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16 Sep 2022
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Vacation RentalsActivities & Events

Coming to visit Kiawah Island or Charleston this fall or winter? There are plenty of fun seasonal events around the Lowcountry to enjoy. Whether you are looking for pumpkin patches or holiday celebrations, there's an event for you! Now, here's a look at some of our favorite fall and winter happenings in the area. 

Fall Events near Kiawah Island

Fall is a truly special season on Kiawah Island. With fewer crowds and cooler temperatures than the summer season, autumn is an ideal time to visit Kiawah. From fall festivals to Halloween attractions, there's an event for everyone near Kiawah Island this fall! 

Boone Hall Fright Nights 

Various nights September 24 - October 30, 2022
Prepared to be scared! Celebrate Halloween with a creepy night of fright! Boone Hall Fright Nights, Charleston's favorite Halloween event, is back for its 16th year and scarier than ever with three spooky attractions: The Lodge at Willow Ridge, Freaks World of Oddities, and Sinister CinemaBoone Hall is located in Mount Pleasant, about one hour from Kiawah Island.   

Boone Hall Pumpkin Patch

September 30 - October 30, 2022
The Boone Hall Pumpkin Patch is one of the largest fall festivals in the state, celebrating more than 20 years of family fun! Come experience all that they have to offer: hayrides, corn maze, pumpkin patch and so much more.

Legare Farms Pumpkin Patch

October 1 - October 30, 2022
Come celebrate the 20th year of the Legare Farms annual pumpkin patch! Pick a pumpkin, visit the animal barnyard, play in the playground, eat at the concession stand, shoot the corn cannon, ride the hayride, and more! 

Kiawah Island Triathlon 

October 2, 2022 > moved to October 16, 2022
Tri-Kiawah is a USAT-sanctioned intermediate distance competition featuring a 0.7-mile swim, 25.1-mile bike, and 6.1-mile run. This race is currently the only intermediate distance triathlon in the Charleston area to feature an ocean swim. Our team is very familiar with this triathlon - we've even competed in it ourselves! Each year, we look forward to hosting race participants from near and far in our Kiawah Island vacation rentals

Sea Island Cars & Coffee

October 15, 2022
Arrive in your favorite ride or come by to browse unique, antique, and other cool cars at the monthly Cars & Coffee event! Coffee and breakfast items will be available for purchase at Java Java. This event takes place on the third Sunday of every month. 

Pony Up Movie Night

October 22, 2022
Charleston Area Therapeutic Riding's 6th Annual Pony Up Movie Night is held at CATR Farms. Attendees enjoy fun games, chances to win prizes, and a showing of the feature film Flicka. All proceeds benefit CATR’s therapy horses. What could be better than a fun event that benefits a great cause? Akers Ellis is proud to sponsor Pony Up Movie Night again this year.


October 22, 2022
The annual Dogtoberfest returns to Freshfields Village! Bring your furry friends along to enjoy a fun-filled Pet Expo, complete with a pet costume contest and adoptable meet and greet. Guests will enjoy browsing pet vendors, listening to live music, and meeting local rescue groups.

Charleston Beer Week

October 28 - November 6, 2022
Back for its 9th year, much-loved Charleston Beer Week returned for a 10-day celebration of breweries and beer in the Holy City. With 50+ events, there's sure to be something for every kind of beer enthusiast.

Harvest Festival

November 5, 2022
Head on down to Johns Island County Park for live bluegrass music from local bands, hayrides, pumpkin decorating, archery, and much more. Feast on Southern delights like finger-lickin’ Carolina barbeque, kettle Korn, and all of your favorite festival foods! Be sure to check out the crafters market for some great holiday shopping!

Winter & Holiday Events near Kiawah Island

Spending the holiday season on Kiawah Island or in the greater Charleston area? Get out of the house and enjoy some of these wonderful winter events! As more winter and holiday events are scheduled, we will update this post. Be sure to check back soon!

Holiday Festival of Lights

November 11 - December 31, 2022
Each winter, thousands of friends and families create memories while driving through the Holiday Festival of Lights on James Island. Enjoy the 3-mile display of multicolored lights, then park your car to enjoy family activities like roasting marshmallows, drinking hot chocolate, shopping, and so much more! The festival runs nightly from 5:30 to 10:00 pm.

Aquarium Aglow

Select nights November 18, 2022 - December 31, 2022
The South Carolina Aquarium Aglow exhibit will get the whole family in the holiday spirit. This immersive holiday light experience will feature tens of thousands of lights as well as live entertainment. The SC Aquarium is located in downtown Charleston, about 40 minutes from Kiawah Island.

Santa Visits the Village

Select times November 25, 2022 - November 27, 2022
Kick off the festive season with Freshfields Village on Friday, November 25th as they welcome Santa to the Village Green! Santa Claus will be available for complimentary photos in Santa’s Surf Shack from 10:00 am to 5:00 pm on Friday, November 25 & Saturday, November 26 and 11:00 am to 4:00 pm on Sunday, November 27.

Uncorked - The Ultimate Christmas Holiday Event

December 2, 2022
Boone Hall Plantation and the Charleston Radio Group are thrilled to invite you to "Uncorked". This exclusive black tie optional Christmas holiday event is hosted at the renowned Cotton Dock venue at Boone Hall Plantation. This enchanting evening will include good food and drink, lovely music, and great company. 

Homegrown Holiday Bazaar

December 3, 2022
The annual Homegrown Holiday Bazaar returns to Johns Island for its ninth year! This highly anticipated holiday market will feature local vendors and artisans, food, crafts, games, and tons of festive activities for all ages. 

Drayton Hall Oyster Roast

December 4, 2022
Drayton Hall throws the best annual oyster roast to celebrate the holiday season in Charleston! All-you-can-eat oysters, a chili bar, and local beverages will ensure that you have a great time all while supporting the Drayton Hall mission. Register early; this event sells out early every year!

Kiawah Island Marathon

December 10, 2022
Now entering its 44th year, the Kiawah Island Marathon and Half Marathon starts and finishes at The West Beach Conference Center. Along the way, you’ll enjoy spectacular views of maritime forests, marshes, and grand homes. Join team Akers Ellis for a fun-filled weekend! 

New Year's Eve Family Celebration

December 31, 2022
Ring in 2023 with friends and family, featuring entertainment and fireworks. Don’t forget to stay for the fireworks starting at 9 pm. The evening is full of entertainment suitable for families and groups of all ages. Please note this event is limited to Kiawah Island guests and residents. 

Plan Your Fall or Winter Getaway

Escape the cold on Kiawah! Our Kiawah Island vacation rentals are perfect for guests who want to spend the cooler seasons near the beach. We offer an extensive variety of private home, cottage, and villa vacation rentals on Kiawah Island, and aim to provide our guests with vacation experiences to last a lifetime.