Roll Into Some Live Music

Roll Into Some Live Music

Hilton Head Island offers a seriously wide variety of activities and entertainment, and for anyone who enjoys live music, this is the island to be on. 

Case in point – our very own Jim “Homerun” Hall, owner of Hilton Head Bicycle Company, bike rider, avid golfer, and bass guitar plucker. He’s a member of two well-known local bands— Chilly Willy and WGB — which means he can be found at local hotspots providing the rhythm for live performances in any season. 

Ready for some tunes? Here’s a schedule highlighting live music on Hilton Head Island, specifically upcoming Chilly Willy and WGB performances this summer and into the fall. 

Chilly Willy will bring jazz, blues, and rock ‘n roll to gigs at these great venues:

Located on the island’s south end, Local Legend Brewing Company celebrates the rich history of Hilton Head’s early days in the 1970s and 1980s through its food, music, and storytelling. 

• July 5 at Local Legend Brewing Company 7-10 pm

• July 12 at Local Legend Brewing Company 7-10 pm

• July 18 at Local Legend Brewing Company 7-10 pm

• August 9 at Local Legend Brewing Company 7-10 pm

Open since 2006, The Black Marlin Bayside Grill offers fresh seafood, delicious hand-cut steaks, and obviously great music!  

• July 10 at The Black Marlin 6-10 pm

• August 28 at The Black Marlin 6-10 pm

• September 19 at The Black Marlin 6-10 pm

• October 10 at The Black Marlin 6-10 pm

At Brother Shucker’s, you’ll find great food, good times, and excellent local talent.

• July 25 at Brother Shucker’s 9 pm – midnight 

• August 22 at Brother Shucker’s 9 pm – midnight 

• September 26 at Brother Shucker’s 9 pm – midnight 

• October 24 at Brother Shucker’s 9 pm – midnight 

• November 28 at Brother Shucker’s 7-8 pm and 9 pm – midnight 

The Shipyard Beach Club performance and event venue features a deck, a gazebo, and a beautiful view of the Atlantic Ocean. 

• September 5 Shipyard Beach Club 5-8 pm

Get ready to dance! The high-energy WGB band hits the stage with the biggest disco hits of the ’70s, ’80s, and beyond, delivering the ultimate throwback party. Catch one of these live performances:

Kind of Blue was established in 2022 in the south end of Hilton Head Island and offers nightly entertainment from some of the best local entertainers, including specialty events throughout the year. 

• September 24 at Kind of Blue 7-10 pm.

Poseidon has become the mid-island destination for dining, shopping, and entertainment. And at the Rooftop Bar, dancing the night away is expected.  

• October 17 at Poseidon Roof Top 7-10 pm

Bike Safety 101: Three Essential Tips

Bike Safety 101: Three Essential Tips

When was the last time you ruminated on the safest way to ride a bicycle? If you thought bike safety was just for kids, think again. Whether you choose to pedal or go for a smooth electric ride, it’s important to start off on the right foot with reliable equipment, knowledge of the road rules, and strategies for negotiating traffic of any type.

Here are some strategies for making every ride the safest it can be.  

Just the Right Fit

Start your safety check by choosing the right bike. That means, it should be the correct size for your height, be current on maintenance, and easy for you to maneuver.

If you are attaching a basket, a child seat, a kiddie cart, an alley cat, or other extras, make sure you are comfortable riding with these items. We offer all these options with our rentals and perform ongoing maintenance checks on all equipment (including the bikes, of course). What’s more, our experts will fit you with a perfectly sized bicycle and seat height. That means, you’ll feel completely confident rolling around Hilton Head Island with any gear we provide. 

Helmet Hair: Don’t Care

OK, this is a big one. According to the National Highway Traffic Safety Administration (NHTSA), “Every bike ride begins with putting on a helmet.” Notice, the directive doesn’t mention “some bike rides” or “long bike rides.” The language is clear – you must wear a helmet any time you sit on that bicycle seat and start moving.

Next, you’ll want to make sure that protective helmet fits perfectly. Check it every time. We can help with that too. We’ll find you just the right helmet size and get it fitted properly for your unique head.

Rules of the Road

Hilton Head Island is especially friendly to bicyclists, and there are many trails and safe places to ride. But you’ll still want to keep defensive riding in mind, as you stay aware of any vehicle traffic around you. It’s your responsibility to look out for pedestrians too!

While intersections might seem like the biggest concern, according to the CDC, sections of roads away from intersections are actually more dangerous because these are areas where drivers tend to increase speed.

There are many actions you can take to increase your safety on the road whether you are biking along a street or on a dedicated bike path. Use lighting just like you would in a car – before dawn, after dusk, and in cloudy or inclement weather. Consider wearing reflective or fluorescent clothing to be more visible and use a bell to audibly alert others of your presence. Keep an eye out for obstacles like branches on the path, other riders, or opening car doors.

