Things to Do in Hilton Head, SC in May UPDATED 2026

If you’re planning a trip and looking for things to do in Hilton Head, SC in May, you’re landing in one of the best travel windows of the year. The weather is warm but not oppressive, summer crowds haven’t fully arrived, and the calendar is full of events and fun-filled activities you're sure to love. 

No matter what brings you to town—whether it’s a family trip, golf weekend, or a quick coastal reset—May hits a sweet spot. You can spend your days outside, catch live music in the evenings, and still get into restaurants without building your entire schedule around reservations.

Here’s what’s happening on Hilton Head Island in May 2026, plus a few ongoing activities to add to the itinerary.

In This Article:

• May 2026 Events on Hilton Head Island
• Recurring Events & Weekly Activities
• More Things to Do in Hilton Head, SC in May
• Book Your May Stay on Hilton Head Island
• Frequently Asked Questions

May 2026 Events on Hilton Head Island

Pedal Hilton Head Island

A scenic, non-competitive ride that’s become one of the island’s signature spring events. Pedal Hilton Head raises funds for the Boys & Girls Club while giving riders a chance to explore both Hilton Head Island and Bluffton on routes designed for all experience levels.

Event Details:

• Date: Sunday, May 3, 2026
• Location: Hilton Head Island & Bluffton routes
• Routes: 62-mile, 40-mile, 30-mile, 20-mile, 10-mile, and 2-mile family ride
• Includes: T-shirt, route support, post-ride meal
• Cost: Registration required (varies by distance)

Long Meadow Ranch Wine Dinner

A one-night dining experience inside Harbour Town, this multi-course dinner pairs seasonal dishes with wines from Long Meadow Ranch. It’s great if you’re planning a quieter evening or want something a bit more elevated than a typical dinner out.

Event Details:

• Date: May 14, 2026
• Time: 6:30 PM
• Location: Heritage Room at Harbour Town Clubhouse
• Address: 11 Lighthouse Lane, Hilton Head Island, SC
• Cost: Reservation required

Tap Takeover at Fraser’s Tavern

Held in Sea Pines, this recurring event brings in rotating breweries for an evening of tastings and conversation. It’s casual, easy to drop into, and a great opportunity to try some local and regional craft beer on the island.

Event Details:

• Date: May 19, 2026
• Time: 5 PM – 8 PM
• Location: Fraser’s Tavern
• Address: 100 N Sea Pines Dr, Hilton Head Island, SC
• Cost: Pay-as-you-go

Hilton Head Island Art Festival (Shelter Cove Harbour & Marina)

One of the bigger May events, this festival lines the waterfront at Shelter Cove Harbour & Marina with artists from across the country. You’ll find everything from fine art and photography to handmade jewelry and glasswork, plus live music throughout the weekend.

Event Details:

• Dates:
  
  • Friday, May 22, 2026: 10 AM – 6 PM
  • Saturday, May 23, 2026: 10 AM – 6 PM
  • Sunday, May 24, 2026: 10 AM – 4 PM
• Location: Shelter Cove Harbour & Marina
• Cost: Free 

Palmetto Dunes Turtle Trot 5K

A midweek race that draws both visitors and locals, the Turtle Trot 5K is a low-pressure way to get active during your trip. The course runs through Palmetto Dunes and wraps up quickly enough to still leave your day wide open.

Event Details:

• Date: Wednesday, May 27, 2026
• Time: 8 AM – 9:30 AM
• Location: Palmetto Dunes Resort
• Cost: ~$30–$35 depending on registration timing

Recurring Events & Weekly Activities

These ongoing events are easy to work into your schedule, whether you're visiting in May or another month. 

Hilton Head Island Farmers Market

Held at the Coastal Discovery Museum, this weekly market features fresh produce, baked goods, seafood, and local vendors. It's a great stop if you're looking for some island ingredients to whip up at your Beachside Getaway vacation rental. 

Event Details:

• When: Every Tuesday
• Time: 9 AM – 1 PM
• Location: Coastal Discovery Museum (Honey Horn campus)
• Cost: Free to attend

First Thursday Artisan Alley (Sea Pines)

A smaller, more local-feeling event in Sea Pines, Artisan Alley brings together artists, makers, and live music near Harbour Town. It’s a good option if you want something low-key in the evening.

Event Details:

• When: First Thursday of the month (May date varies)
• Time: 4 PM – 7 PM
• Location: Shops at Sea Pines Center
• Address: 71 Lighthouse Road, Hilton Head Island, SC
• Includes: Local vendors + live music

More Things to Do in Hilton Head, SC in May

Events are only part of the picture. May is one of the easiest times of year to actually enjoy the island without working around peak-season crowds.

Catch Live Music at Shelter Cove

Shelter Cove Harbour & Marina regularly hosts live music in the evenings, especially as the season ramps up toward summer. It’s an easy way to end the day—grab dinner nearby, then walk the marina while bands play along the waterfront.

Spend Time in Harbour Town

Between the lighthouse, shops, and waterfront views, Harbour Town is a great place to spend an afternoon or evening. 

Get Out on the Water

Boat rentals, dolphin tours, and kayaking all hit their stride in May. Water temperatures are warming up, and you can still find a last-minute adventure without needing weeks of advanced reservations and planning. 

Bike the Island

Hilton Head’s bike paths are one of its biggest advantages. With 50+ miles of paved trails and flat terrain, it’s easy to ride from your rental to the beach, Shelter Cove, or local shops without needing a car.

Book Your May Stay on Hilton Head Island

Featured Property: 1 Baynard Park

If you’re planning around these events or just want to take advantage of the timing, May is one of the easiest months to secure a great property before peak summer rates hit.

At Beachside Getaway, we offer vacation rentals across Hilton Head Island that make it easy to enjoy everything May has to offer—from quick access to Shelter Cove and Harbour Town to homes built for group stays.

Browse our Hilton Head Island vacation rentals and book direct to lock in your dates before the summer rush.

Frequently Asked Questions

Is May a good time to visit Hilton Head Island?

Yes—May offers warm weather, fewer crowds, and a full calendar of events before peak summer season begins.

What is the weather like in Hilton Head Island in May?

Expect daytime highs in the mid-80s with moderate humidity—comfortable for beach days, biking, and outdoor activities.

Are restaurants and activities open in May?

Yes. Most seasonal businesses are fully open by May, but without the long waits you’ll see in peak summer.

Are there events every week in May?

Yes—between one-time events and recurring options like the farmers market and live music, there’s something happening every week.