Greenwood, Mississippi (Leflore County) 10 Best Short Road Trips

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10 Easy Road Trips From Greenwood, Mississippi (Leflore County) You’ll Love

If you’re in Greenwood, Mississippi and itching to get out of town for a day, you’re in a perfect spot. Within about an hour’s drive, you can reach lakes, historic downtowns, quiet country roads, and classic Southern food that will make you want to loosen your belt a notch. This guide focuses on short out-of-county road trips from Greenwood, heading into these nearby Mississippi counties:
  • Carroll County
  • Grenada County
  • Holmes County
  • Humphreys County
  • Sunflower County
  • Tallahatchie County
No need for a full tank and a suitcase—most of these trips are well under an hour away. Just grab your keys, a cooler, and maybe a friend, and go.

1. Grenada Lake & Hugh White State Park (Grenada County)

If you’re craving trees, water, and wide-open skies, head about 35–45 minutes northeast to Grenada Lake and Hugh White State Park. Here you can:
  • Swim at the lake’s public beach areas
  • Rent a boat or bring your own to fish for crappie and bass
  • Walk or bike easy lakeside trails
  • Spread out a picnic under tall pines
On a hot Mississippi afternoon, standing on the shore with a breeze coming off the water feels like someone turned down the world’s thermostat. It’s an easy, classic day trip from Greenwood if you want nature without roughing it too much.

2. Historic Downtown Grenada (Grenada County)

While you’re in Grenada, leave a little time for downtown Grenada. It’s one of those small Mississippi towns where the courthouse square still feels like the center of everything. What to do:
  • Walk the square and check out the historic buildings
  • Browse local shops for gifts or antiques
  • Grab lunch at a small-town café or diner
  • Snap a few photos of the courthouse and old storefronts
If you enjoy the quieter side of travel—just walking, looking, and taking it all in—this is an easy way to turn your lake day into a full road-trip experience.

3. Carrollton’s Historic Square (Carroll County)

About 30–40 minutes east of Greenwood, you’ll find Carrollton, a tiny town with a surprisingly charming historic district. The heart of the town is its old-fashioned square. Imagine classic Southern buildings, shady trees, and a pace of life that feels about 30 years slower—in a good way. Things to enjoy:
  • Stroll the historic streets and admire antebellum homes
  • Visit local churches and old buildings (some date back to the 1800s)
  • Chat with locals—you’ll probably get a story or two
  • Check for seasonal events and festivals on the square
If you like taking slow drives, getting a little bit lost on country roads, and stumbling onto history, Carrollton is a great short road trip from Greenwood.

4. Vaiden & Rural Carroll County Backroads (Carroll County)

For a different kind of outing, drive a bit farther along Highway 35 toward Vaiden. This isn’t a big tourist town—it’s more of a peaceful, everyday Mississippi community. What makes it worth the drive?
  • Scenic two-lane roads with rolling hills and farmland
  • Simple small-town food stops where you can grab a burger or a plate lunch
  • Old churches and cemeteries that tell stories of the area’s past
If you’ve ever just wanted to roll the windows down, turn on some music, and drive with no real schedule, this part of Carroll County is perfect. It’s about the feel of the day, not a checklist of attractions.

5. Tchula & Holmes County Delta Views (Holmes County)

Head southeast from Greenwood and you’ll reach Tchula and the surrounding areas of Holmes County. This is deep Delta country—flat fields, open skies, and long stretches of road. You can:
  • Take a leisurely drive along farm roads and levees
  • Stop by small convenience stores and local joints for snacks
  • Look for birds and wildlife near bayous, creeks, and oxbow lakes
This is a good trip if you enjoy photography or just want a reminder of how quiet the world can be once you leave town. The sunsets here can be stunning—bring your camera if that’s your thing.

6. Lexington’s Courthouse & Town Square (Holmes County)

About an hour from Greenwood, Lexington offers another classic courthouse-town-square combo, with its own personality and history. In Lexington, you can:
  • Walk around the historic Holmes County Courthouse
  • Explore shops and small businesses around the square
  • Hit a local café for coffee, tea, or a quick meal
If you like to pair your drives with a little bit of history and a lot of people-watching, Lexington makes for a relaxed day trip from Greenwood.

