When you think of September, you imagine cozy sweaters, crunchy leaves, and all things pumpkin-spiced as the fall season takes over. But if you’re in Hilton Head, the month looks and feels different.
Warm breezes, sunny skies, and ocean temperatures still perfect for a dip? With the summer crowds gone, you’re in for the best getaway!
This September 2025, Hilton Head brings the fun in full force. Check out these events that deserve a spot in your itinerary.
Jazz in the Park
Address: 94 Pope Avenue, Hilton Head Island, SC 29928
Phone: (843) 842-2055
Start the month with smooth vibes and sultry sounds at Lowcountry Celebration Park! Catch Jazz in the Park‘s free open-air concert on September 2nd, featuring none other than the John Brackett Quintet, a local group turned international sensation. Trust the performances to move you.
Harbour Town Fall Fest
Address: 149 Lighthouse Road, Hilton Head Island, SC 29928
Phone: (843) 785-3333
Do you want to stroll through charming shops during a sidewalk sale, savor waterfront dining, and enjoy boat tours and other nautical activities? Make your way to the iconic Harbour Town Fall Fest on September 14th. Go explore the classic car display from the Carolina Dreamers Car Club, too!
Island Jam
Address: N/A
Phone: N/A
From September 18th to 21st, the island becomes a mini-Nashville during the 3rd Annual Hilton Head Island Jam. This songwriter festival introduces some of Nashville’s top hitmakers and stellar local talent! Expect shows across beloved venues like Lowcountry Celebration Park and Liberty Oak.
Hilton Head Shrimp Festival
Address: 149 Lighthouse Road, Hilton Head Island, SC 29928
Phone: (843) 785-3333
Calling all foodies! The 7th Annual Hilton Head Island Shrimp Festival will be on September 20th, hosted by The Sea Pines Resort. This mouthwatering affair serves shrimp creations from over 15 local chefs and craft beer samples from 15 breweries. Get a chance to vote for the coveted “People’s Choice Best Dish” and “Best Brewery” awards!
The Beer Mile
Address: 1014 William Hilton Parkway, Hilton Head Island, SC 29928 (Local Legend)
Phone: (843) 681-7273 (Hilton Head Island Recreation Center)
What about an athletic and hilarious challenge? That’s Beer Mile, happening September 26th. The concept is simple (or not!): Run a mile and drink four beers along the way. Competitors will begin at Bristol Sports Arena, sip their first brew, then take off on a quarter-mile leg. Please don’t forget to get yourself a designated driver!
Celebrate Unity
Address: 540 William Hilton Parkway, Hilton Head Island, SC 29928
Phone: (843) 341-3818
End September 2025 on a powerful and inspiring note with Celebrate Unity, the Hilton Head Choral Society’s kick-off to their 50th season. On September 26th, internationally renowned composer and conductor Z. Randall Stroope will be joining the performing arts organization with a brand-new piece commissioned specifically for the anniversary.
Fall Into Fun With Beachside Hilton Head
That’s a lot of must-attend events. Fortunately, Beachside Hilton Head has vacation rentals ready to send you off in comfort and welcome you back with style. Our properties are thoughtfully designed, immaculately maintained, and always near the buzz.
We’re just as excited as you are about your visit to the island in September 2025. Book your stay now and lock it in! Call Beachside Hilton Head at (843) 983-6620 or contact us online.
