May has officially arrived in Charleston, and the calendar is packed in the best way. This is one of those months where you’ll want to say yes to everything—between iconic festivals, live music, and some of our favorite annual traditions, there’s always something happening around town.

One of the most anticipated weekends of the month is the Greek Festival 🇬🇷, where you can expect incredible food (hello, baklava), live music, and a full cultural experience that feels like a mini getaway right here in Charleston. Not long after, Piccolo Spoleto 🎭 takes over the city with performances, art exhibits, and local talent on full display—perfect for anyone who loves Charleston’s creative side. And as we roll further into May, Reggae Nights 🌴🎶 kicks off at James Island County Park, bringing laid-back evenings filled with live music, food vendors, and that classic Lowcountry summer feel.

If you’re looking to mix in a few big events, you’ve got options. Catch Katt Williams for a night of laughs, or grab your friends and head out to see Pitbull bring the energy. And for something uniquely Charleston, the Wadmalaw Wine Mixer is always a standout—great wine, a fun crowd, and the perfect excuse to spend a day supporting local.

Closer to home for us, one of our favorite events of the entire year is back—Dogs, Donuts, & Donations on May 16th 🐶🍩 This event supports Pet Helpers and brings together adoptable dogs, local vendors, raffle and silent auction items, plus coffee and donuts to keep everyone fueled. Whether you’re looking to adopt, support a great cause, or just spend a fun morning with fellow dog lovers, this is one you won’t want to miss. If you’re planning to bring your own pup and enjoy The Broken Leash dog park while you’re there, just be sure to check their website ahead of time for rules and required documentation.

And of course, May wouldn’t be complete without celebrating the real stars of the month—the moms 💐 Mother’s Day is right around the corner, and Charleston always shows up with incredible brunch spots, waterfront dining, and special events to make the day feel extra special. We’ll be sharing a full Mother’s Day guide soon with our favorite places to celebrate and ideas to make the most of the day.

From festivals and concerts to community events and weekend plans, May is one of the best times to experience everything Charleston has to offer. Whether you’re filling your weekends with events or just picking a few favorites, it’s safe to say this month is one to enjoy from start to finish.

Check out the full list of events below! Happy May, Charleston ✨