Angel's Envy Bourbon Dinner- October 3rd
The return of our Bourbon Dinner season! This year, kicking things off with an unforgettable evening featuring the renowned Angel’s Envy bourbon. Mark your calendars for Friday, October 3, and join us at the Sea Pines Beach Club for a night of exquisite bourbon tastings paired with a delectable multi-course dinner.
Italian Heritage Festival - October 18th
Mark your calendars for a delightful day of Italian culture and celebration at the Hilton Head Italian Heritage Festival! Join us on Saturday, October 18, 2025, from 11:00 am to 4:00 pm at the scenic Coastal Discovery Museum at Honey Horn. Whether you’re a local or visiting, there’s something for everyone at this vibrant event – happening rain or shine!
Halloween on the Harbour- October 26th
On October 26th, the community will transform into a vibrant tapestry of costumes and laughter, offering a perfect blend of activities, games, and trick-or-treating. The highlight of the day? A Halloween fashion show on the famous Liberty Oak stage at 2:30 PM. This is your chance to showcase your creative costumes and join in the festive spirit. All ages are welcome, and costumes are encouraged, so bring your imagination and enjoy a day of spooky fun!
Hilton Head Island Motoring Festival & Concours d'Elegance - October 29th thru November 2nd
Nestled in the heart of the picturesque Lowcountry, the Hilton Head Island Concours d’Elegance & Motoring Festival is a celebration of automotive excellence and luxury that you won’t want to miss. This annual event, held on the stunning Hilton Head Island, showcases an exquisite collection of rare automobiles and vintage motorcycles, offering enthusiasts and casual visitors alike a unique glimpse into the world of classic motoring.
Hilton Head Island Multihull Regatta-October 29th thru November 2nd
Join us on Friday, Saturday, and Sunday for a weekend packed with both distance and buoy racing. The race schedule, meticulously crafted by our dedicated committee, will vary to ensure optimal conditions and maximum enjoyment. Participants will experience the challenge and exhilaration of competing in the open waters off Hilton Head Island Beach.
Hilton Head Oyster Festival- November 7th and 8th
Mark your calendars for one of Hilton Head Island’s most anticipated events! On November 7th and 8th, 2025, the Oyster Festival promises an unforgettable experience filled with mouthwatering seafood, lively music, and an atmosphere buzzing with excitement. Whether you’re a local or a visitor, this event is a cherished tradition that has been delighting attendees for over 30 years.
Osprey Village Golf Tournament- November 9th
Join us for an unforgettable day of fun, camaraderie, and friendly competition at the 7th Annual Osprey Village Golf Tournament! This year, we’re excited to welcome participants to the scenic Golden Bear Golf Club in Indigo Run on Hilton Head Island, happening on Sunday, November 9th. Whether you’re a seasoned golfer or just enjoy the game, this event promises to be a delightful experience for everyone involved.