Guide to May Events

a large brick building with trees in front of it

Event season is heating up in Charleston! May has many events to choose from, including festivals, concerts, and wine strolls! Take a look at a list of a few of our favorite May events in Charleston!

Live Under the Oaks

When: Every Thursday in May at 6 pm

Where: Mount Pleasant Towne Centre - 1218 Belk Dr

Head on over to Mount Pleasant and enjoy some free live music every Thursday in May! Each week a different artist will perform at the Mount Pleasant Towne Centre along with a featured food truck. Check out their website for a full list of performers and food trucks! 

Garden Stroll and Wine Tastings at Middleton Place

When: May 3, 2023 & May 10, 2023

Where: Middleton Place - 4300 Ashley River Rd

Grab a refreshing glass of wine and spend the evening exploring America's Oldest Landscaped Gardens! Taking place from 5:30 pm to 7:30 pm, participants will get to enjoy this Historic Landmark's beautiful greenery and take in spectacular views of the Ashley River. Tickets for this event are $35. 

40th Annual North Charleston Arts Festival

When: May 3-7, 2023

Where: Various locations

Enjoy an assortment of local and regional artists at the 40th Annual North Charleston Arts Festival! From different performances to an array of exhibitions and activities, there is something for everyone to appreciate! Check out the event's website for a full calendar of events going on throughout the week. Please note that some events require pre-registration; however, admission and parking for each event are free. 

Music in the Park

When: May 6, 2023

Where: Isle of Palms Recreation Center

Looking to enjoy some good music and good food? If so, look no further than Music in the Park in Isle of Palms! Kick off the afternoon with The Blue Plantation Band at 3 pm, followed by The Bluestone Ramblers at 5 pm. Holy City Popcorn, Empanada Cruisines, and Mora Iced Creamery will be serving food during the performances! Admission to this event is free. 

Annual Charleston Greek Festival

When: May 12-14, 2023

Where: Greek Orthodox Church of the Holy Trinity - 30 Race Street

Immerse yourself in Greek culture at the Annual Charleston Greek Festival! Dating all the way back to 1970, this is the 3rd largest event in the Lowcountry. This highly anticipated event is complete with delicious Greek food, wine, and, best of all, live music and dancing! Tickets for this event start at $5, and children under 12 get in free. 

Sip & Stroll at Drayton Hall

When: May 13, 2023

Where: Drayton Hall - 3380 Ashley River Road 

Grab a glass of wine or a local brew and enjoy one of Charleston’s most spectacular outdoor events. Those taking part will get to enjoy a drink of their choosing while listening to Drayton Hall’s new Landscape Audio Tour. To end the tour, guests will receive a complimentary wine glass or koozie to keep for themselves! Tickets for this event start at $35 for members and $40 for nonmembers. 

Summer Samba

When: May 13, 2023

Where: Charleston Music Hall - 37 John Street 

Immerse yourself in the vibrant world of Brazilian jazz right in the heart of downtown Charleston! Taking place on May 13th, there will be two sets, one starting at 5 pm and the other at 8 pm. Tickets for this event start at $10. 

Chucktown Comedy Week

When: May 17 - 21, 2023

Where: Various Locations

Looking for a good laugh? If so, check out Chucktown Comedy Week! With comedians coming in from across the country, this event is sure to keep you laughing all week long! Tickets are on sale now based on what event you would like to attend. 

May events in Charleston are not the only reason to visit--history, charm, food, and beaches are just a few more reasons to make Charleston your next vacation or staycation!

Wine on the Piazza

When: May 18, 2023, 4:30 pm-6:00 pm

Where: Edmondston Alston House - 21 E Battery

Looking for the perfect Charleston evening? If so, look no further than Wine on the Piazza at the Edmondston Alston House! Those taking part will get to enjoy a glass of wine, spectacular views of the Charleston harbor, and a self-guided tour of this historic Charleston home. Tickets for this relaxing evening start at $30 per person. 

Kenny Chesney Concert

When: Thursday, May 25, 2023

Where: Credit One Stadium - 7596, 161 Seven Farms Drive

Check out Kenny Chesney at Credit One Stadium! For one night only, see Kenny Chesney at his I Go Back Tour along with his special guest, Kelsea Ballerini! Tickets for this event start at $120. 

Spoleto Festival USA

When: May 26-June 11, 2023

Where: Various locations

Spoleto Festival USA is one of America's major performing arts festivals. It was founded in 1977 by Pulitzer Prize-winning composer Gian Carlo Menotti, who sought to establish a counterpart to the Festival Dei Due Mondi in Spoleto, Italy. The 17-day event transforms Charleston into an exhilarating celebration of performing, literary and visual arts.

Charleston Farmers’ Market

When: Saturdays, April 8-November 25, 2023

Where: Marion Square-329 Meeting Street

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.

RiverDogs Minor League Baseball

When: Games throughout May

Where: Joseph P. Riley, Jr. Park

Get the family together, head on over to Joseph P. Riley, Jr. Park, and enjoy Charleston’s very own Minor League Baseball team! From waterfront stadium views to an array of food and drink vendors, a Charleston RiverDogs game makes for the perfect summer night. Also, make sure to check out their promotions page to see what special-themed nights they have going on this month. Tickets for the 2023 season are on sale now!