Hilton Head Autumn Events Calendar 2023 - Sunset Rentals Vacation Blog

Hilton Head Autumn Events Calendar 2023

Who doesn’t love autumn on Hilton Head? From sunny beaches, world-class golf, and outdoor adventures in nature to al fresco oceanfront dining, one-of-a-kind shopping, and coastal homes for the holidays, Hilton Head Island offers a smorgasbord of fun this fall season. 

Whether you’re seeking private access to miles of uncrowded beaches, heated pools, spacious gourmet kitchens to host family feasts – or a combination of it all – you’ll find your coastal home for the holidays and peace of mind with Sunset Rentals. 

Our on-island team has been welcoming families to spend all seasons in our luxury homes on Hilton Head Island for more than 25 years. The autumn season kick-off festivals have begun and no matter how you like to celebrate the holidays, there are fun fall festivities for the whole family on Hilton Head Island!


HILTON HEAD ISLAND AUTUMN EVENTS

The Fish and Grits Music Festival

Date: Oct 7, 2023 12:00 PM -6:00 PM

Location: Lowcountry Celebration Park94 Pope Avenue, Hilton Head Island, SC 29928

Maps & Directions

The Lowcountry Fish & Grits Music Festival brings awareness to the unique Gullah Geechee culture and its connection to the African diaspora by showcasing great musical talent and local cuisine. 

VISIT WEBSITE

Jeep Island 2023

Date: Oct 6, 2023 & Oct 7, 2023

Meet and Greet: October 6th, 4:00-7:30pm
Autonation, Hardeville
Learn More

Main Event: October 7th, 11am-3:30pm
Coastal Discovery Museum, Hilton Head Island
Learn More

After Party: October 7th, 5:30-8pm
Skull Creek Boathouse
Learn More

Jeep Raffle
You do not need to be present to win
Automatic, 94,000mi, max 850 tickets sold

1 for $50, 2 for $85

Learn more

The 13th Annual Italian Heritage Festival

Date: Saturday, October 21, 2023 11:00 am – 4:00 pm

Location: The Coastal Discovery Museum at Honey Horn.

Price: Tickets cost $6/person, free for children under 10. Purchase tickets HERE!

Parking is free.
No pets please!

This festival is a robust celebration of Italian culture with food, drinks, and live entertainment. The crowd-pleasing grape stomping contest will return as will the beloved pizza eating contest. But don’t worry, they will have some new events too, so don’t miss it! The Festival will offer a full slate of activities for locals, visitors, and kids.

A number of booths will be dedicated to traditional Italian foods, such as cheeses, breads, pasta, fish, meatballs, sausage and calzones, and delicious sweets, including Italian ice, gelato, biscotti and zeppolis – many sponsored by local restaurants. There will be a silent auction featuring an extensive selection of gift certificates to golf foursomes at our world-famous courses, area restaurants, boat cruises, spa visits, and of course, gift baskets, and a wide range of crafts, gifts, and art works on which to bid.

The 2023 Crescendo Celebration

Date: Oct 10, 2023 12:00 AM -Nov 18, 2023 12:00 AM

Various Locations, Hilton Head Island, SC 29928

Maps & Directions

The 2023 Crescendo Celebration features a plethora of unique arts and cultural programs, concerts, theatrical productions, museum and gallery exhibits, lectures, poetry readings, dance performances, historical tours, hands-on arts experiences, and educational offerings which are estimated to attract more than 10,000 people from all over the United States, Canada, and parts of Europe.

Kicking off October 10th the program will amaze and excite attendees until the curtains close on November 18th, 2023. Several marquee events are planned including performances, parties and the Hilton Head Island Concours d’Elegance & Motoring Festival.

VISIT WEBSITE

Hilton Head Island Concours d’ Elegance & Motoring Festival

Date: Nov 3, 2023 12:00 AM -Nov 5, 2023 12:00 AM

Various Locations, Hilton Head Island, SC 29928

Maps & Directions

The Hilton Head Island Concours d’Elegance & Motoring Festival, honoring rich tradition with southern flair, will curate a rare collection of automotive delights set against a distinctive Lowcountry backdrop that can only be found here. A Fine Pairing.

Designed with purpose and driven by passion since 2002. Since its inception, the Hilton Head Island Concours has continued to elevate every aspect of this unique Lowcountry lifestyle event into an art form.

