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.