May on Hilton Head Island is pure magic – warm sun, cool ocean breezes, and a calendar packed with can’t-miss events. Here’s what you need to know about upcoming May Hilton Head events when you’re making vacation plans.
Pedal Hilton Head Island – May 4
Kick off the month with the island’s biggest cycling event. Pedal Hilton Head Island offers routes from 2 to 62 miles so everyone can join – families, and serious cyclists alike. The ride supports the Boys & Girls Club and wraps up with a party at Lowcountry Celebration Park. Registration starts at $85; last year’s event raised over $100,000 for local kids!
Mayfest – May 10
Head to historic Bluffton for Mayfest, a beloved Lowcountry tradition. Expect 130+ artists, food vendors, live music, and quirky contests like the Ugly Dog Competition and the classic pie-eating showdown. Admission is free, and the fun runs all day.
Music & Taste on the Harbour
Every Thursday in May, Shelter Cove Harbour comes alive with live bands, local eats, and waterfront views. Catch Deas Guyz on May 8 and The Nice Guys on May 15th. Bring your lawn chair, grab a bite, and dance under the stars.
Hilton Head Art Festival – May 23-25
Memorial Day weekend means art, shopping, and entertainment at Shelter Cove Harbour & Marina. Browse work from top artists, enjoy live music, and sample local flavors. The festival runs Friday through Sunday, and admission is free.
Weekly Markets
- Hilton Head Farmers Market: Tuesdays, 9am – 1pm at Coastal Discovery Museum. Stock up on fresh produce, baked goods, and seafood.
- Hilton Head Community Market: Saturdays, 9:30am -12:30pm at Shelter Cove Community Park. Meet local makers and grab a treat.
Perfect Weather for Exploring
May brings highs in the low to mid-80s and fewer crowds than summer. It’s ideal for renting a bike to cruise the island’s 60+ miles of scenic trails, hit the beach, or explore local parks. Make the most of your May on Hilton Head Island. There’s something for everyone – just don’t forget your sunscreen!