand
Come enjoy a night of laughter with SAK Comedy Lab! Since 1991, their professional ensemble of improve actors has been entertaining audiences with their unique brand of live, improvised comedy. They take your suggestions and create characters, scenes and songs on the spot. Their comedy is sharp, fun and suitable for the entire family. Comedy for a Cause is a special event sponsored by the DeLand…
Event detailsTrivia Party - Gator's Dockside DeLand
7:00 PM – 9:00 PM EDT
Downtown DeLand
Get your game face on, DeLand! Thursday nights at Gator’s Dockside are about more than just great wings—they’re about proving you’re the smartest person at the table (and maybe the whole restaurant). Whether you’re a history buff, a pop-culture pro, or just really good at guessing, grab your crew and meet us for Weekly Trivia! The Details: Where: Gator’s Dockside DeLand When: Every Thursday @ 7:0…
Event detailsGeneral Knowledge Trivia @ Cocky Rooster Cafe & Grill
6:30 PM – 8:00 PM EDT
Downtown DeLand
Start your weekend with a brainy battle and some seriously good eats as we take on everything from pop culture to sports to totally random fun facts. Grab a drink, round up your trivia crew, and see who’s got what it takes to rule the roost.
Event detailsFamily Bingo Night @ Gators Dockside Deland
6:00 PM – 8:30 PM EDT
1788 South Woodland Boulevard, DeLand
Family Bingo Night at Gators Dockside of DeLand! Grab the kids, bring the grandparents, and get ready for 6 rounds of bingo packed with laughs and family-friendly fun. It’s FREE to play, easy to jump in, and the perfect excuse for a relaxed night out together!
Event detailsRocky Horror Picture Show with Shadow Cast
8:00 PM – 10:00 PM EDT
Downtown DeLand
Don your leather jacket, corset, and fishnet tights—because DeLand Pride and the Absent Friends are bringing the cult classic The Rocky Horror Picture Show back to the Athens Theatre after much “antici…pation.” Experiencing “Rocky” for the first time? Or maybe the 100th? We invite you to come do “The Time Warp” again! The fun begins before the film with live drag performances from DeLand Pride (b…
Event detailsNovember 2026
First Tuesday Volunteer Trail Team at D Ranch Preserve
9:30 AM – 12:00 PM EST
Downtown DeLand
Join us on the first Tuesday of every month for a hands-on volunteer morning at Conservation Florida’s D Ranch Preserve! We’ll spend the morning maintaining our trail system to keep it safe, accessible, and beautiful for everyone who visits. Volunteer Activities May Include: - Widening and maintaining nature trails - Trimming overgrown corners and cutting back brush - Clearing fallen branches and…
Event detailsMagic Ann – The Heart Tribute
7:30 PM – 9:00 PM EST
Downtown DeLand
Magic Ann – The Heart Tribute Featuring Jade as Ann Wilson Magic Ann – The Heart Tribute is a powerful, high-energy celebration of one of rock’s most iconic bands, Heart . This electrifying tribute captures the spirit, soul, and soaring vocals that made songs like “Barracuda,” “Crazy On You,” “Alone,” and “These Dreams” timeless classics. Front and center is Jade, lead singer of Ticket to the Moo…
Event detailsThe Dirty Doors: a Tribute to The Doors
7:30 PM – 9:30 PM EST
Downtown DeLand
The Dirty Doors celebrate the energy, excitement, and passion of the timeless music of Jim Morrison and The Doors like no other tribute band. With an intoxicating sound, provocative and uncompromising songs, and the mesmerizing power of singer Jim Morrison, The Doors had a transformative impact on popular music and popular culture. Based in Atlanta, The Dirty Doors faithfully recreates the magic…
Event detailsVolusia County Veterans Day Parade
9:30 AM – 3:00 PM EST
Woodland Blvd.
Honor those who have served our nation at this heartwarming annual parade.
Event detailsA Christmas Story – The Musical!
7:30 PM – 9:30 PM EST
Downtown DeLand
Book by Joseph Robinette Music and lyrics by Benj Pasek and Justin Paul Based on the motion picture A Christmas Story distributed by Warner Bros., written by Jean Shepherd, Leigh Brown and Bob Clark, and upon In God We Trust: All Others Pay Cash written by Jean Shepherd. Produced with permission of Warner Bros. Theatre Ventures and Dalfie Entertainment. You’ll shoot your eye out! A Christmas Stor…
Event detailsA Christmas Story – The Musical!
7:30 PM – 9:30 PM EST
Downtown DeLand
Book by Joseph Robinette Music and lyrics by Benj Pasek and Justin Paul Based on the motion picture A Christmas Story distributed by Warner Bros., written by Jean Shepherd, Leigh Brown and Bob Clark, and upon In God We Trust: All Others Pay Cash written by Jean Shepherd. Produced with permission of Warner Bros. Theatre Ventures and Dalfie Entertainment. You’ll shoot your eye out! A Christmas Stor…
Event details