Grenada, Mississippi Weekend Escapes: 10 Easy Short Road Trips

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10 Easy Road Trips Near Grenada, Mississippi: Fun Day Trips Worth the Drive

If you live in or around Grenada, Mississippi and you’re itching to get out of town for a day, you’re in a great spot. Within about an hour’s drive, you can find small-town cafés, blues history, quiet lakes, old courthouses, and some very good country cooking. In this guide, we’ll look at 10 short out-of-county road trips from Grenada, all in neighboring counties like Calhoun, Carroll, Leflore, Montgomery, Tallahatchie, Webster, and Yalobusha. These are simple, low-stress adventures you can do in a morning or an afternoon.

1. Greenwood & the Blues Trail – Leflore County

Head about 35–45 minutes south to Greenwood in Leflore County, one of the most interesting small cities in the Mississippi Delta. You can:
  • Follow Mississippi Blues Trail markers around town and learn about Delta blues history.
  • Visit the grave sites of blues legend Robert Johnson (there are multiple claimed sites near Greenwood, which makes it an adventure in itself).
  • Walk around the historic downtown and the old Leflore County Courthouse.
  • Grab lunch at a local café or one of the classic Southern meat-and-three spots.
If you love music or just enjoy a relaxed Delta vibe, Greenwood makes a smooth, easy road trip from Grenada.

2. Coffee, Courthouse & Country Roads in Winona – Montgomery County

About 35 minutes west of Grenada, you’ll find Winona in Montgomery County. It’s small, friendly, and feels like classic Mississippi. Things to do:
  • Stroll around the Montgomery County Courthouse square and check out the old buildings.
  • Pop into a local coffee shop or diner for a burger, plate lunch, or slice of pie.
  • Take a slow drive along the back roads and enjoy the farmland and pine forests.
It’s not flashy, and that’s the point. This is a good trip when you just want a quiet change of scenery and a good meal.

3. Water Valley’s Artsy Main Street – Yalobusha County

Head about 45–50 minutes north to Water Valley in Yalobusha County. This little town has a surprising artsy streak and a cozy downtown. What to check out:
  • Walk Main Street and peek into art galleries, antique stores, and small shops.
  • Enjoy a laid-back meal at a local café or grab coffee and people-watch from the sidewalk.
  • Time your visit with one of Water Valley’s small-town festivals or events if you can.
If you like the idea of a small town with a creative feel, Water Valley is a fun and easy day trip from Grenada.

4. Historic Carrollton & North Carrollton – Carroll County

Just east of Grenada, in Carroll County, sit the twin towns of Carrollton and North Carrollton. Together, they make a nice half-day outing. You can:
  • Drive slowly through Carrollton’s historic district and admire the old homes and churches.
  • See the Carroll County Courthouse, one of the more picturesque courthouses in the region.
  • Enjoy a meal at a local spot, then ride across to North Carrollton for a quick look around.
This is a great Sunday-drive kind of trip—simple, relaxed, and full of old Southern charm.

5. Calhoun City & Pittsboro: Classic Small-Town Mississippi – Calhoun County

To the northeast, Calhoun County offers small-town life the way many people picture it—quiet, friendly, and unhurried. Two stops to pair together:
  • Calhoun City – Walk or drive through town, find a local café, and chat with the locals.
  • Pittsboro – Home to the Calhoun County Courthouse and a peaceful courthouse square.
This is a good trip when you want to slow down. Think front porches, courthouse lawns, and simple country roads.

6. Charleston & the Tallahatchie River – Tallahatchie County

About an hour northwest, Charleston in Tallahatchie County sits near the Tallahatchie River and has deep roots in Delta history. Things to do on this road trip:
  • Walk around downtown Charleston and see the old storefronts and the county courthouse area.
  • Drive out along the Tallahatchie River and enjoy the Delta landscape.
  • Stop at a local spot for classic Southern comfort food.
It’s a good outing for travelers who enjoy history, old towns, and wide-open skies.

7. Eupora’s Quiet Charm – Webster County

To the northeast in Webster County, about 45–55 minutes from Grenada, you’ll find Eupora, another quiet town that’s perfect for a low-key day. On your visit:
  • Take a spin through downtown Eupora and check out the small shops and old buildings.
  • Grab coffee or lunch at a local restaurant and soak in the small-town feel.
  • Ride the back roads of Webster County and enjoy the rolling hills and farmland.
If you like peaceful places without crowds, Eupora makes a relaxing road trip from Grenada.

8. Tillatoba & the Rural Back Roads – Yalobusha County

For a quick country escape, head to Tillatoba in southern Yalobusha County. It’s a tiny community, but sometimes that’s exactly what you need. Ideas for this outing:
  • Slowly cruise the back roads around Tillatoba and enjoy the fields, woods, and rural scenery.
  • Pack a simple car picnic—sandwiches, chips, a cooler—and find a safe pull-off or quiet spot to eat.
  • Pair this with a stop in another Yalobusha town to make a full day.
This is less about attractions and more about getting away from noise and enjoying a peaceful drive.

9. Duck Hill & Rural Montgomery County – Montgomery County

Just west of Grenada in Montgomery County, the small community of Duck Hill sits off Highway 51 and I‑55. What to do:
  • Take a slow drive through Duck Hill and nearby country roads, noticing old homes, churches, and fields.
  • Combine this stop with a visit to Winona (also in Montgomery County) for lunch or coffee.
  • Use the trip as an excuse to explore a few scenic side roads you’ve never driven before.
Sometimes the best short road trips are just you, the highway, and a tank of gas.

10. Duck Hunting, Fishing & Delta Scenery – Around Leflore & Tallahatchie Counties

If you enjoy the outdoors, the Delta regions of Leflore and Tallahatchie Counties offer plenty of chances for:
  • Duck hunting in season (through private guides or leases).
  • Fishing in local bayous, rivers, or oxbow lakes.
  • Sunset drives along the Delta back roads, with flat fields stretching out in every direction.
Even if you don’t hunt or fish, just driving these roads near sunset can feel like a mini-vacation—huge skies, long straight roads, and that quiet Delta air.

Tips for Planning Your Grenada-Area Day Trips

To make these short road trips from Grenada more fun:
  • Check opening hours: Small-town restaurants and shops may close early or shut down on Sundays.
  • Fill up with gas in Grenada: Some rural areas don’t have many stations.
  • Bring cash: A few older spots may not take cards.
  • Keep it loose: The best part of a day trip is the freedom to pull over when something looks interesting.
If you’re traveling with kids, turn it into a game—see how many courthouses, old churches, or cotton fields you can spot in one day.

Share Your Favorite Road Trips Near Grenada

Have you taken a fun day trip from Grenada, Mississippi into Calhoun, Carroll, Leflore, Montgomery, Tallahatchie, Webster, or Yalobusha County? Did you find a great café, a quiet fishing hole, or a pretty back road? Drop a comment below and share your favorite spots, tips, or stories. Your ideas might help someone else plan their next weekend adventure. And if you found this guide helpful, please share it with friends and family who live near Grenada or love exploring North Mississippi. A simple share can be the start of someone’s next great little road trip.
Location: Georgetown, IN, USA

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