This article is sponsored by Visit Mississippi.
Mississippi is home to an abundance of charm and beauty year-round, but when fall arrives, there’s a whole new batch of fun to be had. As you map out your fall road trips, consider adding these small Mississippi towns to your route — Greenwood, Oxford, DeSoto County, Tupelo, Cleveland, Ridgeland, and Starkville. Whether you’re looking for outdoor adventure, a taste of history, or simply want to get in the Halloween spirit, there’s something for every type of traveler on this list!
GREENWOOD
Dubbed “the Heart and Soul of the Delta,” Greenwood, Mississippi, is chock-full of history and culture. In addition to helping legendary blues musician Robert Johnson get his start, this city boasts beautiful historic homes, unique shopping, and plenty of delicious dining options.
Before embarking on your getaway, plan your adventures using Visit Greenwood’s new and convenient interactive map, highlighting must-see museums, parks, restaurants, and more. You’ll be able to stay and enjoy what Greenwood has to offer and then stray to a variety of attractions within just an hour’s drive.
To soak in the local history, the Museum of the Mississippi Delta highlights Greenwood’s agricultural and military past along with rotating featured exhibits. Little ones will enjoy exploring the Children’s Discovery Room, which invites kids to shop at a local farmers market and participate in arts and crafts.
Grand Boulevard is just a short drive from the museum, a street known for its delightful array of historic homes. Named one of “America’s Most Beautiful Streets” in the 1950s, you’ll enjoy close-up views of expansive mansions and cozy cottages from different eras.
To get to Grand Boulevard, you’ll drive across the Keesler Bridge, another attraction that honors Greenwood’s history. Stretching over the Yazoo River, the bridge reminds visitors of the town’s industrial heritage.
The Greenwood area is also home to nine markers along the Mississippi Blues Trail. Local markers include Baptist Town — one of Greenwood’s oldest African American neighborhoods — and the Elks Lodge, a legendary venue for rhythm and blues music.
After a day of exploring, refuel with delicious food at any of Greenwood’s local eateries. Fan and Johnny’s is a popular spot for both lunch and dinner. Meanwhile, Giardina’s is a fine-dining staple offering a variety of seafood and pasta.
Another great option is Serio’s, an Italian steakhouse with a cozy dining room featuring a fireplace, full-service bar, and patio with a Bocce ball court.
If you’re seeking a Southern vibe that includes arts, history, culture, shopping, and great food, add Greenwood to your must-visit list. Make it a weekend or a full week Delta experience. Learn more at visitgreenwood.com.
OXFORD
Whether your idea of fall fun is enjoying a cocktail outside on a patio or embarking on a spooky ghost tour, Oxford offers something for everyone. Here are a few ideas to get you started!
Founded by local entrepreneur Jennifer Vesey, Oxford Ghost Tours is a quintessential fall activity. After researching old newspapers and books, Jennifer discovered a darker side of Oxford’s history. You can hear all about those ghostly discoveries every Thursday and Friday evening during one of her guided tours.
For a less spooky alternative, pay a visit to Chadwick Farm, offering a wide variety of farm activities like pumpkin picking, wagon rides, a petting barn, a corn maze, and more.
On the other hand, if you’re looking to take advantage of the prime fall patio weather, there are plenty of local places to choose from! Newer to Oxford’s restaurant lineup is Circle & Square Brewing, a taproom serving in-house-brewed craft beers. And if beer’s not your thing, don’t fret — they also offer specialty cocktails and light bites like pretzels, dips, and hot dogs.
For a standout lunch or brunch meal, head to Good Day Café. Founded by the same owners of local favorite Bar Muse, the café offers hearty sandwiches with fun monikers like The Turk and The Ranch Hand (pictured below). They also recently introduced a dinner service, available on Friday and Saturday evenings.
No trip to Oxford is complete without shopping your way through its Historic Square. For a bit of everything, Neilson’s Department Store offers clothing for men, women, and children, as well as home decor.
For more clothing, the Square is home to a variety of charming boutiques, including Hinton & Hinton (which also offers a women’s section!), Cicada, and Jane.
Avid readers will love spending an afternoon perusing the shelves at Square Books. The two-story independent bookstore offers a strong literary fiction section, including new reads as well as classic favorites.
The Square gets into the holiday spirit a little early, as its annual Holly Jolly Holidays event kicks off on November 23. Festivities include ice skating, visits from Santa Claus, and holiday lights galore.