VISIT WEBSITE

Hilton Head Island Lantern Parade

Date: November 18, 2023 5:30PM -8:30PM

Parade Route: Alder Lane Beach Access to Coligny Beach Park

Parade Steps Off @ Sunset (5:45 PM-ish)

Created by and featuring artist Chantelle Rytter, the Lantern Parade is a free event and an opportunity for the surrounding community and visitors to celebrate the history, ecology and people of Hilton Head Island.

The only requirement to participate is having a lantern!
Lineup for the parade begins at 5:00 p.m. at the Alder Lane Beach Access. The parade will step off at 5:45 PM, right after sunset, and travel north along South Forest Beach up to Coligny Beach Park. Spectators can watch along the beach anywhere between Alder Lane and Coligny Beach Park.

Live Music at Hurricane Bar

Date: November 18, 2023 6:00PM – 10:00PM

Admission: FREE!

Catch live music Wednesdays through Saturdays all during the fall at the Hurricane Bar attached to Black Marlin.

*Schedules are usually posted on their Facebook events page.

OYSTER FESTIVAL

All You Can Eat Event
November 10th: 5-8pm
Shelter Cove Community Park

All you can eat steamed local oysters, lowcountry boil, pulled pork, seafood chowder & chili. Drinks sold separately. Live music and good community fun!

Admission | $55, 12 and under $45, price increase by +$10 October 2


Festival Day
November 11th: 11am-5pm
Lowcountry Celebration Park

Admission $10, Children under 11 are free or view our discounted ticket packages

Includes admission to the event to enjoy live music and browse local artisan pop-up shops. Food, beverages, and kid’s activities are sold separately.

Bucket of Oysters: TBD
1lb Basket of steamed Shrimp: TBD
1/5lb Basket of steamed Shrimp: TBD

Leave a Reply

Your email address will not be published. Required fields are marked *

You Might Also Like

Monthly Vacation Guide – May 2024

Hilton Head Island is a destination for all seasons! But this month is looking better than average here in our beautiful barrier island. Hilton Head is nestled on the southern tip of the South Carolina coastline with a balmy sub-tropical climate, an average of 215 sunny days a year, and mild temps to enjoy our …

Read More

Where to Play Pickleball on Hilton Head Island

Get ready to dink and dive your way into the sensational pickleball phenomenon sweeping the shores of Hilton Head Island! Whether you’re a curious newcomer or a seasoned pickleball pro, Hilton Head Island’s pickleball scene offers an irresistible invitation to be part of a sensation that’s not just a game – but an island-wide obsession!  …

Read More

5 Best Dog-Friendly Restaurants Near Port Royal

One of the top questions on our guest’s minds when planning a vacation with their furry family members is where to find cafés, restaurants, and bars on Hilton Head Island that allow dogs.  You asked, and we listened! This month we feature the best dog-friendly restaurant near the Port Royal Resort Area and  Hilton Head …

Read More

9 Food Festivals Not To Miss Near Hilton Head, SC

Traveling to Hilton Head and want to enjoy some of the region’s most celebrated food festivals? Get ready for a culinary adventure like no other! Lowcountry cuisine is alive and well in South Carolina, and this region reflects that rich & diverse culinary history. From the cobblestone streets of historic Charleston to the beautiful sea …

Read More

Top 5 Resort Areas On Hilton Head Island

Whether you’re a beach lover, a golf fanatic, or an outdoor and nature enthusiast, the beautiful island of Hilton Head has something for everyone. From sunny white sand beaches, sparkling Atlantic Ocean waves, and Lowcountry waterways, to the lush fairways of world-class golf courses and miles of nature trails, Hilton Head Island has it all.  …

Read More

10 Remote Work Hotspots on Hilton Head Island 

The laid back Lowcountry lifestyle on the South Carolina coastline naturally blurs the lines between business, life, and leisure! Here on Hilton Head Island, you can trade your suits and ties for flip flops and tees, your daily commute for a bike ride, and your home office for an oceanfront retreat on the award-winning shoreline …

Read More

Why Spend Summer Vacation On Hilton Head Island?

