Outbound Collective logo

Charming towns in the South for your next winter getaway

Don't sleep on the South when planning your next winter escape! These laid-back towns have real charm and opportunities to relax, shop, dine, recreate outdoors, and get in the holiday spirit. Be gone, winter blues!

By: The Outbound Collective + Save to a List


Bay St. Louis, Mississippi

Photo: 200northbeach.com

Kick back and relax in the easy-going town of Bay St. Louis, Mississippi located in Hancock County. Just 90 miles east of New Orleans, Bay St. Louis features marshland, river, and Gulf of Mexico beaches. Visit the Old Town for a plethora of different shops, art galleries, and restaurants. 

Try The Blind Tiger for burgers and hand-cut fries or the 200 North Beach Restaurant and Bar, the first restaurant to open on the Bay, for fresh seafood and mouth-watering steaks. 

The Mockingbird Cafe, also known as "the bird" is just around the corner from Old Town Bay St. Louis. It’s a cute and welcoming coffeehouse by day, but transforms into a restaurant with a pub at night! They have a selection of fun drink options like the Bird Brew Martini. 

Bay St. Louis is the right place for a relaxing, lowkey, and charming southern winter escape. Visit in December to catch the Harbor Lighting, where you can see Christmas decorated boats in the water!

Nearby Adventures: Bogue Chitto Louisiana River Float, Tammany Trace Trail, Big Branch Marsh National Wildlife Refuge

Chincoteague, Virginia

Photo: saltwaterponytours.com

For a truly memorable winter getaway, head to Chincoteague located in Virginia’s Eastern Shore region. It’s home to the Chincoteague National Wildlife Refuge, which features beautiful beaches and the best part…wild ponies! 

The area is well known for herds of wild ponies roaming around. For a more up-close encounter with the ponies and other wildlife (remembering to always be cautious and respectful), try out a saltwater pony tour via boat! It’s a memory you’ll cherish forever. 

While visiting this low-key town, you won’t be disappointed by the abundance of wildlife or the natural beauty of windswept dunes along the Assateague National Seashore. 

There is no shortage of seafood restaurants to choose from in this area. Check out Don’s Seafood Restaurant for tasty local seafood and nightly music and dancing. Stay in a Victorian-era style house at Miss Molly’s Inn! Here, you can enjoy high tea in the afternoons, making you feel like you’ve been transported to a new time and place.

Nearby Adventures: Photograph the Assateague Lighthouse, Island Nature Trail, Saltwater Pony Tours, The Bike Depot, Assateague Adventures Kayak Tours and Kayak Rentals

Fairhope, Alabama

Photo: Angel Madera Jr

Fairhope is a laid-back city in Baldwin County, Alabama on the shores of Mobile Bay. Few people visit in the winter, making it an ideal place for some peace and solitude. When you stroll the streets, you’ll get to take in the beauty of the oak trees along the way. 

Head downtown for a bite to eat at Panini Pete’s for delectable, made-from-scratch beignets. You won’t want to skip them! With a full stomach, check out Page & Palette, a book lover’s dream. You can get signed copies of books by local authors and even grab a cup of hot coffee at the cafe area. What better combination than a good book and beverage in hand? 

While visiting Fairhope, book a room at the nearby Grand Hotel Marriott Resort for a comfortable stay. It gets extra festive with lights and decorations galore around the holidays. Even in the warmer Southern climate, the holiday spirit is very much alive!


Nearby Adventures:
Village Point Park Trail, Bike or Run the Biloxi Bay Bridge, Photograph the Wildlife at the Davis Bayou Area, Bohemian Park, Fish River

Snowshoe, West Virginia

Photo: snowshoemtn.com

In Pocahontas County, West Virginia lies Snowshoe Mountain ski resort. It’s the perfect place for the whole family and offers tons of outdoorsy adventures. The resort’s skiable terrain spans roughly 244 acres in the Allegheny Mountains. 

The Village will remind you of a cute European ski town with several great options for dining like The Junction Ale House, Foxfire Grille, and Old Spruce Cafe and Tavern. After a long day of activity, treat yourself to an hour or two at the spa where you can take a deep breath and sink into some relaxation.

Nearby Adventures: Try skiing or snowboarding on snowshoe mountain’s abundance of ski trails, off-roading, snowshoeing, snowmobiling, and snow tubing.

McAdenville, North Carolina

Photo: mcadenville-christmastown.com

Also known as Christmas Town USA, the small town of McAdenville, North Carolina goes big when it comes to the holiday spirit. Located right near Charlotte, you can delight in the feel-good glow of more than 500,000 twinkling lights illuminating the town. It doesn’t stop there…the town is also adorned with beautifully decorated trees and wreaths. 

During the holiday season, you can take part in a multitude of festive activities like the tree lighting ceremony, a Christmas 5K, and a yule log parade with free hot cocoa and kettle corn. Does it get any better than that? 

All the walking around is sure to work up your appetite. Grab a bite to eat in the center of town at the Spruced Goose Station. Bring your family and stay nearby at The Lodge at Ballantyne, reminiscent of a cozy mountain-style hunting lodge. It’ll be a memorable trip likely to get you in the full spirit of the holidays.

Nearby Adventures: The South Fork River Trail of the Carolina Thread, The Boathouse, Hike Crowders Mountain, Fern Nature Trail, Seven Oaks Preserve Trail Loop


Cover Photo: Sara Cottle



We want to acknowledge and thank the past, present, and future generations of all Native Nations and Indigenous Peoples whose ancestral lands we travel, explore, and play on. Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!

Do you love the outdoors?

Yep, us too. That's why we send you the best local adventures, stories, and expert advice, right to your inbox.

Recent

You must visit these 4 places on a Minnesota road trip!

Lee Vue

12 Places to hike, bike, and camp near Chicago

Erica Zazo

Chasing sunsets and silver linings in Marin

Brian Heifferon