Mayor Alan Perry will join The Outside Foundation and local students for a morning of Kids in Kayaks, a hands-on environmental education program that takes learning out of the classroom and onto the waters of the Lowcountry.

Through kayaking and exploration of our salt marsh ecosystem, local middle school students get an up-close look at the waterways, wildlife and natural resources that make Hilton Head Island home, while learning why protecting them matters.

What began with approximately 400 students from three schools has grown to reach more than 1,100 students from 14 Beaufort County middle schools, an investment in environmental education and the next generation of Lowcountry stewards.

Mayor Perry is proud to spend the morning with students, educators and volunteers who are helping ensure that caring for our Island is something the next generation learns by experiencing it firsthand.

Please note: Kids in Kayaks is a school-based educational program and is not open to the general public.

Long before he was singing on rooftops, Nick Poulin was sitting in a classroom at The Children's Center. On Wednesday, October 21st, he'll return to the organization that helped raise him, taking the stage at Poseidon Rooftop, one of Hilton Head's premier entertainment venues -- as one half of beloved local band Pretty Darn for the return of Concert for the Kids, one of The Children's Center's signature annual fundraisers.

Doors open at 5:30 PM, with the concert running from 6:00 to 9:00 PM. Since forming in 2016, Pretty Darn has captivated Lowcountry audiences with an infectious blend of pop, folk, and reggae. Singers, songwriters, and multi-instrumentalists Kyle Wareham and Nick Poulin bring rich harmonies and signature dual vocals to every performance, and chances to catch the full duo together are rare, making this homecoming show a genuinely special night, both for fans of the music and for anyone who believes in what a strong early childhood program can do for a kid.

Tickets are just $25 and every single one sold makes an immediate, tangible difference, directly supporting The Children's Center's mission to provide high-quality early education and care to the families who need it most. Guests can also try their luck in a raffle featuring baskets filled with local favorites and staycation experiences, with all proceeds benefiting The Children's Center.

More than just a concert, this event is a celebration of community and a powerful opportunity to support The Children's Center's mission. As one of our primary annual fundraisers, Concert for the Kids plays a vital role in sustaining and expanding our programs, ensuring every child in our care has the chance to learn, grow, and thrive.

Mayor Alan Perry will be attending the 16th Annual Hilton Head Island Italian Heritage Festival, a favorite fall tradition celebrating Italian culture, food, family and community.

Hosted by the Italian-American Club of Hilton Head Island, the festival brings the “Old Country to the Lowcountry” with traditional Italian foods, live music from the Hilton Head Big Band, local arts and crafts, a kids’ zone, silent auction, grape-stomping and pizza-eating contests, and plenty of activities for the whole family.

Proceeds from the Italian-American Club’s fundraising efforts help support local charities and scholarships throughout the Lowcountry.

The festival is held rain or shine. Tickets are $8 per person, with free admission for children under 10 and free parking.

Mayor Alan Perry will participate in the Hilton Head Island Mayoral Candidate Forum hosted by the League of Women Voters of Hilton Head Island–Bluffton Area.

The forum will give residents an opportunity to hear directly from the candidates about the issues facing Hilton Head Island, their priorities for the community and their perspectives on the decisions ahead.

Alan looks forward to the conversation and to sharing his perspective on the work of the past four years, the challenges and opportunities ahead, and his vision for Hilton Head Island’s future.

Residents are encouraged to attend, stay informed and take part in the conversation as our community prepares for Election Day.

Stop by HHI Builders for a casual lunchtime meet & greet with Mayor Alan Perry.

Join us from 11:00 AM–1:00 PM to say hello, ask a question and spend a little time talking about Hilton Head Island and the community we all call home.

Come by when you can, we’d love to see you!

Kick off Jeep Island weekend at the Friday evening meet-and-greet at Lincoln & South Brewing Company. Mayor Alan Perry is scheduled to stop by as Jeep enthusiasts gather ahead of Saturday’s main event.

Mayor Alan Perry will participate in the 2026 Political Candidates Forum, presented by the Hilton Head Island/Bluffton NAACP Branch 5525 Political Action Committee.

This nonpartisan community forum brings together candidates for state and local offices for an informative evening focused on issues affecting Hilton Head Island, Bluffton and the surrounding area. Invited candidates include those seeking offices in the South Carolina State Legislature, Beaufort County Council, Beaufort County Board of Education, county offices, Hilton Head Island Mayor and Hilton Head Island Town Council.