It’s never too early to start planning a summer vacation and it gives the family something wonderful to look forward to all winter! Hilton Head Island is a dream-worthy vacation destination with warm South Carolina sunshine, endless stretches of sandy beaches, tranquil waterways and nature preserves abounding in wildlife, and beautiful beach rentals to call …

Read More

Top Dog-Friendly Restaurants Near Sea Pines Resort

Our team at Sunset Rentals has put together the ultimate guide to dog-friendly restaurants on Hilton Head Island. We’ve even taken it a step further so you can discover the best places to take your dog to dinner near your Hilton Head Island vacation rental. This month, we highlight the best dog-friendly restaurants near Sea …

Read More

Hilton Head Tips For First-Timers

Visiting Hilton Head Island for the first time? We’ve put together this extensive guide of the best tips and tricks to make the most out of your vacation! Whether you’re looking for an action-packed family adventure or a laid back island-style retreat, we’ve got you covered. Keep reading to find out more about our renowned …

Read More

Childcare & Babysitting Options on Hilton Head Island 

Planning a family vacation to Hilton Head Island, SC? As you prepare for your much-needed break along the stunning South Carolina shoreline, it’s important to consider the well-being and happiness of every single family member, including the little ones, elderly grandparents, and your furry best friends!  We’ve taken the pressure off your family vacation planning …

Read More

Top 10 Dog-Friendly Restaurants Near Shelter Cove

One of the top questions on our guest’s minds when planning a vacation with their furry family members is where to find cafés, restaurants, and bars on Hilton Head Island that allow dogs.  Hilton Head Island is surrounded by coastal waters and lush marshlands, so the freshest food & seafood is widely available across the …

Read More

Lowcountry Farmers Markets Not To Miss

Support local businesses here in the Lowcountry by visiting a Farmers Market to stock up on fresh groceries and new products. Whether you’re looking to pick up some dinner items for a home cooked meal in your vacation rental or wanting to bring home some knowledge and practice, a Farmers Market is the perfect place …

Read More

10 Adventure Ideas For Spring On Hilton Head Island

Hilton Head Island is the #1 island in the continental US and America’s favorite island, far from an under the radar or off the beaten path destination. Hilton Head Island is one of the most popular vacation destinations in South Carolina,- yet there are plenty of off the beaten path adventures that await during springtime!  …

Read More

Why Spend Labor Day Weekend On Hilton Head?

Soak in those last few days of summer and enjoy local events on Hilton Head Island over Labor Day Weekend. There’s no better way to celebrate than supporting local establishments, relaxing on the beach, and taking a trip to one of America’s top vacation destinations – Hilton Head Island! As summer comes to an end …

Read More

Top 5 Reasons to Stay in Port Royal

Port Royal is Hilton Head Island’s only completely private oceanfront residential community. Located at the tip of the Island, with approximately 1 mile of pristine beachfront landscapes, Port Royal Sound meets the Atlantic Ocean. Residents and vacationers alike can walk along the quietest beach on Hilton Head Island right from home in Port Royal. There’s …

Read More

Why Stay In Shipyard Plantation?

Nestled on 800 acres between Sea Pines Resort Area and Palmetto Dunes Plantation on the south end of Hilton Head Island, Shipyard Plantation is the smallest and most serene resort area on Hilton Head. Shipyard Plantation abounds in natural beauty and offers visitors a welcoming vacation retreat away from the crowds yet within easy reach …

Read More

7 Best Dog-Friendly Restaurants On Hilton Head Island

One of the top questions on our guests’ minds when planning a vacation with their furry family members is where to find cafés, restaurants, and bars on Hilton Head Island that allow dogs.  Hilton Head Island is one of the best dog-friendly vacation destinations on the East Coast with wide beaches that welcome your pup, …

Read More

6 Reasons To Explore Hilton Head This Fall

Whether you’re seeking a quieter (and more affordable!) shoulder season escape or a second summer on secluded beaches, head to Hilton Head Island this fall for a vacation on America’s favorite island, without the crowds!  Nestled on the southern tip of the South Carolina coastline, Hilton Head Island is a small coastal town with world-famous …

Read More

8 Lowcountry Day Trips From Hilton Head Island

If you’re looking for adventures beyond Hilton Head Island, look no further than this handy list of our favorite easy lowcountry day trips. The Lowcountry lands of South Carolina and Georgia are full of beautiful beaches, serene marshes, and gorgeous mossy oaks to guide you along your vacation throughout the region. Hilton Head Island is …

Read More

7 Tips for Responsible Wildlife Watching on Hilton Head

Hilton Head Island is a destination known for its stunning beaches, diverse ecosystems, and unique habitats abounding in wildlife. Whether it’s witnessing the marvel of baby sea turtle hatchlings, getting up close and personal with our beloved marine mammals, encountering alligators, or discovering Hilton Head’s best birding spots with your binocs, you’ll soon discover a …

Read More

Top 7 Reasons To Stay In Palmetto Dunes Resort Area

Hilton Head Island was named the #1 Island in the U.S. and Canada in Travel+Leisure 2021 World’s Best Awards for the 5th consecutive year! The award-winning Palmetto Dunes is one of the most well-known and popular resort areas of Hilton Head, nestled mid-island on 2,000 acres of lush oceanfront landscapes with world-class amenities, 3-miles of …

Read More

When Is The Best Time To Visit Hilton Head Island?

