Cleveland, Mississippi (Bolivar County) 10 Short Road Trips Nearby

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10 Easy Road Trips From Cleveland, Mississippi: Fun Things To Do Just Outside Bolivar County

Cleveland, Mississippi might be your home base, but sometimes you just want to hop in the car, roll the windows down, and see what’s waiting a short drive away. If you’re looking for short road trips near Cleveland, MS that take you out of Bolivar County, you’re in luck. The surrounding counties in Mississippi and Arkansas are packed with Delta history, blues music, river views, and good down‑home food. Below are 10 easy out‑of‑county road trips from Cleveland, focusing on:
  • Coahoma County, MS
  • Sunflower County, MS
  • Washington County, MS
  • Phillips County, AR
  • Desha County, AR
  • Chicot County, AR
All of these are doable as day trips or relaxed weekend getaways.

1. Clarksdale, MS – Blues, Juke Joints, and the “Crossroads” (Coahoma County)

If you love live music or Delta history, Clarksdale should be near the top of your list. It’s only about an hour from Cleveland, but it feels like stepping into a living blues museum. Things to do in Clarksdale:
  • Visit the Delta Blues Museum and learn about legends like Muddy Waters and B.B. King.
  • Stop by the famous “Crossroads” where Highways 61 and 49 meet, and snap a photo under the iconic guitar sign.
  • Catch live music at local spots and juke joints most nights of the week.
  • Wander Downtown Clarksdale’s shops and art galleries.
On my last visit, I walked into a small club on a random Tuesday night and heard one of the best guitar players I’ve ever seen. No big stage, just a man, a guitar, and a crowd that didn’t want the night to end. If you’re curious about the Mississippi Delta blues trail, this is a perfect, easy road trip from Cleveland.

2. Helena, AR – River Town Vibes and Blues Heritage (Phillips County)

Just across the Mississippi River, Helena, Arkansas, in Phillips County, is another classic Delta town with a rich music story. Highlights in and around Helena:
  • Walk along the Mississippi River levee and enjoy the wide‑open views.
  • Learn about local history at small museums and historic markers around town.
  • Check out sites connected to the King Biscuit Time radio show, a major piece of blues history.
  • Explore the historic downtown area, with its older buildings and river-town feel.
Helena has a slightly weathered charm. It’s the kind of place where a slow walk down a side street can turn into a history lesson if you talk to the right person.

3. Tunica River Area – River Views and Casinos (Coahoma/Tunica Region)

While Tunica itself is in another county, you can easily access the lower Mississippi River region from the Coahoma County side, not far from Clarksdale. Things to do near the river:
  • Enjoy scenic drives along or near Highway 61 toward the river.
  • Stop at riverside overlooks or pull‑offs to watch barges and boats go by.
  • If you’re into gaming, continue on toward the Tunica casino area for an evening.
This makes a nice add‑on to a Clarksdale trip. You could explore blues by day and then unwind by the river in the late afternoon or evening.

4. Greenville, MS – Riverfront, Museums, and Classic Delta Food (Washington County)

Head south from Cleveland and you’ll reach Greenville in Washington County, another strong choice for a short road trip in the Mississippi Delta. What to do in Greenville:
  • Walk or drive near the Mississippi River and check out levee parks and overlooks.
  • Visit local museums and cultural centers that share the story of the Delta’s people and past.
  • Try classic Delta cuisine at local restaurants—think catfish, barbecue, and hearty Southern sides.
  • Explore historic neighborhoods and older church buildings.
If you like small‑town drives, you’ll enjoy wandering Greenville’s side streets. It’s the kind of place where you can grab a plate lunch and just watch local life move at a slower pace.

5. Leland, MS – Birthplace of Kermit and Delta Backroads (Washington County)

A little closer than Greenville, Leland is another Washington County stop that’s easy to pair with other towns. Ideas for your Leland visit:
  • Stroll through downtown and explore local shops and old storefronts.
  • Drive the surrounding Delta backroads for scenic farm and field views.
  • Enjoy small cafes or diners that serve up simple, satisfying meals.
Leland is a good stop if you’re piecing together a loop that might include Greenville, Indianola, and other nearby towns.

