May 2025 Events on Hilton Head Island

Hilton Head Island is a fantastic getaway year-round but visiting in May offers a unique blend of pleasant weather, fewer crowds, and some great activities. If you are looking to visit this May, here what you can expect for events. There are a few fun things going on to check out! 

Pedal Hilton Head Island

Sunday, May 4, 2025

Pedal Hilton Head Island is a premiere cycling fundraiser for the Boys & Girls Club of Hilton Head Island and now in its 19thyear. There are 5 cycling route options from which to choose – designed from beginner to advanced so there is something for everyone. For the avid cyclist, choose a 62-mile, metric century ride (available in 2 paces) or 40-mile ride.  Cyclists love riding on Hilton Head Island because it’s relatively flat compared to Greenville or Asheville!  Pedal also hosts 30-miles, 20-miles, and 2-miles. The ride concludes with a festive party with live music and lunch included with your registration fee. Registration also includes a t-shirt and starts at $85 per ride. Ride times are staged beginning at 7:30 am from Lowcountry Celebration Park, 90 Pope Avenue, Hilton Head Island, SC.  The event raises over $100,000 for the Boys & Girls Club of Hilton Head Island which serves children in our area who need it most. Beachside Getaway is proud to sponsor this event for the third year in a row!!! 

Visit www.pedalhhi.org to register to ride. 

Hilton Head Island Arts Festival 

At Shelter Cove Harbour & Marina 

May 23 - May 25th, 2025 

Join us for a weekend of art, shopping, dining, and entertainment! The Hilton Head Art Festival will feature the work of artists in various mediums; pottery, glass, wood, jewelry, metal, painting, photography and much more. The festival will take place along the harbour and marina promenade, inviting visitors to browse our talented artisans and shop and dine along the marina. Enjoy live local entertainment each day. Admission is free!

Hilton Head Island Farmer’s Market 

Tuesday’s – 9 am – 1 pm 

The Hilton Head Farmers Market gathers every Tuesday from 9 a.m.-1 p.m. at the Costal Discovery Museum’s Honey Horn campus. Visit with our expanding list of regular vendors, plus a rotating schedule of food trucks and new arrivals. The HHI Farmers Market roster includes area growers providing the freshest local produce, pasture-raised chicken, fresh eggs, free-range rabbit, pork, hand-made sausage, fresh baked goods from cookies to breads, and of course the best of our area’s seafood, She Crab Soup and more. A great outing for the whole family and a great way to support our community’s vendors and small businesses while taking quality goods home to our familiesShop local, meet new friends, strengthen our community, and rebuild our local, sustainable food economy!

Aside from these great events, May marks the transition from spring to summer, usually bringing mild temperatures and lower humidity. Average highs hover around the mid-80s F, making it perfect for outdoor activities. The comfortable weather allows you to enjoy everything from beach lounging to walking, without the sweltering heat that often comes in the peak summer months.  You will also find that as one of the first months of the tourist season, May is less crowded than the peak summer months of June through August. This means you can enjoy the island's beautiful beaches, restaurants, and attractions without as many crowds!