This Weekend on Hilton Head

Looking for some local fun on the island this weekend? We’ve got all the information you’ll need to have a fun-filled weekend with family and friends.


Placing bets and taking names? Checkout some of the island’s hottest Derby parties while enjoying some of Kentucky’s finest racing traditions right here in the Lowcountry.

Derby Day at Captain Woody’s – Today 5/2 4:00pm
Race time begins at 6:00pm with plenty of mint juleps and Kentucky’s finest beer cheese followed by live music and trendy contests to show off your best Derby hats and preppy pants.

Salty Dog’s Derby Party – Today 5/2 4:00pm – 7:00pm
Wear your hats and bring an appetite because this party has it all! With multiple big screens, you’re sure to have the greatest views so you can place the best bets! To top it off there will be plenty of cookout favorites along with mint juleps, hot browns, and bourbon specials so you can party just as if you were at the Derby!

Heroes on Horseback – Today 5/2 4:00pm
Join the elite at Moss Creek Clubhouse for one of the largest local fundraising events of the year. Enjoy an afternoon of live and silent auctions, Derby hat contests, bourbon tasting, and plenty of tapas with beer and wine to keep you going throughout the evening.


What to do before and after the races?

Beer, Bacon & Music Festival – Today til 5:00pm
Come on out to Shelter Cove Community Park to enjoy a themed block party with the full-scale festival experience. Enjoy tasty treats from local restaurants, life entertainment from some of the island’s best bands, and friendly competitions put on by the island Rec Center.


Hilton Head Island Boat Show – Today through Sunday 6:00pm
Get a taste of the island life…on the water! Join your family and friends out at Windmill Harbour for a full weekend of fun! Shop local vendors while enjoying demonstrations and live entertainment from some of the island’s most popular businesses. If you’re looking to get out on the water, this is the perfect place, with paddleboard and kayak demos all weekend while you look at some of the coolest boats in the Lowcountry.

Relay for Life – Today til 12:00am
Bring your family to Hilton Head High School and support those battling cancer by taking part in various activities such as the Survivor’s Walk and Luminaria Ceremony. There will even be a Survivor’s Dinner at 5:30pm and silent auctions with games and food along with plenty of entertainment for all ages.


11th Annual Yacht Hop – Sunday 5/3
Come sail away (or at least pretend to) at the Harbour Town Yacht Basin while enjoying wine and hors d’oeuvres by some of the island’s top chefs. Enjoy live entertainment and auctions as you hop from yacht to yacht, living the good life! Proceeds of this event benefit patient care programs at Hospice of the Lowcountry.


Chamber Bike & Dine Week – Today through Saturday 5/9
Sometimes you have to work a little harder for your food! Bike to your favorite dining spots around the island, with special menus and discounts for cyclists during the week. Enjoy special breakfast, lunch, or dinner offers from some of your favorite local restaurants. Visitors and residents are welcome, as long as you are on a bicycle!