Tupelo, Mississippi Weekend Escapes: 10 Short Road Trips Nearby

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10 Easy Road Trips from Tupelo, Mississippi (That Are Worth the Drive!)

If you live in or around Tupelo, Mississippi and you’re itching to get out of town for a day, you’re in luck. You don’t have to drive all the way to Memphis or Birmingham to find fun things to do. Within about an hour or so, you’ve got small towns, state parks, and historic sites that are perfect for a short out-of-county road trip. In this guide, we’ll head out of Lee County into the nearby counties of Chickasaw, Itawamba, Monroe, Pontotoc, Prentiss, and Union. No need for a full weekend getaway—most of these spots work great as simple day trips from Tupelo.

1. Explore History at the Chickasaw County Courthouse Square (Houston, Chickasaw County)

About 35–40 miles southwest of Tupelo, you’ll find the small town of Houston in Chickasaw County. It’s a classic Mississippi courthouse town with a slower pace that feels like stepping back in time. Walk around the courthouse square, pop into a few local shops, and grab a bite at a mom-and-pop café. If you like small-town photography, this area is full of old brick buildings, faded signs, and tree-lined streets that look great in photos. For a simple day:
  • Stroll the historic downtown square
  • Check out any local murals or historic markers
  • Finish with ice cream or a slice of pie at a local diner
It’s not a “big” attraction, but that’s the charm. Sometimes the best road trips from Tupelo are the quiet ones.

2. Ride (or Walk) the Tanglefoot Trail (Houston & Pontotoc – Chickasaw, Pontotoc, and Union Counties)

The Tanglefoot Trail is one of the most popular outdoor things to do near Tupelo, and it stretches through several nearby counties, including Chickasaw, Pontotoc, and Union. This 43-mile rail trail runs along an old railroad corridor and is perfect if you enjoy:
  • Biking
  • Walking or jogging
  • Birdwatching and nature photography
You can hop on the trail at various trailheads outside Lee County, such as:
  • Houston (Chickasaw County)
  • Pontotoc (Pontotoc County)
  • New Albany (Union County)
Pack some water, light snacks, and maybe a small picnic. Even if you only walk a mile or two, the quiet, tree-lined path is a nice break from traffic and noise.

3. Go Boating and Fishing on the Tennessee-Tombigbee Waterway (Itawamba County)

Head east from Tupelo into Itawamba County, and you’ll eventually meet the Tennessee-Tombigbee Waterway, often just called the “Tenn-Tom.” This man-made waterway is a favorite spot for:
  • Fishing from the bank or by boat
  • Casual boating and cruising
  • Watching barges and river traffic go by
There are several public boat ramps and recreation areas on the Itawamba County side. Bring a cooler, a couple of folding chairs, and enjoy a slow afternoon by the water. It’s a great change of scenery without a long drive. If you have a small boat or kayak, this is one of the best short road trips from Tupelo for getting out on the water.

4. Visit the Small-Town Charm of Fulton (Itawamba County)

Fulton, the county seat of Itawamba County, is an easy drive east of Tupelo. While it’s not a big city, it has a nice mix of local flavor and everyday comforts. Things to do in and around Fulton:
  • Walk through its small downtown area and browse local stores
  • Grab coffee or lunch at a local café
  • Drive around Itawamba Community College’s campus
If you’re someone who enjoys simple drives, Fulton makes a relaxed half-day trip. Use it as a starting point, then head out on some of the county backroads to enjoy rolling fields, old churches, and those long Mississippi views.

5. Discover Aberdeen’s Antebellum Homes (Aberdeen, Monroe County)

If you’re into history, old houses, and Southern architecture, Aberdeen in Monroe County is a must. It’s one of Mississippi’s best-known towns for antebellum homes and historic buildings. As you drive through, you’ll see:
  • Large historic homes set back from the road
  • Old churches with tall steeples
  • Quiet streets lined with big trees
Many people enjoy a simple “home tour” from the car, just slowly cruising through town and taking in the architecture. You can also park downtown, walk around the historic district, and look for historical markers that tell the story of the area. If you enjoy day trips from Tupelo that feel a little “old South,” Aberdeen is a great choice.