7. Belzoni: Catfish Capital of the World (Humphreys County)

West of Greenwood, you’ll find Belzoni in Humphreys County, known far and wide as the “Catfish Capital of the World.” If you love Southern food—and especially fried catfish—this one is a must. What to look for:
  • Local restaurants serving catfish and Delta-style sides
  • Catfish-themed artwork and displays around town
  • Flood-control levees and Delta scenery just outside the city
Belzoni is one of those places where you can build an entire day trip around a meal. Drive in, explore a bit, eat very well, then take the long way home through the countryside.

8. Indianola & the Blues Heritage (Sunflower County)

Just a short drive west from Greenwood is Indianola in Sunflower County, a small town with a big connection to the Mississippi Delta blues. Things to do in Indianola:
  • Walk along downtown streets and check out local murals and markers
  • Pop into small shops and cafés for snacks or coffee
  • Drive quiet roads around town for more Delta scenery
If you’re a music fan, this is a great area to soak in the atmosphere that shaped so much of American music. Even a quick afternoon visit can feel special.

9. Drew & Sunflower County Backroads (Sunflower County)

For a laid-back ride with a true Delta feel, head toward Drew and explore more of Sunflower County. You won’t find big tourist attractions here—but that’s part of the charm. On this drive you can:
  • See wide fields of cotton, soybeans, and other crops
  • Cross small bridges over bayous and drainage canals
  • Stop for photos whenever something catches your eye
If you’ve ever wondered what “Delta flat” really means, this little road trip from Greenwood will show you. It’s like driving across an ocean of land.

10. Sumner & the Tallahatchie Courthouse (Tallahatchie County)

Northeast of Greenwood, in Tallahatchie County, you’ll find the town of Sumner, known for its historic courthouse and its place in civil rights history. On a visit here, you can:
  • View the exterior of the historic courthouse
  • Walk the quiet streets and see older homes and buildings
  • Reflect on the area’s complex and important past
This is a quieter, more thoughtful kind of road trip, but it adds depth to your experience of the Mississippi Delta. It’s a reminder that these landscapes hold powerful stories.

Bonus: Charleston & the Tallahatchie River (Tallahatchie County)

If you want to keep going in Tallahatchie County, continue on to Charleston. It’s another small Delta town with tree-lined streets and nearby river country. Ideas for your visit:
  • Drive near the Tallahatchie River and look for fishing spots
  • Check out older neighborhoods and downtown streets
  • Take the back roads home for new views of the Delta
This is the kind of trip where you might discover a favorite little store or view you’ll want to come back to again and again.

Tips for Planning Your Greenwood Day Trips

To make these short road trips from Greenwood, MS more enjoyable, keep a few simple tips in mind:
  • Fuel up early: Some rural stretches don’t have many gas stations.
  • Bring water and snacks: Handy if you get caught up exploring.
  • Check hours: Small-town shops and restaurants may close earlier than you expect.
  • Take the back roads: When it’s safe and daylight, try a different route home.
  • Pack a camera or use your phone: The Delta light can be beautiful, especially near sunset.
One of the best parts of living in or visiting Greenwood, Mississippi is how quickly you can leave town and be surrounded by water, woods, or endless fields. You don’t need a plane ticket—just a free afternoon.

Share Your Favorite Greenwood Road Trips

Have you taken a day trip from Greenwood that you loved—maybe a hidden fishing hole, a local café, or a scenic stretch of highway in one of these nearby counties?
  • Which spot from this list are you most excited to visit?
  • Do you have a favorite catfish place, back road, or small town we should highlight next time?
Drop your thoughts in the comments and tell us about your own routes and must-see stops. If you found this guide helpful, please share it with friends and family who are looking for easy, fun things to do near Greenwood, Mississippi. Your shares and comments help keep this kind of local travel guide going—and might inspire someone’s next Sunday drive.
Location: Georgetown, IN, USA

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