Hilton Head Island is a destination for all seasons! Our beautiful barrier island is nestled on the southern tip of the South Carolina coastline with a balmy sub-tropical climate, an average of 215 sunny days a year, and mild temps to enjoy our pristine beaches, serene waterways, untouched nature preserves and award-winning golf and tennis …

Read More

Top 20 Spots To Watch The Sunset On Hilton Head

The distinctive Lowcountry scenery and tranquil waterways on Hilton Head Island provide the perfect canvas for some of the most breathtaking sunsets you’ll ever witness. As the sun dips slowly below the horizon, fiery palettes of reds, oranges, pinks, and purples paint the skies casting a warm glow over Hilton Head’s white sandy shoreline, untouched …

Read More

How to Plan a Vacation at Sea Pines Resort

Sea Pines Resort is home to Hilton Head’s top attractions, the best shopping and dining on the island, world-class golf courses and tennis facilities, two marinas for watersports, nature trails for hiking and horse-riding, and 20-miles of connected paved trails for biking around the resort. 

Read More

The Ultimate Summer Guide For Hilton Head Island

Whether you’re in search of a quiet island escape or action packed summer vacation, we invite you to explore the island like a local with our inspiration for your summer vacation on Hilton Head Island. 

Read More

Romantic Date Ideas On Hilton Head Island

Hilton Head Island is always a great place for a romantic getaway, but the island gets a little more romantic at the end of season. Sunset Rentals wants to help you plan an unforgettable romantic getaway to Hilton Head this winter. To assist you, we’ve created a helpful guide on romantic things to do in Hilton Head during your trip.

Read More

10 Best Kept Secrets on Hilton Head Island

Hilton Head Island is widely-known as one of America’s favorite islands, being voted the “#1 Island in the Continental US” numerous times by Travel+Leisure. The Island is home to 24 championship golf courses, world-class tennis facilities, action packed adventures, award-winning restaurants, and beautiful beaches, but you’ll also find that Hilton Head Island also has some pretty special secrets that you won’t want to leave uncovered!

Read More

5 Tips For Hosting a Family Reunion on Hilton Head

Situated only 30 miles from historic Savannah Georgia, Hilton Head Island boasts a stunning and serene seaside location, welcoming southern charm, a relaxed Lowcountry lifestyle, and a wide range of family-focused activities and vacation homes that appeal to guests of every generation.   Not only is Hilton Head the “#1 Island in the Continental US”, but …

Read More

Top 4 Golf Courses On Hilton Head

If you’re visiting Hilton Head Island in winter and want to hit the links, where should you go? The team at Sunset Rentals has some ideas. Here’s our list of the best courses to play in Hilton Head on your winter golf trip.

Read More

9 Fun Summer Festivals On Hilton Head 2023

Hilton Head Island, SC hosts a range of popular festivals that draw many thousands of visitors to the island every year. The Island’s event calendar includes local arts, nightlife, family activities, festivals, and much more. The team at Sunset Rentals has compiled a list of our favorite upcoming events on Hilton Head Island. Be sure to check some out during your getaway to the stunning shoreline of South Carolina!

Read More

8 Best Kayak & SUP Tours on Hilton Head Island 

There are endless ways to enjoy the local waters of Hilton Head Island, but a guided kayak or SUP tour with a local naturalist is by far the most intimate Lowcountry experience available.  Hilton Head’s network of nature trails extends to miles of tranquil paddling trails that lure you away from the white sandy beaches …

Read More

16 Free Things To Do On Hilton Head Island

When it comes to planning a vacation on Hilton Head Island, visitors have an abundance of world-class golf courses, racquet clubs, nature tours, and charters to add to their itinerary, but many of the island’s best experiences can be savored without reaching for your wallet. From our wild, scenic beaches, lush waterways, and tranquil trails …

Read More

3 Bars Not To Miss On Hilton Head Island

What’s better than lounging on the beach with the sun on your skin and sand between your toes? Doing all of that with a cool drink in your hand of course! From casual beach shacks to elegant wine bars, the island has something for everyone.

