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Our practical guide to biking the Tanglefoot Trail, Natchez Trace, and Tupelo will get you out and riding some of the most beautiful areas in Northern Mississippi. Starting with the 44-mile Rail-to-Trail Hall of Fame Tanglefoot Trail, we’ll take you on a whistlestop ride along an old rail corridor in pastoral farmlands. Then, we’ll show you the absolute best 10-miles of cycling on the scenic Natchez Trace Parkway. Finally, we’ll take you into the charming town of Tupelo for some great food, good sleep, and a ride along the self-guided Elvis Trail.

We’ll wrap up the guide with suggestions about the best times to ride and ways to turn these fun outings into a full-on cycling weekend. Saddle up and come ride with us as we explore the Tanglefoot Trace and beyond.

Tanglefoot Trail Section
Tanglefoot Trailhead bike art

Interactive Map to the Tanglefoot Trail

Below are two maps of the Tanglefoot Trail. The embedded Google Map has all the rest stops along the trail, along with the best and most accessible restaurants and stores along the way. There are also a couple of B&Bs along the Tanglefoot Trail included. These highlights are grouped together into each trail town.

The MapMyRide Route is drawn from New Albany heading south. It has a rolling elevation profile which shows that the trail’s highpoint is in Pontotoc. Both maps can be downloaded to your smartphone and used for navigation. If you don’t see the maps below, be sure to refresh your browser 😉.

Tanglefoot Trail Description

The Tanglefoot Trail and Longleaf Trace are in a bit of a competition to be Mississippi’s longest rail-to-trail path. Right now, with the extension into downtown Hattiesburg, the Longleaf Trace is clocking in at 45 miles, which is just a smidge longer than the Tanglefoot, which is listed at 43.6 miles. There is a little extension past the Houston Trailhead, with plans to build more so the Tanglefoot might once again claim the longest trail title soon.

The route from New Albany to Houston has been traveled for centuries. First, as a Native American trade route, then as a railway on the Gulf and Ship Island Railroad in 1871. Literary buffs will recognize the name of its builder, Col. William Clark Falkner. He was an author in his own right but more famously known as the grandfather of the Nobel Prize-winning author, William Cuthbert Faulkner. In 2013, the rail corridor found new life as a paved multi-use trail – The Tanglefoot Trail.

The Tanglefoot is 43.6 miles long, with 770 of elevation gain along the way, and passes through the towns of New Albany, Ingomar, Ecru, Pontotoc, Algoma, New Houlka, and Houston. Except for New Albany, each town has a trailhead or Whistlestop with parking, water, and restrooms. There are restaurants or convenience stores in each of these towns, except for Ingomar. In the next section, we’ll discuss the best way to plan your ride along the Tanglefoot Trail.

Tanglefoot Gateway in New Albany
Ecru Whistlestop
Tanglefoot Trail Gateway in Houston
Pontotoc Gateway

Ride Plans for the Tanglefoot Trail

There are many ways to slice and dice the Tanglefoot into smaller rides, but we’ll only focus on two – a 37-mile out-and-back from New Albany to Pontotoc or an 87.2-mile out-and-back starting from Houston and covering the entire trail.

If you’re only going to ride half the Tanglefoot, there are several reasons to start in New Albany. First off, New Albany is right off of I-22, which makes it the logistically easiest trailhead to reach. Also, it has you biking uphill to Pontotoc initially, so you know your car is waiting at the bottom of the gradual but noticeable hill.

The New Albany Trailhead is a park, but it doesn’t have parking. However, you can park further up Railroad Ave or at the County Library. There are plenty of yummy restaurants in New Albany and even a couple in Pontotoc, so you’ll have your choice of SAG stops. However, the map can be misleading in Pontotoc. We’re not fans of crossing or biking on Hwy 15, so that rules out some options. Also, there are several bridges on the trail in Pontotoc, so you might not be able to reach every street the trail crosses. Your best bet is to head into historic downtown Pontotoc from the Pontotoc Gateway.

If you’re riding the entire trail, it’s a bit of a coin flip if you start from Houston or New Albany. There are more fun lodging options in Houston, and the food is better in New Albany. Given that, it makes sense to overnight in Houston and start early in the morning to get to New Albany. There, you can grab a bite before returning. However, if you’re staying in Tupelo and driving in, you’re better off starting in New Albany. Another option, which is what we did, is to start from New Albany and have one group ride the trail one-way from New Albany to Houston and have another group flip halfway at Pontotoc and bring the shuttle car down to Houston.

Tanglefoot Trail bridge and flowers
Tanglefoot Trail lake and woods

Interactive Maps for the Natchez Trace in Tupelo

Below are our interactive maps for the Natchez Trace in Tupelo. In the next section, you’ll hear more about The Trace, but everything is identified by mileposts (MP) for mapping sake. MP 0 is in Natchez MS, and MP 244 is in Nashville, TN. Our map runs 52 miles from MP 282 to MP 230. We identify access points and points of interest along the way.

The MapMyRide snippet runs from the Natchez Trace Visitor Center at MP 266 to the Twentymile Bottom overlook at MP 278.4. We chose this snippet because it’s a heavily forested region close to Tupelo, but don’t worry; we’ll cover ride details in a little bit. If you don’t see the maps below…you know what to do 😉.