DESOTO COUNTY
From its Southern charm to its rich history and opportunities for outdoor fun, DeSoto County checks all the boxes for the perfect autumn getaway. Here are some of the best things to do and see in the area this season!
Located in Hernando, Cedar Hill Farm is the perfect place to spend an afternoon with family and friends. Open from September 28 through October 30, the farm includes a pumpkin patch and corn maze. Plus, from October 4 through November 2, you can get in the Halloween spirit by enjoying one of the farm’s haunted hayrides.
While in Hernando, be sure to also visit Courthouse Square! The quintessential town square is home to a variety of charming shops, including Saint Boutique and The Square Cupboard.
Every Saturday through October 26, Hernando Courthouse Square is also home to a bustling farmers market. The market is open from 8 a.m. to 1 p.m. and hosts vendors selling everything from local produce to fresh-cut flowers and homemade crafts.
If you want to get a head start on your holiday shopping — or just want to treat yourself — Southaven’s Tanger Outlets is home to more than 50 retailers. You’ll find popular brands like Adidas, Express, Simply Southern, and Michael Kors.
Another popular destination in DeSoto County is Southaven’s Silo Square. This outdoor, mixed-use development is a one-stop shop for local restaurants and boutiques.
Before embarking on an afternoon filled with shopping, fuel up at the nearby Sippin Silo Wine Bar, which offers charcuterie boards and flatbreads in addition to 24 self-service wine taps. Lucky Dog Music Hall & Bar is another popular restaurant that is also known to host live music!
When you’re ready to start shopping, don’t miss Silo Square favorites like Dappled, Trouble Boutique, Stella Ivy, Magnolia House, and Ultimate Gifts.
TUPELO
If you’re looking for a relaxing fall getaway, Tupelo is the perfect spot to unwind and enjoy the beauty of the season. Known for its small-town charm and fascinating history, Tupelo offers a variety of activities that allow you to take in the changing scenery while exploring the area at your own pace.
A visit to the Elvis Presley Birthplace and Museum is essential for music lovers. Jump in and learn more about the King of Rock ‘n’ Roll by downloading the All Shook Up: Elvis’s Tupelo Experience passport. This free pass offers a glimpse into Elvis’s Tupelo story by taking you to 21 different landmarks, Elvis-themed eateries, and public art around Tupelo. When you complete the experience, stop by the Tupelo Visitors Center for a free gift.
Tupelo offers easy access to the Natchez Trace Parkway for those who love the outdoors. Whether you’re up for a scenic drive, a casual hike, or a bike ride, the Parkway provides plenty of opportunities to appreciate the season’s beauty.
You can also explore Tombigbee State Park, where fishing, canoeing, and nature trails offer a peaceful retreat among the vibrant fall foliage.
Downtown Tupelo is another gem during the fall months. Stroll along Main Street to enjoy browsing through local shops and experience one of the many restaurants offering seasonal Southern flavors. You can also explore the Cocktail Trail to enjoy a variety of delicious artisan cocktails at each participating downtown restaurant.
With three distinct shopping districts, Tupelo offers everything from boutiques to antiques, making fall shopping a must. Downtown is home to local shops, art galleries, and even a 119-year-old department store.
The Midtown District has the latest fashions, outlet shopping, and gift shops in the heart of the city, while the Barnes Crossing District is anchored by the Mall at Barnes Crossing, which features major national brands.
CLEVELAND
Best known for its connections to the Mississippi Delta, Cleveland offers a rich musical history, vibrant fall colors, and one-of-a-kind pottery. Here’s how to make the most of your visit!
We recommend planning your getaway around the annual 50 Nights of Lights event. From November 11 through January 1, Downtown Cleveland is transformed into a magical winter wonderland, thanks to 1,000,000+ Christmas lights and other festive decor.
Another beloved celebration, the 2024 Day of the Dead, takes place on November 2 in Downtown Cleveland. The free, family-friendly event includes a costume contest, face painting, and a free concert by the Squirrel Nut Zippers.
Music lovers will enjoy visiting the GRAMMY Museum Mississippi. In addition to permanent exhibits that explore the history of the GRAMMY Awards and the legendary Highway 61, you can also find new exhibits this fall — including Taylor Swift: Through The Eras as well as Music America: Iconic Objects From America’s Music History.
