Cleveland, Mississippi (Bolivar County): 10 Best Things To Do Nearby

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10 Fun Things To Do In And Around Cleveland, Mississippi (Bolivar County)

If you’re road-tripping through the Mississippi Delta or planning a weekend getaway, Cleveland, Mississippi is a small town that delivers big on music, history, and Southern charm. Tucked in Bolivar County, it’s right in the heart of the Delta, about halfway between Memphis and Jackson, and it makes a great base to explore the region. Below are 10 things to do in and near Cleveland, MS that blend local flavor, culture, and a whole lot of Delta soul.

1. Explore the GRAMMY Museum Mississippi

You might not expect to find a world-class music museum in a small Mississippi town, but Cleveland pulls it off. The GRAMMY Museum Mississippi is the first GRAMMY Museum built outside of Los Angeles. Inside, you’ll find:
  • Interactive exhibits where you can try mixing your own track
  • Hands-on stations that let you play with instruments and recording tech
  • Rotating displays highlighting music legends and rising stars
It’s a great stop whether you’re a hardcore music nerd or you just like to sing along in the car. Plan to spend at least 1–2 hours here. Families with kids will especially like all the push-button displays and touch screens.

2. Walk Through Delta State University’s Beautiful Campus

Right in town, Delta State University gives Cleveland a lively college-town feel. The campus is compact, walkable, and full of trees and green spaces. Things to do on or around campus:
  • Stroll the walking paths and enjoy the shade on a hot afternoon
  • Catch a college baseball, football, or basketball game if you’re in town during the season
  • Look for campus events like concerts, lectures, or art shows that are open to the public
It’s an easy way to stretch your legs, especially if you’ve been driving along Highway 61 for a while.

3. Dive Into Delta Blues History at the Dockery Farms Historic Site

A short drive from downtown Cleveland, Dockery Farms is often called the “Birthplace of the Blues.” This former cotton plantation is where musicians like Charley Patton played and shaped the Delta blues sound that later influenced rock and roll. At Dockery Farms you can:
  • Walk around historic buildings and markers
  • Read signs that explain how the blues grew out of Delta life
  • Take in the quiet fields and imagine the music that once echoed here
It’s a simple site—no flashy attractions—but it’s powerful. If you love music history, this is almost a bucket-list stop.

4. Discover Local Art at the Bologna Performing Arts Center & Galleries

On the Delta State campus, the Bologna Performing Arts Center (locals say “Bo-LO-nya,” like the lunch meat) brings big performances to a small town. Depending on when you visit, you might find:
  • Touring Broadway-style shows
  • Concerts from well-known performers and local musicians
  • Children’s theater and family-friendly events
  • Art exhibits in the lobby and gallery spaces
If you like to plan ahead, check their schedule before your trip. Catching a show here is a fun way to wrap up a day of exploring Cleveland.

5. Shop and Stroll in Downtown Cleveland

Looking for a classic small-town Main Street vibe? Downtown Cleveland delivers with brick storefronts, local businesses, and a relaxed pace. As you wander around:
  • Browse boutiques selling clothing, gifts, and Delta-themed souvenirs
  • Pop into local bookstores and specialty shops
  • Grab coffee, ice cream, or a slice of pie at a café
If you time it right, you might catch a festival, live music event, or holiday celebration on the downtown streets. The town really comes alive during special events, and locals are usually happy to chat.

6. Enjoy Classic Southern Food at Local Restaurants

You can’t visit Cleveland, Mississippi without digging into some Southern comfort food. This is Delta country, after all. In and around town, look for:
  • Catfish plates with hush puppies and coleslaw
  • Barbecue ribs and pulled pork sandwiches
  • Fried chicken, greens, and cornbread
  • Homemade desserts like pecan pie or cobbler
Ask locals, “Where do you eat on a Friday night?” You’ll usually get a straight answer and maybe even a detailed rundown of what to order. Don’t be shy—small-town restaurant recommendations are often the highlight of a trip.

7. Get Outside at Local Parks and Trails

Cleveland may be flat Delta land, but it still offers some nice spots to get outdoors, especially if you want a break from the car. Around town you can:
  • Walk or jog on community walking trails
  • Relax in neighborhood parks with playgrounds and picnic tables
  • Let kids burn off energy while you enjoy some shade
If you’re traveling with a dog, these little parks and paths are perfect quick stops. Bring a simple picnic and enjoy a slow Southern afternoon.

8. Take a Day Trip to Nearby Delta Towns

Cleveland makes a great hub for exploring other Mississippi Delta towns in Bolivar County and nearby areas. Within an easy drive, you can:
  • Head north toward Clarksdale for more blues clubs and museums
  • Explore nearby small towns with historic downtowns and roadside diners
  • Follow Highway 61 (the famous “Blues Highway”) and stop wherever catches your eye
The fun of the Delta is often in the wandering. Roll down the windows, put on some blues, and see what you find.

9. Experience Local Festivals and Events

Cleveland and Bolivar County host several seasonal events that show off local music, food, and community pride. Dates can change year to year, but it’s worth checking what’s happening when you plan your visit. Depending on the season, you might catch:
  • Music festivals featuring blues, country, and rock
  • Food events with barbecue, tamales, and other Delta favorites
  • Holiday parades and downtown celebrations
If you enjoy small-town festivals, these gatherings are a great way to meet locals, hear live music, and sample regional dishes you might not find anywhere else.

10. Drive the Scenic Roads of the Mississippi Delta

Sometimes the best thing to do near Cleveland is simply…drive. The Delta’s wide-open fields, old barns, and straight-as-an-arrow roads have a mood all their own. It’s quiet, a little haunting, and incredibly beautiful at sunset. To make the most of it:
  • Set aside a couple of hours just to explore back roads around Cleveland and Bolivar County
  • Stop for photos at historic markers, churches, and cotton fields
  • Play a blues playlist and let the landscape match the soundtrack
It’s not a thrill-ride type of attraction—it’s more like stepping into a living postcard of the American South.

Planning Your Trip to Cleveland, Mississippi

Here are a few quick tips to make your visit smoother:
  • Best time to visit: Spring and fall, when temperatures are milder and festivals are more common.
  • How long to stay: A weekend is perfect to see the main sights, but you could easily spend longer exploring the wider Delta.
  • Getting around: You’ll want a car—this is rural Mississippi and attractions are spread out.
If you love music history, Southern food, and laid-back small towns, Cleveland, MS is a great stop to add to your Mississippi Delta itinerary.

What Would You Do in Cleveland, MS?

Have you visited Cleveland, Mississippi or anywhere in Bolivar County?
  • What was your favorite thing to do?
  • Did you discover any hidden-gem restaurants or shops?
  • Are there other must-see spots you’d add to this list?
Share your thoughts in the comments—your tips can help other travelers planning their own Delta adventure. If you found this guide helpful, please share it with friends, post it on social media, or send it to someone planning a road trip through Mississippi. The more we share, the more people get to experience this unique corner of the South.
Location: Georgetown, IN, USA

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