May Events in the Lowcountry: Food, Fun, Music & More!
The Lowcountry is buzzing with energy this May, with a calendar packed full of vibrant events perfect for locals and visitors alike. From culinary celebrations and Derby Day festivities to outdoor concerts and family-friendly festivals, there's something for everyone to enjoy. Here’s your go-to guide for what’s happening this month across Bluffton, Hilton Head Island, Beaufort, and Port Royal.
Taste of Beaufort
May 2–3, 2025 | Henry C. Chambers Waterfront Park
Celebrate the culture, cuisine, and music of the Lowcountry at the beloved Taste of Beaufort festival. This foodie’s paradise brings together some of the best local dishes in a scenic waterfront setting. Come hungry—you won’t leave disappointed!
Kentucky Derby Celebrations – May 3, 2025
Pull out your best hats and get ready for the most exciting two minutes in sports at these festive Derby Day parties:
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Calhoun Street Tavern, Bluffton
Enjoy live music by Muddy Creek Band (6–9 PM), mint juleps, and premium bourbon at Bluffton’s top whiskey bar. Come early and celebrate in style! -
Dockside Restaurant, Bluffton
Join the fun at the Shark Bar with Derby fare, mint juleps, and a Best Derby Hat Contest judged by popular vote at 5 PM. -
Burnt Church Distillery, Bluffton
Watch the race from the distillery, Hail Mary's, or Square 67. Mint juleps are just $15, and the first 48 get a collectible glass! -
The Bank, Hilton Head Island
Enjoy mint juleps all day long as you watch the race with friends and neighbors. -
Nectar Bluffton, Old Town Bluffton
Catch the Derby on 9 TVs, sip $6 Vinho Verde, enjoy live music by Ben Hughey, and compete to win a $100 gift card for best Derby attire!
Beaufort Water Festival 5K/10K Run
May 3, 2025 | 8:00 AM | Live Oak Park, Port Royal
Get your heart pumping at the 69th Annual Beaufort Water Festival's scenic 5K/10K. Runners will enjoy moss-draped oaks and waterway views.
Family Fun Day
May 3, 2025 | 12:00–3:00 PM | Island Rec Center, Hilton Head
A completely free day of fun with bounce houses, snow cones, popcorn, rock climbing, games, and more—perfect for the whole family!
Port Royal Street Music
May 3, 2025 | Port Royal
Soak up live music in one of the Lowcountry’s most charming towns.
Pedal Hilton Head Island
May 4, 2025 | 7:30 AM–12:00 PM | Lowcountry Celebration Park
Support local youth at this annual cycling fundraiser hosted by the Boys & Girls Club. Choose your route and ride for a great cause.
Music & Taste on the Harbour
Every Thursday | Shelter Cove Harbour
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May 1: Target feat. Headliner Horns
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May 8: Deas Guyz
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May 15: The Nice Guys
Enjoy local music, tasty bites, and drinks under the stars. Admission is free—just bring a canned good for the Deep Well Project!
MayFest 2025
May 10, 2025 | 10:00 AM–5:00 PM | Old Town Bluffton
A Bluffton tradition! Over 160 artists, 30+ food trucks, two stages of live music, and plenty of local flair. Bring a chair, wear sunscreen, and make it a day to remember.
The Sound of Taste: A Musical Culinary Experience
May 10, 2025 | 5:30–7:30 PM | The Westin Hilton Head Island
A unique event combining flavor and rhythm. Enjoy curated dishes paired with music to delight all your senses, led by musical culinarian Teaker Harris, Jr.
Big Band Concert
May 16, 2025 | Hilton Head Beach & Tennis Resort
Dance the night away with the Hilton Head Big Band. Doors open at 5:30 PM, with music starting at 6:00 PM. Food and drinks available on-site.
Bluffton Sunset Party: Sunsplash Palooza
May 16, 2025 | May River, Bluffton
An evening of live music, local food and drinks, and riverside vibes. The perfect Friday night wind-down with the community.
Cornhole for a Cause: Support Local Veterans
May 17, 2025 | 12:00–6:00 PM | 17 Market, Beaufort
Toss bags and raise funds to honor veterans. Fun, competition, and giving back all in one afternoon.
Hilton Head Island Art Festival
May 23–25, 2025 | Shelter Cove Harbour
Shop stunning U.S.-made artwork over Memorial Day weekend. Enjoy three days of shopping, dining, and entertainment by the marina.
Hilton Head Choral Society's "America Sings!" Concert
May 25, 2025 | 7:00–8:30 PM | First Presbyterian Church
End the month with a patriotic celebration of music honoring those who serve. Featuring the Hilton Head Choral Society and Category V Brass.
Whether you're looking for live music, food and drink festivals, family fun, or ways to give back, May in the Lowcountry has it all. Mark your calendars and make the most of this vibrant season!