If it’s close-up views of fall foliage you’re after, there are a few nearby options. Visit the bluff at Terrene Landing to enjoy sweeping views of the Mississippi River. If you’re lucky, you may even spot a steamboat or two!
Great River Road State Park is another popular outdoor attraction, as it offers picnics, boating, fishing opportunities, and sweeping views of the Mississippi River.
Before leaving town, pick up a souvenir or two at Cleveland’s renowned pottery studios. Peter’s Pottery in Mound Bayou is known for its collection of unique, hand-crafted pieces, ranging from adorable animals to tableware, lamps, and candlesticks.
Another popular shop, McCarty Pottery in Merigold is famous for pieces that offer a distinctive style and “river stone” mark.
RIDGELAND
No matter your passion, the city of Ridgeland offers something for everyone. From seasonal events to beautiful scenery and a delicious culinary scene, here are some of our favorite things to do in this charming town.
To experience the best of fall in Ridgeland, make plans to visit its Scarecrow Trail. From now through November 26, you can visit the Ridgeland Wildflower Field & Art Park to witness a colorful display of pumpkins and scarecrows.
Another highly anticipated event, the Chimneyville Arts Festival is the perfect opportunity to cross a few people off your holiday shopping list. Offering a variety of handmade goods and crafts, the event takes place at the Bill Waller Craft Center from December 5 through 7.
If you can’t make it to the festival, don’t worry! The Bill Waller Craft Center is open five days a week and offers a variety of handmade gifts from 400+ local artists who are part of the Craftsmen’s Guild of Mississippi.
For even more retail therapy, shop along Ridgeland’s Retail Trail, home to a variety of unique shopping districts like the Township at Colony Park, Renaissance at Colony Park, Northpark, and the Railroad District.
History buffs will enjoy spending an afternoon exploring the Ridgeland History Trail. Currently home to 22 trail markers, you’ll learn about the city’s rich history by exploring local landmarks like Ridgeland City Hall, Greenwood Plantation, and the Natchez Trace Parkway.
The famous Natchez Trail Parkway runs through about eight miles of Ridgeland, so you can explore the local scenery and stunning fall foliage.
Another popular option for leaf-peeping, the Chisha Foka Multi-Use Trail is a 10-mile paved path that winds through historic Choctaw homelands. This trail is especially popular among cyclists, and Ridgeland even offers an easy-to-use Explore Ridgeland Bikeshare program. Outdoor enthusiasts seeking more adventure will love the area’s extensive mountain bike trails.
STARKVILLE
Though it’s primarily known as Mississippi’s premier college town, Starkville offers much more than football this time of year. From seasonal events to outdoor adventures and a delicious culinary scene, here are a few highlights!
One of Starkville’s most popular fall events, Pumpkin Palooza is a can’t-miss celebration. This year’s event takes place on October 24 on Main Street, inviting children of all ages to enjoy trick-or-treating alongside face painting and inflatable jumpers.
While the 2024 season of the Starkville Farmers Market has been underway since April, the fun continues through November 16. In addition to year-round favorites like arts, crafts, and baked goods, the fall iteration offers seasonal favorites like apple cider and pumpkins.
Then, on November 20 and 21, the fun continues with Starkville’s annual Holiday Bazaar. Now in its 52nd year, the shopping event hosts nearly 100 vendors every year. Plus, the 2024 market includes a Reindeer Raffle with over $5,000 worth of prizes.
To soak in the local wildlife, spend the afternoon exploring the Noxubee National Wildlife Refuge. Offering several well-maintained hiking trails, there are plenty of opportunities to enjoy the fall foliage. Popular trails — ranging from easy to moderate in difficulty — include Bluff Lake, Beaver Dam, and Scattertown.
After a day full of seasonal fun and outdoor excursions, you’ll likely have worked up quite an appetite. Luckily, Starkville offers a wide variety of eateries. Perhaps the most well-known is Restaurant Tyler, which serves Southern staples like fried green tomatoes, shrimp and grits, and fried catfish.
For a more casual, family-friendly meal, The Little Dooey is a beloved barbecue joint. The smoked pork plate with a side of hush puppies is a must-try — and don’t forget an extra side of barbecue sauce!
Here’s to an exciting fall!
This article is sponsored by Visit Greenwood, Visit Oxford, DeSoto County Tourism, Tupelo Convention and Visitors Bureau, Visit Cleveland, Explore Ridgeland, Visit Starkville, and Visit Mississippi.
