Rose’, Rosas, and Roses 2026 | WDDT

Downtown Brandon

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.

Back to School Ducks in a Row 2026 | WDDT

Downtown Brandon

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.

Go Pink – Witches’ Night Out 2026 | WDDT

Downtown Brandon

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.

Friendsgiving 2026 | WDDT

Downtown Brandon

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.