Other driving behaviors bicyclists should mimic include not biking under the influence, obeying street signs and signals, avoiding texting or looking at a screen, and maintaining a reasonable distance from other traffic – both the two- and four-wheel kind.

Just remember, safety is smart, helmet head is cool, and you’ll be on a roll.  

Bike-Friendly Communities Lead the Way

Bike-Friendly Communities Lead the Way

It’s always an honor to be recognized by your own industry, which is why at Hilton Head Bicycle Company, we were thrilled to earn a Silver Award from the League of American Bicyclists, which named us as an official Bicycle Friendly Business.

This award means we’ve joined more than 1,300 local businesses, government agencies, and Fortune 500 companies across the U.S. in transforming the workplace to be more welcoming to customers and employees who bike. We know that biking supports the health and well-being of our community, but for us, that’s just the start.

Surely, it’s no surprise that we consider biking a way of life. You could even say it’s our purpose for existing. In addition to fully supporting our team when they hop on two wheels to get to work, we provide thousands of Hilton Head Island visitors with the perfect ride each year through our rentals of cruisers and e-bikes. And for anyone seeking a more permanent relationship, we also offer the largest selection of traditional and electric bikes.

Considering that bicycles are so near to our hearts, we love knowing that hundreds of businesses and organizations throughout the country are united in a commitment to transform workplaces by encouraging employees and customers to bike and providing amenities to make it easier.

Whether someone chooses to ride a regular bicycle or an e-bike, the benefits are many — we’re talking about a lower carbon footprint, better health and more face-to-face interactions with others in the community, to name just a few positive effects.

We hope you’ll join us in supporting biking programs like these!  

5 Picks for Entertaining the Kids This Summer in Hilton Head

5 Picks for Entertaining the Kids This Summer in Hilton Head

There’s no question that Hilton Head makes an excellent choice for a family vacation. With beaches, parks, amazing flora and fauna, plenty of outdoor activities and so many excellent places to ride a bike, visitors of all ages will enjoy spending days or weeks here.   

We’ve already shared some suggestions for local summer recreation, from outdoor festivals [here] to cultural institutions [here], and most of them are fun for the whole family. But here are a few more, and these are geared especially for children. 

When it comes to getting hands-on, The Sandbox, an interactive children’s museum, has plenty to offer like STEM Alley, kinetic sand tables, a model flight deck, a shrimp boat, and plenty more. The museum also offers puppet shows, science experiments, interactive story time, and reptile meet & greets throughout the summer. https://thesandbox.org/

Every child gets to join in at Rick Hubbard’s Great American Kids Show at the Liberty Oak Tree in Harbour Town on summer Wednesday evenings. This show combines music, comedy, and kazoos – it’s truly one of a kind! https://www.seapines.com/experiences/events/rick-hubbards-great-american-kids-show  

The Liberty Oak Tree gets quite a lot of attention during summer, and DJ Alan will take the “stage” underneath it on Friday, June 7 and 20 at 8 p.m. His show includes a hula hoop activity for kids and is filled with surprises, right up to the giant dance party that closes out the night. https://www.seapines.com/experiences/events/dj-alan-family-show 

Movie Nights in Shelter Cove Community Park are just right for young audiences. Catch family faves like “Inside Out 2,” “Despicable Me 4,” “Mufasa: The Lion King,” “Encanto,” and others. Head to the park each Thursday from June 12 to Aug. 14 at 8:30 p.m. https://www.sheltercovetownecentre.com/events/2025/6/12/movie-nights 

Party with Stinky Pete aboard the Pirates of Hilton Head Black Sparrow pirate ship mini cruise. This 90-minute tour includes “tattoos,” pirate names and costumes, shooting water cannons, and treasure for all. That’s no scuttlebut, ya landlubber! https://piratesofhiltonhead.com/ 

Cool + Creative Summer Activities in Hilton Head 

Cool + Creative Summer Activities in Hilton Head 

Did you know Hilton Head has a lot to offer in history and culture? In addition to cruising around on bicycles and e-bikes, we love exploring the stories about our island community, enjoying its art and crafts, and sometimes even engaging in a bit of supernatural exploration.  So we’ve pulled together some of our favorite ways to get to know Hilton Head  a bit better — past, present and future. 

