Mississippi’s longest rail-trail, the Tanglefoot Trail winds through some lovely little towns, including Pontotoc. Few people have heard of the tiny town; however, if you’re travelling along the trail, you should definitely know about Pontotoc. Not only does it mark the trail’s halfway point, but it’s brimming with small town charm, making it a great detour.
Following the path of a former rail line, the Tanglefoot Trail spans 43.6 miles through the foothills of the Appalachians.
Larry Jarrett/All Trails A top-rated trail, it was inducted into the Rail-Trail Hall of Fame in 2019.
The trail begins in Houston, Mississippi and ends in New Albany, Mississippi, passing through several charming towns, including Pontotoc.
Tanya Thornberry/All Trails
Located about 25 miles into the journey, Pontotoc is roughly the trail’s halfway point and the perfect detour.
Pontotoc County Chamber Main Street/Facebook
Incorporated in 1836, the 6,000-person town is steeped in history, which visitors can learn all about at Town Square Post Office and Museum.
mississippihills.org
The museum’s vast collection includes antique items and artifacts relating to the area’s first residents as well as a large collection of historical exhibits, documents, books, and memorabilia.
MS Hills National Heritage Area/Facebook
Once you learn all about the Pontotoc of yesteryear, spend some time learning about the Pontotoc of today by exploring the boutiques, gift shops, and antique stores that fill downtown.
tanglefoottrail.com
The downtown also plays host to some great events since Pontotoc is an official Main Street Community. Beloved events, like the Bodock Festival and Christmas Parade, truly capture Pontotoc’s small town charm.
Bodock Festival/Facebook
The charm doesn’t end there, though. Not only does Pontotoc have a seasonal farmers market, but it’s home to an orchard!
Cherry Creek Orchards/Facebook
Finding a good meal in Pontotoc is as easy as finding something to do. From BBQ to Mexican, the town boasts an appetizing array of eateries.
Southern Foodways Alliance/Flickr
With so much to offer, Pontotoc isn’t just the Tanglefoot Trail’s halfway point. It’s a great day trip destination all its own!
tanglefoottrail.com
Larry Jarrett/All Trails
A top-rated trail, it was inducted into the Rail-Trail Hall of Fame in 2019.
Tanya Thornberry/All Trails
Pontotoc County Chamber Main Street/Facebook
mississippihills.org
MS Hills National Heritage Area/Facebook
tanglefoottrail.com
Bodock Festival/Facebook
Cherry Creek Orchards/Facebook
Southern Foodways Alliance/Flickr
To learn more about Pontotoc as well as the other sites along Mississippi’s longest rail-trail, visit the Tanglefoot Trail website.
Looking for another must-visit town on the Tanglefoot Trail? Check out New Albany, which has been named one of the best small towns in the South.
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Address: Pontotoc, MS 38863, USA
