Magic of Lights is a drive-through holiday light experience featuring dazzling displays, themed scenes and festive music. Families can enjoy the show from the comfort of their vehicle as they […]
Let It Glow is the City of Brandon’s Christmas lights celebration, where homes and businesses across the community decorate with festive displays. Residents are invited to enjoy an evening drive to see the lights and vote for their favorites.
Join us for one of Brandon’s most anticipated spring events, the Crawfish Crawl 5K, returning to Downtown Brandon on Saturday, April 18, 2026. This family-friendly morning kicks off with a scenic 5K through the downtown commercial and residential district, followed by a lively post-race festival filled with music, food, and fun.
Each stop will feature a 2-oz tasting, with a curated lineup of wines and Brandon-inspired specialty cocktails crafted in partnership with local businesses. Your ticket guarantees access to all featured tastings throughout the evening.
King & Queen of Hearts Poker Run
Join Brandon Main Street on February 7 for the King & Queen of Hearts Poker Run, a free, come-and-go style event that brings a little friendly competition to Downtown Brandon.
From 11:00 AM to 5:00 PM, participants can visit 7 participating downtown retail shops and restaurants, drawing one playing card at each stop. Once you’ve completed your route, turn in your best poker hand at the Brandon Main Street office located at 143 W Government Street anytime between 12:00 PM and 5:00 PM.
There’s no charge to play, making this a fun and easy way to explore downtown, support local businesses, and enjoy the day at your own pace. Whether you’re playing to win or just in it for the stroll, the King & Queen of Hearts Poker Run is a great way to experience Downtown Brandon.
Guests will sip and stroll through participating downtown shops while enjoying 8 curated wine tastings, including 2 wines featured as light, seasonal sangrias. The walkable downtown setting creates the perfect atmosphere to shop, socialize, and enjoy extended store hours in a relaxed, welcoming environment.
This themed tasting event will feature 8 curated wines across 4 downtown locations, with 4 wines served as refreshing mimosa-style pours, perfect for a warm May night and the start of rosé season. Guests are invited to sip and stroll through participating shops while enjoying seasonal décor, extended store hours, and Downtown Brandon’s welcoming atmosphere.
This end-of-summer evening invites guests to relax and recharge with 8 curated wine tastings while sipping, shopping, and strolling through Downtown Brandon. Participating shops will offer extended hours, creating a lighthearted, walkable atmosphere perfect for reconnecting with friends and unwinding before the school year kicks into full gear.
Whether you’re celebrating new routines, a new school year, or simply ready for a well-earned night out, Wine Down Downtown: Back to School – Ducks in a Row is the perfect way to toast the season.
This special Go Pink: Witches’ Night Out edition supports breast cancer awareness while inviting guests to sip, shop, and stroll through Downtown Brandon enjoying 8 curated wine tastings. Festive décor will set the scene, costumes are encouraged, and the atmosphere is upbeat, playful, and adults-only.
The night leads into the ultimate late-night stop at The Gallows for Galloween, an adult Halloween celebration complete with a costume contest to end the evening in spooky style.
For bourbon lovers, a Bourbon Add-On Ticket will be available and includes 4 hand-selected bourbons, adding a bold twist to the night’s tastings.
Grab your witches’ crew, dress in pink with a touch of costume flair, and join us on Main Street for a hauntingly fun night out that celebrates community, awareness, and a great cause.
Join Brandon Main Street on November 19 as Wine Down Downtown returns with a cozy Friendsgiving theme, an evening made for gathering, gratitude, and good company in Downtown Brandon.
Guests will sip, shop, and stroll through participating downtown businesses while enjoying 8 festive tastings, featuring 4 curated wines and 4 warm mulled wine ciders, perfect for cooler November evenings. Extended store hours and a relaxed, fall-inspired atmosphere create the ideal setting to slow down and enjoy the season.
Whether you’re catching up with friends, taking a break from holiday prep, or kicking off the season of gratitude, Wine Down Downtown: Friendsgiving is a welcoming way to raise a glass and celebrate together.
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