What’s Happening on HHI This Fall? Festivals, Parades, and Holiday Weekends Worth Planning Around

October through December is one of the best times to visit Hilton Head Island. With comfortable beach weather lasting well past November, smaller crowds than the summer rush, and a lineup of signature cultural and holiday events, the fall and early winter seasons make for an ideal getaway. Here is a look at what is coming up on the island:

Now Through November 22: Crescendo, An Annual Celebration of Art and Culture

Crescendo is the island’s annual arts and culture celebration, presented by the Office of Cultural Affairs and the Arts Council of Hilton Head. It runs through November 22 and serves as the umbrella for much of what is happening culturally on the island this fall, including live theater, poetry readings, exhibitions, and musical performances. This is an engaging and exciting event to keep in mind as you plan your Hilton Head itinerary.

October 28 and November 4: Poetry and Patrón at Tio’s Latin American Kitchen

Poetry and Patrónd runs Wednesday evenings at Tio’s Latin American Kitchen in Shelter Cove Towne Center, with seating from 5 pm and poetry starting at 6 pm. October 28 features poet Dan Hawkins and an open mic night from Island Writers’ Network. November 4 features poet Kathleen Nailey. If you want an evening that feels genuinely local rather than touristy, this is it!

October 30: Motorcars and Music with Taylor Hicks and Folderol

If you are coming for the Concours d’Elegance weekend, arrive Thursday evening to enjoy  Motorcars and Music at Port Royal Golf Club! October 30 kicks off the weekend with Taylor Hicks, the American Idol-winning singer whose blend of soul, blues, and Southern rock translates exceptionally well to a live outdoor setting, followed by local favorite Folderol. It is a proper evening under the Lowcountry sky and a great introduction to Concours weekend!

October 31 and November 1: Concours d’Elegance

The  Hilton Head Island Concours d’Elegance at Port Royal Golf Club runs both days from 9 am to 4 pm. Rare vintage automobiles, modern performance vehicles, and enough variety that you do not need to be a car enthusiast to spend a few hours there and find it an amazing experience. General admission tickets are available at the door and in advance at hhiconcours.com.

November 7: Hilton Head Island Oyster Festival

The  Hilton Head Island Oyster Festival at Lowcountry Celebration Park runs from 11 am to 5 pm on November 7. Local oyster clusters, shrimp, live music, and an outdoor setup that has made this a reliable island tradition for years. Tickets are required at hiltonheadoysterfestival.com. Parking near the park fills up early, so plan to arrive by 10:30 am or park near Shelter Cove and walk over.

November 14: Hilton Head Island Lantern Parade

The  Hilton Head Island Lantern Parade is an amazing event worth building a weekend around!

It steps off at sunset, around 5:45pm, from Alder Lane Beach Access and follows the shoreline to Coligny Beach Park. The full event runs from 5:30 to 8:30 pm. Created by artist Chantelle Rytter, it is a free community parade that moves along the beach entirely by lantern light. Hundreds of people participate every year, and the effect on the beach after dark is something that photographs cannot fully capture. The only requirement to join is bringing a lantern.

Park at Coligny Beach before 5pm and walk north to the Alder Lane start. The streets around the parade route fill up fast once the sun starts going down.

November 26: Two Turkey Trots!

If you enjoy a running experience or two during vacation, Hilton head brings exactly that on Thanksgiving morning! The  38th Annual Turkey Trot 5K and Fun Walk starts at 8am at Dockside on Skull Creek and includes a one-mile fun walk. Bring a nonperishable food item for the Deep Well Project food drive. The  Palmetto Dunes Turtle Trot 5K starts at 9am at the Dunes House and runs along the beach, which makes it the more scenic of the two trots. 

November 27: Gregg Russell Thanksgiving Concert

The  Gregg Russell Thanksgiving Concert will be under the Liberty Oak in Harbour Town, Sea Pines, from 7:30 to 9pm. Free, no tickets needed. The concert closes with the lighting of the Harbour Town Christmas Tree. Bring a blanket and arrive by 7pm for a good spot under the oak!

^{Photo by Seapines.com}

December 4: Winter Wonderland Festival

The  Winter Wonderland Festival at Shelter Cove Park runs from 4 to 7 pm. Free admission, bounce houses, a holiday parade, a DJ, and a Golden Candy Cane Hunt at 5:30 pm. Food and some activities cost extra. A good option if you are on the island for an early December stay with kids!

Booking Your Stay

The Vacation Company has been managing Hilton Head vacation rentals since 1988. We know these neighborhoods and these properties well and are happy to help you find the right fit for your group and your dates.

A few current specials worth knowing about before you book:

Winter Savings at 8 Rum Row! Save 25% for stays between January and March 2027 with promo code WINTERATRUMROW. Settle in, slow down, and enjoy island living with plenty of time for beach walks, golf, dining, and relaxation in the comfort of your home away from home. 

Save 10% on four or more nights at select  oceanfront properties through January 30 with promo code WINTERGETAWAY10. 

The  17 Mallard Holiday Getaway promotion runs November through early January with promo code 17MALLARDHOLIDAY and includes complimentary spa heat in November.

Browse all current offers at  vacationcompany.com/specials or call us at 843.686.6100.