A Seasonal Celebration with Delcher & Delcher
It might seem that the popularity for Hilton Head Island and Bluffton peaks during the summer season. Who doesn’t want to vacation in the Lowcountry?
However, our local area shines especially bright during crisp autumn days and the sparkle of the holiday season. From food and music to art to culture and from annual festivals to holiday traditions, these gatherings bring our community together in unforgettable ways.
We are proud to showcase the fall and winter festivals that make this season so special for residents and visitors alike.
Fall: A Harvest of Community & Culture
1. Harbour Town Fall Fest (Hilton Head Island)
Date: mid-September (e.g., September 14, 2025)
A family-friendly favorite featuring sidewalk sale bargains, live performances by Deas‑Guyz, classic car showcases, boat rides, and waterfront dining in the scenic Harbour Town area.
Why we love it: This lively event offers something for everyone—shop, listen to music, and soak up the Lowcountry ambiance.
2. Hilton Head Island Shrimp Festival
Date: September 20, 2025
A culinary celebration spotlighting shrimp dishes, craft beers, live music, and family-friendly attractions at Harbour Town’s Sea Pines Resort.
Why we love it: A delicious blend of local flavors and festivity, showcasing Hilton Head’s vibrant food scene.
3. Fish & Grits Music Festival (Gullah/Geechee Culture)
Date: October 4, 2025
Join in on the region’s cultural roots with live music, Gullah/Geechee cuisine, arts, crafts, and performances celebrating this deep-seated heritage.
Why we love it: Celebrate cultural history through this one-of-a-kind food and music fusion.
4. Jeep Island Festival
Dates: October 10-11, 2025
Flavor and community spirit set the foundation for the Jeep Island and Chili Cookoff Extravaganza. This vibrant event, set against the stunning backdrop of Hilton Head Island, promises Jeep enthusiasts and food lovers an unforgettable experience.
Why we love it: It’s a fun blend of automotive culture and family fun — perfect for all ages.
5. Historic Bluffton Arts & Seafood Festival
Dates: October 11-19, 2025 (Street Fest: October 18-19)
Fore more than 20 years, Bluffton’s premier fall festival features a street festival, juried art exhibits, seafood tastings, live music, kayak tours, and 5K runs celebrating local culture and coastal cuisine.
Signature flair: A perfect fusion of art and seafood that showcases Bluffton’s creative heritage.
6. Italian Heritage Festival
Date: October 18, 2025
Held at the Coastal Discovery Museum at Honey Horn, this spirited festival sustains Italian-American traditions with grape stomping, pizza‑eating contests, silent auctions, and plenty of pasta, pastries, and live entertainment.
Why we love it: A cultural immersion that’s fun, family-friendly, and delicious.
7. Harbor Elegance: Motoring Festival & Concours d’Elegance
Dates: October 29–November 2, 2025
An elegant showcase of vintage automobiles, aerial displays, and scenic driving tours celebrating classic southern style and automotive history.
Why we love it: A sophisticated event that merges elegance with automotive artistry.
Winter: Festive Cheer Across the Lowcountry
8. Winter Wonderland Festival (Hilton Head)
Date: Early December (e.g., December 6, 2025)
Transform Shelter Cove Park into a holiday wonderland with bounce houses, DJs, food and drink options, and a memorable Golden Candy Cane Hunt.
Why we love it: A cozy, community-centered holiday event that delivers joy and festive spirit to families.
9. Bluffton Christmas Parade
Date: Early December (annual)
Bluffton’s charming holiday procession features festive floats, local bands, and community cheer winding through Old Town.
Why we love it: A heartwarming tradition—ideal for engaging your local audience with seasonal delight.
