Downtown Ocala is glowing this week — pumpkins, lights, live music, masquerades, and monsters (friendly ones, mostly). Whether you’re chasing chills, laughter, or local brews, there’s something every night leading up to Halloween weekend. Here’s your go-to guide for Monday, October 27 through Sunday, November 2 — straight from the Ocala Main Street Calendar.
👻 Monday, Oct. 27 – Open Mic Comedy at Mutiny
9–11 PM | 46 S Magnolia Ave
Ease into the week with something wickedly funny. Mutiny’s open-mic nights serve up gut-busting jokes, good drinks, and downtown’s best people-watching. Sign-ups at 8:30 — no cover, all courage required.
💀 Wednesday, Oct. 29 – Drop the Mic! & Ladies Night
Drop The Mic! | 7:30 pm | 520 NE 1st Ave | Muddy Lotus
Get ready for a high-energy performance-open mic night where voices, beats and boldness take center stage. This event invites local artists, vocalists and spoken-word performers to “drop the mic” in downtown Ocala’s creative heartbeat — come early to audition, bring your courage, and leave the norm at home. 👉 Event link
LADIES NIGHT – Vibes by Dizzlephunk | 8:00 PM | 44 S Magnolia Ave | Mutiny
A women-forward evening of drink specials, live music and big energy hosted by Dizzlephunk.Expect specialty drink deals for the ladies starting at 8 pm, with music kicking off at 9 pm — Mutiny transforms into the go-to Wednesday night destination for bold laughs, dancing and fresh vibes this Halloween week.👉 Event link
🕸️ Thursday, Oct. 30 – Ghouls for Good: Dreamscapes & Nightmares
6:30–9:30 PM | Marion Cultural Alliance, 23 SW Broadway St
It’s a masquerade of mayhem! Join MCA for an eerie-elegant evening of twisted fairytales, crafted cocktails, and hauntingly beautiful art. Costumes encouraged; proceeds support local artists. 👉 Event link
👻 JB Golf Carts 2nd Annual Customer Appreciation Movie Night
7:30 PM | The Marion Theatre, 50 S Magnolia Ave.
A relaxed outdoor/indoor movie-night thanks to JB Golf Carts showing gratitude to customers with a special screening at the historic Marion. Join fellow supporters, swing by early for snacks and mingle under the marquee. 👉 Event link
🎃 Friday, Oct. 31 – Critter Meet & Greet at the Discovery Center
3–4 PM | 701 NE Sanchez Ave
Before the candy chaos begins, stop by the Discovery Center for a not-so-spooky animal encounter! Perfect for families who love science and nature — and maybe a few creepy-crawlies. 👉 Event link
Shrek Halloween Party at The Lodge | 6:00 PM | The Lodge Ocala
An unconventional twist on Halloween: come costume-clad to celebrate in swamp-style at The Lodge with “Shrek” themed fun. Expect ogre-sized laughs, photo-ops, themed décor and maybe a “bog-lit” drink or two as The Lodge transforms into a fairytale-turned-freakshow just in time for the spooky weekend.
Halloween Party at Midtown Station | 7:00 PM | 235 NE Watula Ave
Downtown’s Midtown Station throws open its doors for a big-energy Halloween party with costumes, dancing and late-night fun. This is where the adult crowd heads for full-on Halloween mode: DJ sets, themed cocktails, costume contests and a festive soundtrack that keeps the night going into Sunday.
Black Sheep Halloween Party | 7:00 PM | 128 SW Broadway St
A moody, stylish Halloween party at Black Sheep featuring music, cocktails and a darker edge to your Saturday night. Plan for a 21+ vibe, edgy costumes encouraged, and a venue that delivers a little alternative flavor to the usual downtown haunt hike — this is the after-hour chapter of your holiday weekend.
The Rocky Horror Picture Show | 8:00 PM | The Marion Theatre
Join the cult classic screening of “The Rocky Horror Picture Show,” complete with props, audience participation and full Halloween flair. Expect a crowd in costume, singing along, shouting lines back and fully embracing the eccentric and wild spirit of Rocky Horror — perfect for Friday or Saturday night if you want to dive head-first into the spookiest of spirits.
🕯️ Saturday, Nov. 1 – Día de los Muertos Market | 7:00 PM | 403 SE Osceola Ave
A colorful, culturally rich market celebrating the Mexican holiday of Día de los Muertos with vendors, art, food and traditions. A daytime change-of-pace from the night parties: stroll through booths, pick up artisan goods, experience live music & altars, and soak in the rich heritage of remembrance as the holiday week winds down.
Dentallica Perform Metallica Classics | 7:00 PM | O’Malley’s 24 S Magnolia Ave
Get loud: a local cover band delivers faithful and fiery renditions of Metallica’s greatest hits — perfect for the head-bangin’ Halloween crowd. If you’re ready to rip off the costume mask and rock out, this one’s for you: full volume, full energy, and the kind of live music that keeps your heart racing past midnight.
Fall Festival at the Ocala Downtown Market | 12:00 PM | 403 SE Osceola Ave
A family-friendly festival featuring autumn crafts, food trucks, live music and pumpkins at the downtown market. A great Sunday or daytime wrap-up to the week: bring the kids, enjoy seasonal treats, pick up local artisan goods, and soak in the final moments of Halloween-week in a more relaxed, daylight setting..
🧙♀️ Downtown Halloween Tips
- Costumes encouraged at nearly every event!
- Parking: Use the Downtown Ocala Map for garages and lots.
- Follow: Tag your pics with IG: @ocala_main_street FB: @ocalamainstreet