The evening provides community members an opportunity to hear directly from candidates as they discuss their candidacies and respond to questions about issues relevant to the offices they are seeking.

Thursday, October 8, 2026 | 5:30–8:45 PM
Central Oak Grove Missionary Baptist Church
161 Mathews Drive
Hilton Head Island, SC 29926

The forum is sponsored by the NAACP, NIBCAA, Beaufort County Chapter National Panhellenic Council, Native Island Leaders Group, and Local African American Ministerial Alliance.

Residents are invited to hear from the candidates for Mayor of Hilton Head Island and learn where they stand on issues affecting the community.

Join Mayor Alan Perry for a casual meet and greet hosted by Outside Hilton Head.

Stop by, say hello and spend some time talking about Hilton Head Island, where we’ve been, what’s ahead and the issues that matter most to you. This is an opportunity for neighbors to connect directly with Alan, ask questions, share ideas and have an open conversation about the community we all call home.

A special thank you to Outside Hilton Head for opening its doors and bringing people together. We hope you’ll join us!

Help kick off Fire Prevention Week with a free, family-friendly pancake breakfast featuring pancakes and sausage, children’s games and prizes, a visit from Sparky the Fire Dog, and an up-close look at fire trucks and ambulances. Mayor Alan Perry is scheduled to attend.

Mayor Alan Perry will be attending the 4th Annual Hilton Head Island Rhythm & Brews, a fall celebration bringing together live music, local flavor and more than 100 beer, wine and spirit tastings at Shelter Cove Community Park.

Presented by the Hilton Head Island Wine & Food Festival, this year’s event features live music from Exit 8 and supports Ales for ALS, helping raise funds for critical ALS research.

This is a ticketed, 21+ event.

Celebrate Gullah Geechee culture through live music, visual and performing arts, handcrafted goods and Lowcountry cuisine at the family-friendly Fish & Grits Music Festival. Mayor Alan Perry is scheduled to attend.

Join Mayor Alan Perry at First Thursday Artisan Alley, a community evening featuring local artists, live music, food and the opportunity to support local makers and causes at The Shops at Sea Pines Center located at 71 Lighthouse Road.

Pull up a chair, grab a drink and join Mayor Alan Perry for a relaxed happy hour at one of the north end’s favorite neighborhood spots, Mixx on Main.

This isn’t a speech or a formal forum. It’s an opportunity to have a real conversation about Hilton Head Island: what we’ve accomplished together, the projects underway today, and the work still ahead.

Come talk with Alan about the issues that matter to our community, from land preservation and protecting the character of our Island to thoughtful growth, infrastructure, quality of life and the priorities that will shape Hilton Head over the next four years.

Bring your questions, your ideas or simply stop by to say hello. Enjoy the easygoing atmosphere at Mixx on Main and spend some time talking about the place we all call home.

Good conversation. Good company. And a chance to talk about what’s next for Hilton Head Island.

No formal agenda. No podium. Just coffee and conversation.

Mayor Alan Perry will be spending the morning at a local coffee shop, making time for anyone who would like to stop by, ask a question, share an idea or simply talk about what matters to them and the future of Hilton Head Island.

Rooted Conversations is an opportunity to connect with Alan in a relaxed, personal setting—one neighbor and one conversation at a time. Come for a few minutes or stay for a cup of coffee. He would genuinely enjoy hearing from you.

Mayor Alan Perry will join the Rotary Club of Hilton Head Island–Van Landingham for “Our Community in Focus: An Update from the Mayor.” He will share an update on the Town’s current priorities, the progress being made across Hilton Head Island and the work still ahead, from protecting our quality of life and natural environment to planning responsibly for the Island’s future. This conversation offers an opportunity to hear directly from Mayor Perry about the decisions shaping our community today and his continued commitment to keeping Hilton Head Island a place we are proud to call home.

Mayor Alan Perry will join sailors, organizers and spectators at Coligny Beach for the final day of the 2026 Formula 18 Americas Championship. Hosted by the South Carolina Yacht Club, this international regatta brings top Formula 18 catamaran teams to Hilton Head Island for four days of high-speed racing on the Atlantic.

Mayor Perry looks forward to welcoming competitors and celebrating an event that showcases Hilton Head Island’s natural beauty, maritime tradition and ability to host world-class sporting events.

No formal agenda. No podium. Just coffee and conversation.

Mayor Alan Perry will be spending the morning at a local coffee shop, making time for anyone who would like to stop by, ask a question, share an idea or simply talk about what matters to them and the future of Hilton Head Island.