Arts, Culture & History 

Artworks in oil, acrylic, pastel, mixed media, and more by 100+ artists from throughout the country are on exhibit at 2025 Biennale, the 29th national juried exhibition. It’s the longest-running of its kind in the area and takes place at Art League Gallery at Arts Center of Coastal Carolina through June 13. https://www.artleaguehhi.org/ 

Head to the Lowcountry’s home for nature, art, history, and culture, the Coastal Discovery Museum at Honey Horn. This 70-acre property features exhibits, trails, and educational events. It’s free to visit, or you can head to one of the special summer programs like the Blue Crab Discovery, the Gullah Heritage Trail Tour, Kayaking Tour of Jarvis Creek, or the Dolphin & Nature Cruise. https://www.coastaldiscovery.org/ 

Sure to catch your eye from afar, the Harbour Town Lighthouse Museum is both a beacon and a landmark. Head up the 112 steps to take in incredible 360-degree views from the top or learn about the 50-year history on a Lighthouse Legends Tour.  https://harbourtownlighthouse.com/ 

Beneath Your Feet – Hilton Head’s Forgotten History Through Historic Maps, held at USCB Hilton Head Island Campus, rediscovers lost history and traces the development of the island through more than 300 historic maps. This talk is offered by Joe Grondalski on Wednesday, May 28 at 1:30 p.m. Additional dates are available. 

Something Spooky

Did you know Hilton Head has a haunted cemetery? It’s said the spirit of 19th-century William Baynard still haunts the empty Zion Cemetery mausoleum where his wife and treasure once lay. Visit on a sunny summer’s day to chase the ghosts away from what is the island’s oldest existing structure. https://www.hiltonhead.com/hilton-heads-haunted-cemetery/

Get the stories behind the ghost on a paranormal tour of Hilton Head, Daufuskie Island, and the nearby waterways. A Ghost Ship Cruise featuring haunted tales of the Lowcountry is a comfortable way to take an afterlife adventure. https://www.vagabondcruise.com/ghost-ship-cruise/ 

How to Get Out and Have Fun in Hilton Head This Summer

How to Get Out and Have Fun in Hilton Head This Summer

It’s no surprise that we think the best way to spend every day is cruising around and taking in the sights from the seat of a bike. But in between touring the island and feeling the wind on your face, there is plenty to do and see whether you’re interested in live music, shopping, or something sportier. Here are just a handful of ideas for how to spend your time on Hilton Head Island this summer. 

Music & Outdoor Parties 

Nash Gallery and The Shelter Cove Merchants Association present the Hilton Head Island Art Festival, a weekend event welcoming more than 50 artists in a variety of mediums like painting, pottery, jewelry, and photography. Taking place along the Shelter Cove Harbour & Marina, the celebration of art, shopping, dining, and entertainment is free to attend and takes place Friday, May 23 through Sunday, May 25. https://www.hiltonheadartfestival.com/

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. With so many different performances and celebrations, checking the website is the best way to plan your visit: https://www.sheltercoveharbourfest.com/

Beneath the Liberty Oak in Harbour Town, Gregg Russell is known locally as a “Sea Pines classic.” He’ll be found most evenings during the summer providing concerts just where he has entertained children and adults alike for more than three dozen years. http://greggrussell.com/

Bike on over to the Hilton Head Community Market Saturdays from 9:30-12:30 at Shelter Cove Community Park. You’ll find more than 40 vendors each week. And if you’re in town, be sure to visit Christmas in July on July 26. https://www.hhicommunitymarket.com/  

Shelter Cove Towne Center offers family-friendly outdoor events two evenings a week. Summer Jams kick off Tuesday June 10 with bounce houses, face painting, and fireworks. Then on Fridays from June 13 to Aug. 15, you can enjoy live music at Sunset Celebration. https://www.welcometosheltercove.com/

In June and July, Party in the Park on select Thursdays in Lowcountry Celebration Park includes live music, bounce houses, a dedicated car show, and food truck fare. https://www.islandreccenter.org/events/party  


Sports, Fitness & Well-Being

At the eco-friendly beach resort Palmetto Dunes, summer means Turtle Trots, held weekly May 29 through Aug. 13 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. Each Wednesday evening, the organization also offers educational Turtle Talks at 8 p.m. https://pdpoa.org/community/pd-cares/#eco 

Start your day at the beach and get a new perspective, like downward or upward dog. Hilton Head Beach Yoga is in session Mondays, Tuesdays, Thursdays and Fridays at 8:30 a.m. at Hilton Beachfront Resort & Spa Hilton Head Island and Saturdays at 9 a.m. at Omni Hilton Head. https://www.artofmassagehiltonhead.com/beach-yoga 

If you’re feeling adventurous, a fishing charter might offer your ideal activity. There are several excursions available from the Harbour Town Yacht Basin, whether you’re looking for a serious catch or a less competitive experience enjoying time on the water. https://www.seapines.com/experiences/marina 

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. https://firstteelowcountry.org/ But if you’re looking for a course with even less formality, you’ll find country club-style miniature golf at Legendary Golf or a (buried) treasure experience at Pirate’s Island Adventure Golf.