Natchez Trace – Tupelo Description

The Natchez Trace Parkway is a 444-mile recreational road that travels through three states. It follows a thousand-year-old Indian trade route that turned into a significant military supply route for the Battle of New Orleans during the War of 1812. The entire parkway is designated as a bike route by the National Park Service.

There is no commercial traffic allowed on the Trace, and generally, traffic is light with two exceptions: Jackson and Tupelo. These are the two largest cities along the Trace and the only places where an Interstate Highway crosses the Trace. Jackson has the Chisha Foka Multi-Use Trail as an alternative for riders looking to beat traffic. Tupelo has no such amenities. However, the easy access provides opportunities for day rides in Tupelo, especially if you have a ride plan to help with traffic.

Drone shot of the Natchez Trace

Ride Plans for the Natchez Trace in Tupelo

We have set the stage already. There is a beautiful forested region of the Trace around the Visitor Center (MP 266), but you have to be prepared to share the road. The Park Service’s biking suggestions are a great place to start. If possible, it might be a good idea to avoid biking on the weekends, too, especially if you’re using this post as a guide for a bike getaway in Tupelo. You’ll have the lightest traffic during weekday mornings.

Another solid idea is to just take a little ride on the parkway from the Visitor Center (MP 266) to the Old Trace and Confederate Gravesites Pullout (MP 269.4). Sure, it’s only a 7-mile out-and-back, but this particular section of road has relatively wide shoulders and has minimal elevation change. You can get “some miles” on the Natchez Trace and still have time for other rides in the area.

Natchez Trace Visitor Center
Natchez Trace section
Natchez Trace sign

Interactive Maps for the Tupelo Self Guided Elvis Bike Tour

Just like before, this section has two parts: a Google Map insert and a MapMyRide insert. The Google Map has all the stops on the Self Guided Elvis bike tour, and the MapMyRide insert has elevation and distances. However, the town is relatively level, so you don’t have to worry about that.

Our suggestion is to load up the Google Map for navigation because it has the actual location of the historical markers, which are somewhat hard to read. However, worse comes to worst, it has the descriptions too. Also, it has some yummy places to stop and eat along the way.

Riding the Tupelo Self Guided Elvis Bike Tour

We started our ride from the Visitor Center / Holiday Inn and worked our way counter-clockwise to the Mayhorn Grocery (most Northerly point). During our ride, our only navigation snafu was turning onto Robins St from Jackson St. We were looking at the closest road signs, and Robins St turns to Highland Circle when it crosses Jackson St. We should have been looking for Highland Circle, and then made our left onto Robins.

A couple of critical points, many stores in downtown Tupelo close early on weekdays (~5:00), are only open Saturday morning, and are closed on Sundays. If you want to stop into Tupelo Hardware to stand where Elvis bought his first guitar or buy an Elvis-themed popsicle, be sure to check store hours and plan accordingly. Also, we didn’t ride under US 45. It’s a safe enough route traffic-wise, but there was too much road debris for our 25-mm tires. However, driving over to the Elvis Birthplace is absolutely worth it!

Tupelo Visitor Center and Elvis Sign
Downtown Tupelo / Hardware Store
Tupelo Elvis Homecoming Statue
Tupelo Guitar Trail

Best Time of Year for Biking Near Tupelo Ms

Tupelo is in the heart of the South, so your best bet is to ride in the spring or fall and start early in the morning if you’re riding in the summer. Wintertime high temperatures are in the low 60s, so it’s possible to ride then, but you might have a cold snap that alters your plans. Also, be careful of rain in the early spring. The wettest days of the year are centered around Valentine’s Day.

Funky house on the Tanglefoot Trail
Tanglefoot Trail section with a field of flowers

Wrapping Up This Practical Guide (aka How to Make These Rides Into a Bike Getaway)

There are many reasons to make an Elvis-themed weekend getaway to Tupelo, and it’s easy to turn that into a bike weekend. The first step is to show up early enough on Friday evening to enjoy downtown Tupelo, the only city in the Southern United States to be named an All-America City five times. Do the western half of the Tupelo Self Guided Elvis Bike Tour, enjoy some great food, and get a room at the Holiday Inn (which is conveniently where our ride starts from ;-)). On Saturday, get out and ride as much of the Tanglefoot Trail as your legs can handle. For Sunday, ride the 7-mile out-and-back from the Natchez Trace Visitor Center first thing in the morning and visit the Elvis Presley Birthplace before you leave town.

You can also work Tupelo into a week-long bike riding extravaganza. Nearby rides include the 45-mile long Longleaf Trace in Hattiesburg and the 31-mile-long Tammany Trace on the north shore of Lake Ponchartrain. If you’re down at Lake Ponchartrain with bikes, you can also check out biking in New Orleans and riding the Louisiana portion of the Mississippi River Trail.

Whether you are riding through Elvis’ childhood or hammering out hundreds of miles on dedicated trails, Tupelo has a ride (or two or three 😉) for you!

Remember to ride safely and read our bike disclaimer before you go

Disclosure: A big thank you to My Tupelo for hosting us and setting up a fantastic itinerary! For more travel inspiration check out their Instagram, Facebook, and Twitter accounts.

As always, the views and opinions expressed are entirely our own, and we only recommend brands and destinations that we 100% stand behind.

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The Natchez Trace road and wildflowers
Tupelo Ms mural and bike trail
Tanglefoot Bike Trail

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