Rooted Conversations is an opportunity to connect with Alan in a relaxed, personal setting—one neighbor and one conversation at a time. Come for a few minutes or stay for a cup of coffee. He would genuinely enjoy hearing from you.

Mayor Alan Perry will help welcome sailors and guests to Hilton Head Island for the Opening Ceremony of the 2026 Formula 18 Americas Championship at SlowCountry BBQ & Grill.

Hosted by the South Carolina Yacht Club, the championship brings competitors to Hilton Head for a week of racing on our local waters from September 19–25.

Mayor Perry looks forward to joining Dr. Joe Tobin, event organizers and competitors as they kick off the week and to welcoming visiting sailors to our Island on Monday, September 21st at 6:00pm. Hope to see you there!

I’m honored to be included in the Republican Women of Southern Beaufort County’s luncheon at the Old Oyster Factory. I look forward to joining fellow candidates and community members for a thoughtful conversation about how far Hilton Head Island has come, the work still ahead and the decisions that will shape our shared future.

These conversations are an important part of the election process, and I’m grateful for every opportunity to listen, answer questions and talk openly about where we’ve been—and where we’re going together.

Mayor Alan Perry is scheduled to join members of the local Latino community for a conversation at Nala’s Beach Bar & Grill. Additional program and attendance details have not yet been posted publicly.

Mayor Alan Perry will be out at the Lowcountry PaddleFest Saturday morning, joining paddlers, families and supporters for a weekend that celebrates one of the best parts of life on Hilton Head Island: getting outside and on the water.

Presented by OluKai and benefiting The Outside Foundation, PaddleFest brings together the paddling community for races and events on our local waters, while helping support programs that connect young people with the Lowcountry environment.

Come out, enjoy the morning and say hello to Mayor Perry while supporting an organization doing important work for our island and the next generation.

PaddleFest takes place September 12th @ 8:00 AM

A Conversation with Mayor Alan Perry at TidePointe

Join Mayor Alan Perry for a relaxed meet and greet and an opportunity to talk about Hilton Head Island—where we’ve been, what we’ve accomplished together and the work still ahead.

Over the past four years, Alan has worked alongside Town Council, Town staff and our community to address the issues that matter to Islanders while protecting the character and traditions that make Hilton Head such a special place to call home. This gathering at TidePointe is an opportunity to hear directly from Alan about that work and his vision for another term, but just as importantly, it’s a chance for him to hear from you.

Come with your questions, ideas and concerns and join us for a thoughtful conversation about continuing to move Hilton Head Island forward while remaining rooted in the values and traditions that have shaped our community.

Our Home. Our Community. Our Future.

Join Mayor Alan Perry as we officially kick off the campaign for re-election with an evening rooted in the community we all call home.

Stop by Lincoln & South Brewing Company to meet Alan, catch up with neighbors and hear more about the work accomplished over the past four years, and the momentum he hopes to carry forward for Hilton Head Island.

We’ll have campaign stickers, information about volunteer opportunities and plenty of ways to get involved. More importantly, this is a chance to simply spend time together. Bring your questions, your ideas and your perspective on the Island we love and the future we’re building together.

Whether you’ve supported Alan from the beginning or simply want to learn more, we hope you’ll join us as we kick off the campaign with good conversation, familiar faces and a shared commitment to Hilton Head Island.

For more than four decades, Mike Kavanaugh helped provide the soundtrack to life on Hilton Head Island and throughout the Lowcountry. A gifted guitarist, singer and entertainer, Mike became a familiar face, and unmistakable voice, at restaurants, resorts, celebrations and gathering places across our community. As a solo performer and longtime member of Jo Jo Squirrel and the Homepickles, Mike shared a remarkable range of music with generations of Islanders and visitors. He founded Jo Jo Squirrel in 1999 as the house band for Hilton Head’s Tiki Hut, and his music could be heard everywhere from Coligny and Harbour Town to weddings, oyster roasts and community celebrations.

But Mike’s impact extended well beyond the stage. He was known as a mentor and friend to fellow musicians, encouraging others in their careers and helping strengthen the community of artists and entertainers that has long been such an important part of Hilton Head Island.

On Sunday, August 16, local musicians, friends and members of the community will come together at FISH Casual Coastal Seafood to celebrate Mike’s life, music and the legacy he leaves behind. It is a fitting opportunity for Hilton Head Island to honor someone whose music was woven into so many memories made here.

All are invited to come celebrate Mike, share in the music and remember a life that gave so much to our Island.