Kayaking at Dawn

Four Hilton Head Island Weekend Trips You Can’t Miss This Fall

Fall is a fantastic time to visit Hilton Head Island. The weather is still nice and warm, and it’s prime time to enjoy all that the island has to offer: From top-tier auto shows to delicious seafood festivals and a whole lot more! Whatever your travel style, it’s easy to create the ideal fall getaway. Read on to discover four weekend trip itineraries you can’t miss on Hilton Head Island this fall.

For Auto Enthusiasts: Hilton Head Motoring Festival & Concours d’Elegance


old car

When: November 2-4

Where: Around Hilton Head Island

A multi-day motoring festival, the Hilton Head Motoring Festival & Concours d’Elegance is one of the area’s premier events, with many of the most exclusive and exciting shows happening on Hilton Head Island. Classic automobiles, airplanes, and watercraft will be on display and create an atmosphere of timeless elegance. Start on a high note Friday night with cocktails at the Flights & Fancy Aeroport Gala, featuring vintage and new aircraft. On Saturday, walk the 1st and 18th fairways of the Planter’s Row course at the Port Royal Golf Club and admire the best auto entries at the Car Club Showcase, then take a short shuttle over to the Aero Expo.

Complete your weekend with the namesake event, the Concours d’Elegance. French for competition of elegance, this exceptional showcase of classic cars from bygone eras is a must-see for any car buff or lover of the finer things in life. If you can tear yourself away, the ‘Life’ exhibit on vehicles from iconic 24-hours endurance road races promises a unique experience.

For (Sea)Foodies: Bluffton Arts and Seafood Festival



When: October 13 – 21, 2017

Where: Bluffton

Get a true taste of Southern hospitality in charming and eclectic Bluffton. This historic, state-designated cultural district plays host to the annual Historic Bluffton Arts & Seafood festival. Lovers of shellfish and such shouldn't miss this. Arrive early on Friday and take to the water with either a kayak or river boat tour along May River. In the evening, head to the Red Apron Sips and Seafood Party at Hampton Lake for chef demonstrations, Lowcountry dining, and delicious cocktails.

Bring your appetite on Saturday for the Art & Seafood Street Fest in the Historic District on Calhoun Street. Savor local seafood and Lowcountry cuisine served up by area restaurants while you browse the creations of over 100 artists during a juried art show. Stop by DuBois Park for children’s art activities and a fun magic show. Did someone say seafood extravaganza? Hit up Rockin’ on the Dock Saturday evening for oyster roasts, a shrimp boil, BBQ, and a dazzling fireworks grand finale. In case you didn’t get your fill, the Street Fest and Art in the Park continue on Sunday, plus you’ll find a fun Paddle Battle at Bluffton Oyster Factory Park.

For Active Adventurers: 

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There are more awesome outdoor activities to do on Hilton Head Island than you could fit into just one weekend—but if that’s all the time you have, here are some of our favorites. With 33 courses in the area, golf is a definite go-to around here. If you’re getting in on Friday, take a swing at Harbour Town Golf Links and catch a stunning sunset by the iconic lighthouse. With courses by world-renowned architects like Robert Trent Jones Sr., Pete Dye, Davis Love III and Jack Nicklaus, you’ll be spoiled for choice on and around the island.

Hilton Head Island is also home to eight of the world’s top 100 tennis resorts and camps, and these aren’t any old courts. Perfect your serve surrounded by centuries-old oaks, tranquil tidal creeks, and incredible maritime forests. Want to get a little more of the great outdoors on Saturday? Get out on the water with a variety of aquatic activities. Kayak or paddleboard along beautiful waterways and keep an eye out for the island’s diverse wildlife, set out on a fishing expedition, or kick it up a notch with jet skiing, parasailing, surfing and more. Before you depart on Sunday, squeeze in a bike ride along the beach for the quintessential Hilton Head experience and snap some shots that are sure to up your Instagram game.

For Family Fun

walking on the boardwalk

Follow this itinerary. It’s no secret Hilton Head Island is one of the country’s top destinations for fun family getaways. If you’ve only got the weekend to spend, there are lots of awesome activities to make the most of your time on our island. Up for a swashbuckling adventure? Board a pirate ship and set off in search of hidden treasure. Young buccaneers will receive their own pirate name, face paint, temporary tattoos, and some loot to take home.

Spend Saturday surrounded by nature at the Coastal Discovery Museum. Set on 68 acres, explore nature trails, gardens, and a butterfly enclosure. Kick it old school at the Kids Zone by dressing up in costumes from Colonial days and learning about the culture and history of the island. Your kids will be having so much fun; they won’t even realize it’s so educational! Before you have to head out on Sunday, spend a low-key morning at one of our beautiful beaches. Build some sand castles, play in the surf, and enjoy some real quality family time.

Searching for even more things to see and do on Hilton Head Island this fall? Take a look at all of the great, upcoming events and happenings on our event calendar (the Connect Calendar), and start planning your perfect weekend getaway.

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Find Your Island Time

Hilton Head is America’s favorite island, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. Enjoy easy days relaxing in the sun, sand and surf on some of the best beaches in the country.
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