Things to Do This Weekend in Charleston

Live Under The Oaks returns this fall with free outdoor concerts every Thursday at 6pm. Hosted by Johnny O’ of 95SX, the series features live music, food trucks, and beer and wine for purchase—perfect for an evening under the stars.

Set sail for a lively night on the Charleston Princess with an unforgettable BBQ & live music cruise. With a fully stocked bar and plenty of open-air fun, it’s the perfect outing for date night, group gatherings, or anyone looking to enjoy Charleston from a new perspective.

This month at Big Gurl, guests can enjoy a relaxed and creative evening with the Watercolor + Pastels workshop—just $12 plus tax, the lowest-priced class of the month. Perfect for newcomers or regulars, the event offers an easygoing way to explore color, unwind, and create something beautiful. All supplies are included, making it an ideal night out with friends or a solo creative escape.

Fridays and Saturdays in October, Bulldog Tours invites guests to explore Charleston’s haunted side with the Spirited Ghost Tour. This guided evening walk through the historic district combines ghostly tales with seasonal cocktails, featuring stops at iconic spots like The Bar at the Spectator Hotel — a 1920s-inspired “spookeasy” perfect for the occasion.

Firefly Distillery’s Fall Food Truck Feastival returns on Saturday, November 1 from 12–4 PM, celebrating the season with more than 20 local food trucks, craft cocktails, live music, and a vibrant vendor market. With free entry and plenty of space to relax by the creek, it’s the perfect fall afternoon for food lovers, families, and friends alike.

Johns Island County Park welcomes guests for a day of bluegrass, barbecue, and family fun. Enjoy live local bands, pumpkin decorating, hayrides, kids’ crafts, and a lively crafters market perfect for early holiday shopping. With classic Southern fare and festive activities for all ages, it’s a fall celebration not to be missed.

Join Deep Water Vineyard for their Weekend Wine-Downs every Saturday, rain or shine! Enjoy $15 wine tastings (hourly, includes a souvenir glass), sip fun drinks from thier patio bar, and relax with live music and rotating food trucks. Bring the whole crew: kids are welcome, and well-behaved, leashed dogs can roam the grounds with you.

Founded in 1989, the Charleston Farmers Market in Marion Square is a beloved community event. You will find a variety of local produce, plants, herbs, and cut flowers as well as breakfast and lunch vendors, live entertainment, and an assortment of juried arts and crafts from local artisans every Saturday at the Market.

The Sunday Brunch Farmers Market takes place year-round behind The Charleston Pour House, featuring 40+ local vendors, live music, delicious food, and a full bar. Open Sundays from 11am–3pm, with free live music on the deck stage until 9.