6. Indianola, MS – Blues Heritage and Delta Town Charm (Sunflower County)

Just a short drive from Cleveland, Indianola in Sunflower County is another great destination for Delta history lovers and relaxed travelers. What makes Indianola worth the trip:
  • Explore downtown streets lined with older buildings and local businesses.
  • Seek out historic markers and sites tied to Delta music and culture.
  • Enjoy a quiet lunch in town and then go for a slow drive through surrounding farm country.
The pace here is unhurried. It’s the kind of place where you can spend an afternoon just wandering, talking to shop owners, and soaking up the local vibe.

7. Ruleville & Drew, MS – Small‑Town Delta Drives (Sunflower County)

If you enjoy scenic drives and tiny town exploring, head over to Ruleville and Drew in Sunflower County. How to enjoy this area:
  • Drive through the towns and check out old homes, churches, and storefronts.
  • Take the backroads between towns for miles of Delta farmland views.
  • Stop at local gas stations or small stores—those quick chats often lead to great local tips.
This is the kind of road trip where the journey itself is the highlight. Roll the windows down, turn up some blues or country music, and just see where the road leads.

8. Lake Village, AR – Lake Chicot and Waterfront Relaxation (Chicot County)

Cross the Mississippi River into Arkansas and you’ll find Lake Village in Chicot County, right along Lake Chicot, one of the largest oxbow lakes in North America. Things to do around Lake Village:
  • Walk or drive along the shore of Lake Chicot and enjoy the water views.
  • Pack a picnic and relax near the lake under shady trees.
  • Look for spots to fish, watch birds, or simply unwind by the water.
If Cleveland feels busy and you’re craving a quiet spot, Lake Village delivers that laid‑back, peaceful lake‑town feel.

9. Arkansas City, AR – River History and Delta Scenery (Desha County)

Tucked away in Desha County, Arkansas City gives you a taste of an old river town that has seen the ups and downs of life along the Mississippi. What to do in and around Arkansas City:
  • Drive near the levees and river access points to get close to the Mississippi.
  • Explore town streets and hunt for historic buildings and markers.
  • Combine this stop with Lake Village or Greenville for a full river‑themed day trip.
It’s not a flashy place, but if you enjoy quiet roads and history, it’s worth the drive from Cleveland.

10. McGehee & Surrounding Delta Farmland (Desha County, AR)

Another Desha County option is McGehee and the nearby farm country. This is a good pick if you like simple, scenic drives and small‑town stops. How to enjoy a McGehee‑area road trip:
  • Explore the town’s main streets, old buildings, and local businesses.
  • Drive out into the surrounding countryside for wide, open Delta views.
  • Stop for a casual meal or snack at a local diner or café.
This trip is less about big attractions and more about the feeling of being out on the open road, away from your usual routine.

Tips for Planning Your Out‑of‑County Road Trips From Cleveland, MS

To make the most of these day trips from Cleveland, Mississippi:
  • Check driving times: Most of these spots are roughly 30 minutes to 2 hours from Cleveland. Perfect for a day trip.
  • Fill up the tank: In the Delta, gas stations can be spread out once you leave town.
  • Bring cash: Some small, older places may not take cards.
  • Be flexible: The best moments are often unplanned—an unexpected café, a roadside fruit stand, or a scenic side road.
If you’re ever unsure where to go next, a simple question at a gas station—“What’s good to see around here?”—can lead to surprising discoveries.

Share Your Delta Adventures

Out‑of‑county road trips from Cleveland, MS are all about:
  • Short, easy drives
  • Affordable fun
  • Real Delta culture, history, and scenery
Have you taken any of these routes from Cleveland—maybe to Clarksdale, Greenville, Indianola, Lake Village, or Helena? Tell us about it!
  • Which small town surprised you the most?
  • Did you find a favorite café, river lookout, or blues spot?
Drop your stories, tips, and favorite stops in the comments, and feel free to share this post with friends and family who are looking for easy road trips near Cleveland, Mississippi. Your experiences can help someone else plan their next Delta getaway.
Location: Georgetown, IN, USA

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