Just Ask Jim: Ride Smart During Hilton Head’s Hottest Days
May 26, 2026
With miles and miles of beaches, Lowcountry vegetation from palmettos to magnolias, and fascinating wildlife like dolphins, pelicans and sea turtles, it’s no surprise that Hilton Head Island is an ideal location for a summer holiday. As a Gold Level Bicycle Friendly Community named by the League of American Bicyclists, visitors can experience it all while going to and fro on two wheels.
To help you make the most of your Hilton Head summer stay, here’s a quick roundup of the not-to-miss activities you can enjoy during June, July, and August.
Outdoor Music, Art & Entertainment
Coordinated by Nash Gallery the Hilton Head Island Art Festival at Shelter Cove Harbour & Marina, a weekend event welcoming more than 50 artists in a variety of mediums like painting, pottery, jewelry, and photography. This celebration of art, shopping, dining, and entertainment is free to attend and takes place Friday, May 22 through Sunday, May 24.
HarbourFest at Shelter Cove Harbour & Marina revs up the summer every week with live music, arts & crafts, fun for kids, and fireworks. Entertainment includes the Shannon Tanner Family Show, Cappy the Clown, and Parrot Palooza. It starts Memorial Day Weekend, and the party keeps going until Labor Day Weekend. Summer offers many different performances and celebrations, so be sure to keep an eye on the schedule.
A literal Hilton Head legend, Gregg Russell can be found most evenings during the summer beneath the Liberty Oak in Harbour Town providing concerts. It’s just the spot where he has entertained children and adults alike for nearly four decades.
Bike on over to the family- and pet-friendly Hilton Head Community Market on Saturdays from 9:30 a.m. to 12:30 p.m. You’ll find a variety of vendors offering culinary delights, arts & crafts, fresh produce, and more with the chance to discover something new each week.
Shelter Cove Towne Center offers family-friendly outdoor events two evenings a week. Summer Jams kick off Tuesday, June 9 with bounce houses, face painting, and fireworks. Then on Fridays from June 19 to Aug. 7, you can enjoy live music at Sunset Celebration. But that’s not all – let’s just say that Shelter Cove really knows how to celebrate summer.
In June and July, Party in the Park on select Thursdays in Lowcountry Celebration Park includes live music – from The Chiggers, Patrick and the Starfish, The DD Band, and The Southern Heat Band – bounce houses, a dedicated car show, food truck fare, and refreshing beverages.
Let’s Get Physical
At the eco-friendly beach resort Palmetto Dunes, summer means Turtle Trots, held weekly May 27 through Aug. 12 at 8 a.m. This 5K is more of a fun run than a competition and a great way for families with kids of all ages to get active together and raise money for Palmetto Dunes Cares.
Change your perspective by starting your day at the beach practicing your asanas. Hilton Head Beach Yoga is in session Wednesdays and Saturdays at 8 a.m. at Omni Oceanfront Resort. Or this year, hit the sand on Sundays at 8 a.m. for Beach Pilates!
Book an excursion from the Harbour Town Yacht Basin and get your fish on. Whether you’re looking for a serious catch or a less competitive experience, you can’t help but enjoy a lovely island day on the water.
Tee up! Hilton Head is known for its excellent golfing, but you don’t need to be a pro to enjoy a course. First Tee is a public course with a six-hole par 3 and full-size driving range. The Learning Center is open to everyone, and First Tee also has a nine-hole disc golf course. But if you’re looking for a course with even less formality, you’ll find country club-style mini golf at Legendary Golf or a (buried) treasure experience at Pirate’s Island Adventure Golf.
From fireworks and live music to an early-morning beach workout or a family bike ride, Hilton Head delivers on summer fun. Just remember to leave some space on your calendar for relaxing on the beach!