Read More

Hilton Head Island Grocery Stores & Food Delivery Services

For many travelers, shopping for groceries is a fun beginning to a vacation, but for others, well it’s a burden they would rather leave behind. One of our guests’ most frequently asked questions about Hilton Head Island is where to stock up on groceries, find the freshest seafood, and fill the cooler with beverages during …

Read More

Local Tips for Hilton Head Island

As Hilton Head Island locals, we’ve got all the best local tips up our sleeve! We know all the best places for your next adventure, hidden gems you’ll otherwise pass on by, tips to make the most out of your trip, and all the best places to stay across the island. Don’t just take our …

Read More

The 5 Best Seafood Restaurants in Hilton Head Island

While South Carolina’s sandy Hilton Head Island is best known for its pristine beaches, bicycling trails, and world-renowned golf courses, there’s no denying its genuinely extraordinary culinary scene, mainly the fresh-caught seafood delicacies. With nearly five dozen seafood restaurants in Hilton Head, you have plenty of dining options to choose from! Our team at Sunset …

Read More

How To Rent Jet Skis On Hilton Head Island?

While it won’t be easy to pry your family from Hilton Head Island’s sandy beaches and pristine golf courses, there’s nothing quite like an aquatic adventure in Calibogue Sound, a salty bottlenose dolphin haven. There are countless ways to explore the Sound, including a dolphin safari, sky-high parasailing voyage, and chartered fishing trip. However, there’s …

Read More

How To Go Parasailing on Hilton Head Island?

South Carolina’s picturesque Hilton Head Island remains an aquatic wonderland, especially for those with a penchant for oceanic thrills. Within minutes of arrival, travelers can swiftly hop aboard a speedy wave runner, join a dolphin tour, and hook a jumbo Spanish mackerel deep at sea. However, nothing tops the sheer exhilaration of parasailing in Hilton …

Read More

2024 RBC Heritage PGA Tournament Guide

Hilton Head Island annually hosts the only PGA Tour Event in South Carolina for the RBC Heritage where 132 players compete for the coveted plaid jacket and a $20M purse. First held in 1969 at Pete Dye’s Harbour Town Course, this event quickly became a hit drawing in thousands of visitors each year throughout mid-April …

Read More

Top 5 Hilton Head Water Sports

There’s never an offseason for Hilton Head Island water sports, especially for those with a penchant for aquatic thrills. With mid-June rapidly approaching and businesses gradually reopening, this summer aims to be yet another glorious chapter for you and your family. To ensure that your long-awaited island escape is nothing short of flawless, we’ve compiled …

Read More

5 Dog-Friendly Activities On Hilton Head

Unquestionably, the most difficult aspect of planning a well-deserved vacation is lining up necessary pet boarding for your favorite furry friend. It’s never easy saying “goodbye” to a pet (or pets), even if it’s just for a week. However, one of the fastest-growing trends in the hospitality industry is the rise of pet travel. Instead …

Read More

Hilton Head Guide For Bird Watching

The best part about birding in Hilton Head Island, South Carolina, is that it’s an inexpensive way to get outdoors, and it’s great for every age. Hilton Head is one of the best places to visit in South Carolina for birding as our town is quite environmentally friendly, and there are hundreds of species that …

Read More

9 Dog-Friendly Delights at Coligny Plaza

Our team at Sunset Rentals has put together the ultimate guide to dog-friendly restaurants on Hilton Head Island. We’ve even taken it a step further so you can discover the best places to take your dog to dinner near your Hilton Head Island vacation rental. This month, we highlight the best dog-friendly restaurants near Coligny …

Read More

4 Rainy Day Activities On Hilton Head Island

When you vacation on Hilton Head Island the main things to do is enjoy the sun, shopping and eat amazing food. But the big question is what is there to do when it is raining outside? Don’t let a little rain dampen your Hilton Head Island vacation spirits! This place has plenty of fun-filled activities …

Read More

10 Reasons to Visit Hilton Head Island in Winter 

Hilton Head Island in winter is a well-kept secret, offering an escape filled with serenity, adventure, and a chance to explore the island’s top attractions and best-kept secrets, without the crowds or traffic jams! With its mild weather, uncrowded beaches, and a wealth of activities, you’ll wonder why you didn’t consider a winter getaway to …

Read More