Fall is one of Hilton Head’s most festive times of year.
When the summer crowds thin out, the Island shifts into a relaxed, local vibe—perfect for enjoying food, art and music outdoors in the cooler coastal air.
Listen to a little background from our very own, Erika Hayes, on Dave & Dale at EXP Realty‘s Real Talk podcast about Hilton Head’s Fall Festival Season:
Here are a few highlights of festival season on Hilton Head:
Harbour Town Fall Fest:
Enjoy the splendor of Harbour Town and some great deals at the Harbour Town Fall Fest on Sept. 14 from 11 a.m.-6 p.m. Festivities include: a sidewalk sale, live music with Deas-Guyz, nautical activities, the Carolina Dreamers Car Club, dining and children’s activities. www.seapines.com/experiences/events/harbour-town-fall-fest.
Hilton Head Island Jam:
Join the fun Sept.18-21 for the 3rd Annual Hilton Head Island Jam — a one-of-a-kind songwriters festival. Enjoy a phenomenal group of hitmakers, storytellers, and rising stars for an unforgettable weekend of live music as some of Nashville’s top hitmakers and incredible local talent perform at the Island’s premier venues. www.hiltonheadislandjam.com.
The Hilton Head Island Shrimp Festival:
The Sea Pines Resort hosts the Hilton Head Island Shrimp Festival on Sept. 20 from 1-4 p.m. The family-friendly event will feature savory shrimp dishes prepared by 15 area chefs, craft beers, specialty vendors and performances by Nashville songwriters: as part of the Hilton Head Island Jam Songwriters Festival. An activity-filled “Kid Zone” with a bounce house, face painting, crafts and more. www.seapines.com/shrimp-festival.
3rd Annual Rhythm & Brews Festival:
Head over to the Shelter Cove Community Park on Saturday, Sept. 27 for Rhythm & Brews! Enjoy a live show by headliner Kaylee Rose and 100+ unlimited beer, spirit and wine tastings. Our 3rd annual event, presented by Hilton Head Island Wine and Food Festival, supports ALES for ALS. Every ticket purchased supports their important research. They will be pouring from national and local breweries all afternoon long. The performing headliner will be Kaylee Rose from 3:30-5 p.m. Kaylee Rose is a bold Nashville-based singer-songwriter with a unique musical style. She brings her high-energy brand of music to every performance, from full-band shows like CMA Fest to acoustic gigs like the Bluebird Cafe. The opening Act takes the stage from 2-3:30 p.m. www.hiltonheadrhythmandbrews.com
The 15th Annual Italian Heritage Festival:
The Hilton Head Italian Heritage Festival will be held Saturday, Oct. 18, 11 am – 4 pm, at The Coastal Discovery Museum at Honey Horn – rain or shine. The Festival is a robust celebration of Italian culture with food and live entertainment. The crowd-pleasing grape stomping contest will return as will the pizza eating contest and a full slate of activities for locals, visitors, and kids. Booths will be dedicated to traditional Italian foods – many sponsored by local restaurants. A silent auction will feature an extensive selection of gift certificates to golf foursomes at our world-famous courses, area restaurants, boat cruises, spa visits, and of course, gift baskets, and a wide range of gifts and artworks on which to bid. www.iachh.org/italian-heritage-festival.
Lowcountry at the Fish & Grits Music Festival:
Celebrate the sights, sounds, and flavors of the Lowcountry at the Fish & Grits Music Festival on Oct. 4. from 12–6 p.m. The Lowcountry Celebration Park will transform into a lively celebration of Gullah Geechee culture, live music, mouthwatering seafood, and talented local artisans. www.fishandgritsmusicfest.com.
Rock N Ribs 2025
On Oct. 25 from 5-10 p.m. at Coligny Plaza, enjoy an amazing night of music and barbecue for a good cause with Rock N Ribs 2025! This year features a ONE NIGHT ONLY event with music by Algorhythm, Cranford Hollow, and a late-night set by Nick Poulin. Plus, ALL-YOU-CAN-EAT BBQ (5:30-7:30 p.m.) from local and regional superstar pitmasters, Orchid Paulmeier (One Hot Mama’s & Food Network), Judd Foster (Hootenany BBQ), Slowcountry BBQ, Local Pie, and More!
Hilton Head Island Concours d’Elegance & Motoring Festival:
From Oct. 29-Nov. 2, the Hilton Head Island Concours d’Elegance & Motoring Festival invites you to explore a tapestry of iconic vehicles and cutting-edge innovation, all against the stunning backdrop of Hilton Head Island. It’s a world-class event showcasing rare and classic cars, complete with elegant gatherings and aviation displays. www.hhiconcours.com.
Hilton Head Oyster Festival:
On Nov. 7 and 8, don’t miss one of Hilton Head Island’s biggest events, Oyster Festival! An Island tradition for over 30 years and is beloved by locals and tourists. Oyster Festival features our local oyster clusters and shrimp. This Island Rec family fun event has live music, great atmosphere, and delicious food. A Lowcountry favorite, celebrating oysters roasted, stewed, and steamed—plus live music, craft beer, and family activities. www.hiltonheadoysterfestival.com.