6. Relax by the River in Amory (Monroe County)

Another Monroe County stop, Amory, sits along the Tombigbee River and has a long railroad history. It’s a good option if you’re looking for something low-key but still want a bit of variety. In Amory, you can:
  • Visit a riverside park for a picnic and river views
  • Walk or drive through the older parts of town
  • Check out local shops or grab a burger at a local joint
On a nice day, bring a blanket and a book, find a shady spot near the water, and just enjoy the breeze. This kind of short road trip from Tupelo is perfect when you don’t want anything too busy or crowded.

7. Browse Antique Shops in Pontotoc (Pontotoc County)

Drive west from Tupelo and you’ll reach Pontotoc, the seat of Pontotoc County. If you like to poke around in antique stores and thrift shops, this is an easy and fun outing. Things to do in Pontotoc:
  • Walk through the historic downtown area
  • Browse antiques, vintage items, and local crafts
  • Grab lunch at a local café or diner
If you’re already thinking about riding the Tanglefoot Trail, Pontotoc makes a natural stop. You can mix a little biking or walking with some shopping and a good meal, all within a short drive from Tupelo.

8. Enjoy Small-Town Life in Booneville (Prentiss County)

Heading north from Tupelo will take you into Prentiss County and the town of Booneville. It’s home to community life, local sports, and that classic small-town Mississippi feel. Ideas for a Booneville day trip:
  • Walk or drive through downtown and around the courthouse area
  • Check out local eateries (especially if you’re craving a plate lunch)
  • Drive through the community college area and surrounding neighborhoods
This is a good road trip from Tupelo when you just want to see a different town, eat somewhere new, and enjoy a change of scenery without a long haul.

9. Visit New Albany’s Historic Downtown (Union County)

New Albany in Union County has become a popular stop in North Mississippi for its walkable downtown and friendly atmosphere. It’s also one of the main hubs along the Tanglefoot Trail, so you can easily combine downtown exploring with a little time outdoors. What to do in New Albany:
  • Stroll through the revitalized historic downtown
  • Browse boutiques, antique stores, and local shops
  • Enjoy coffee, dessert, or a sit-down meal at a local restaurant
  • Walk a short stretch of the Tanglefoot Trail from the New Albany trailhead
If you like small towns that have put effort into their downtown areas, this is one of the best short day trips from Tupelo.

10. Take a Scenic Country Drive Through Union & Pontotoc Counties

Not every road trip needs a big “destination.” Sometimes the drive itself is the main event. If you have a free afternoon, try this:
  • Head west from Tupelo into Union County, aiming for New Albany or its nearby country roads
  • Loop down toward Pontotoc County on backroads instead of the main highway
  • Enjoy views of fields, farmhouses, and old country churches
Bring:
  • A camera or your phone for photos of the landscape
  • A simple picnic you can enjoy at a small roadside park or trailhead
These kinds of drives are great when you just need to clear your head. Roll down the windows, put on some music, and let the miles do their work.

Tips for Planning Short Road Trips from Tupelo, Mississippi

To make the most of these out-of-county day trips from Tupelo, keep a few basics in mind:
  • Check hours: Small-town shops and restaurants sometimes have limited hours, especially on Sundays.
  • Fill up first: Top off your gas tank before you leave Tupelo, just in case you end up on quieter backroads.
  • Bring cash: Some small businesses or events may be cash-only.
  • Pack a small bag: Include water, snacks, sunscreen, and maybe a light jacket, depending on the season.
Think of these trips as “mini vacations” close to home. You don’t have to book a hotel or spend a bunch of money to feel like you got away for a while.

Where Will You Go Next from Tupelo?

Living in or visiting Tupelo, MS doesn’t mean you’re stuck in one place. Within about an hour’s drive, you can:
  • Walk historic downtowns
  • Ride the Tanglefoot Trail
  • Relax by the river or waterway
  • Explore small-town shops and local restaurants
Now it’s your turn: Which of these short road trips from Tupelo would you try first? Do you prefer outdoor adventures, historic homes, or just a peaceful country drive?

Share Your Favorite North Mississippi Road Trips

I’d love to hear from you:
  • Have you visited any of these spots near Tupelo?
  • Do you have a favorite hidden gem in Chickasaw, Itawamba, Monroe, Pontotoc, Prentiss, or Union County?
Drop your tips and stories in the comments so other readers can discover new places too. If you found this guide helpful, please share it with friends and family who live in North Mississippi or are planning a visit. A simple share can help someone else discover their next favorite day trip from Tupelo.
Location: Georgetown, IN, USA

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