Looking for the best trails around Tupelo?

Explore the best rated trails in Tupelo, MS, whether you're looking for an easy walking trail or a bike trail like the Tupelo Veterans Park Trail and Oxford Depot Trail . With more than 5 trails covering 50 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Tanglefoot Trail

tanglefoot

August, 2024 by mlantrip55

Great trail to ride , started in New Albany by the library rode to Ecru 22 miles round trip ! The train station stops are very nice including Ingmor , cold water , clean restrooms, and an ice chest filled with candy bars Dorthy has the stop decorated with beautiful flowers and plants! Great job , if your a cyclist and traveling through Mississippi a must stop trail to ride !

Tanglefoot Trail

Tanglefoot April 2024

April, 2024 by coachtandem

The trail is completely paved and smoothed. We had a great time and did the entire 44 miles both ways. Here's the sad truth. It would earn 5 starts if it was in a different location.... Or make a connecting trail to Tupelo. This would allow a cyclists to hook up with the Natchez Trace Parkway and do a complete triangle. I would not recommend riding this in the summer as it goes through several low forested areas where bugs and humidity would be unbearable. We cycled this on a beautiful April weekend and we only saw maybe 6 other cyclists the entire time. This is not a cycling mecca and therefore the trail is not supported like it could/should be. A trailside lemonade stand would go under if it depended on trail users!
We would HIGHLY recommend staying at Daisy's on the Square in Houston and Eating their steak & baked potato!!
Pros: smooth, safe, You can't get lost!
Cons: Not enough trail users to support this hidden crown jewel. (small population base) Could use a shuttle service if you only want to go one way.
trailside depot restrooms aren't cleaned very often. Our Gold Standard is the Katy Trail depot Restrooms which are always clean!

Tanglefoot Trail

We rode from Pontotoc to the south end in Houston and back. It was a beautiful ride and paved all the way. The temp was 50 to 70 with little wind. It was very enjoyable. We did encounter a cottonmouth at about mile marker 13 so keep an eye out.

March, 2024 by jpotucek

We rode from Pontotoc to the south end in Houston and back. It was a beautiful ride and paved all the way. The temp was 50 to 70 with little wind. It was very enjoyable. We did encounter a cottonmouth at about mile marker 13 so keep an eye out.

Accordion

Tanglefoot Trail

Fun trail

October, 2023 by ltbike

The trail is really great. Very good surface and signage is good for trailheads. It is mostly in the woods and very shady. We were there in early October and had some very chilly, windy days. We encountered dogs running loose at a rural house near Houston—they chased some other bikers and we happened to be stopped so we threw rocks at them (the dogs) so they would go off the trail. Another dog was running loose with some walkers at New Houlka and was growling at us but according to the owner “won’t bite you!!” One loose dog encounter was between Potontoc and Algoma. They were all nothing we couldn’t handle—just something to be prepared for. Don’t let this stop you because this trail is great and some nice little towns along the way. We did encounter a number of other trail users off and on. We were camped at Potontoc. Be sure to eat at Seafood Junction at Algoma, MS

Tanglefoot Trail

2nd Trip Tanglefoot

September, 2023 by garybrogers

Well on September 15th we returned to Tanglefoot trail, this time we started out in Pontotoc and we rode our Catrike to New Albany, took about a 30 minute break, then headed back south on the trail, stop in Ecru an ate lunch at Zuby’s Cafe, Great Catfish!! Then we were headed to the Pontotoc/ Chickasaw county line, then turned around an headed back to Pontotoc. This is a Great Trail!!! Some of bridges are getting a little rough an will need some repairs in the near future, and there was a few rough spots in the trail south of Pontotoc, All restrooms were clean, most of the trail is patrolled by security during the daytime

Tanglefoot Trail

1st Rail to Trail ride

August, 2023 by garybrogers

We recently purchased two trikes, wife and I made our first adventure on Tanglefoot, rode from Houston to the county line just north of New Houlka, an back, about a 25 mile round trip. Was a Great experience, looking forward to more trips on Tanglefoot

Tanglefoot Trail

My grandson and I did the South 15 miles of this trail today. Highly recommend anybody. The wife and I did the middle part of this trail a couple weeks ago. Lots of food trucks in Pontotoc.

July, 2023 by dundeeyank

My grandson and I did the South 15 miles of this trail today. Highly recommend anybody. The wife and I did the middle part of this trail a couple weeks ago. Lots of food trucks in Pontotoc.

Tanglefoot Trail

The Tanglefoot Trail (T2) on 1 JUN 23

June, 2023 by 7s5a692x35

3 of us rode from New Albany to Houston and enjoyed the experience as the trail surface was smooth and there was a tree canopy for the majority of the trail. The bridge surfaces were not smooth due to the wooden planks being weathered and raised up. ~5 miles from Houston, there was a bridge that was resurfaced with concrete and chip-n-seal and was extremely rough.

There quite a few people on the trail especially near the populated areas but they were kind and moved to one side. In Houston, there is a restaurant called the Gathering and a very, nice lodging opportunity at the end of the trail named Trailhead bike and bed.

Go experience the Hall of Fame T2!

Tanglefoot Trail

Awesome Experience

March, 2023 by marcosalexandermendoza

I go biking with my 2 daughters on the trail, and we love it! We have probably biked the whole system.

Tanglefoot Trail

The Tanglefoot Trail, Aug. 6, 2022

December, 2022 by cwiokster

Did a recent [Aug. 6, 2022] 2nd ride on The Tanglefoot Trail, in NE Miss. Started in New Albany, MS, at the "Little Tallahatchie riverfront park" trail (1.4 mi) to start off Fri. PM before the main ride Sat. This is the 3rd RTC "Hall of Fame" trail in my 'Trail Collection'. More to come. This one is worth the trip.🚵¿¿¿ Despite the heat & cutting the ride short, I still managed 51.2 miles. In August, I'm good with that! My first ride on this trail, was on October 12, 2019, and I managed the full trail, (plus the ride from the hotel), for a total of 92.75 miles. Both rides started ( and finished) in New Albany. First ride I picnic lunched at the Houston Trailhead, 2nd ride, turned around south of Pontotoc, and lunched at the Gateway rest area there. Really appreciated the 'Whistle Stop' rest areas, as I am a "trail cruiser" and tend to take a few minutes off the bike along the way. The only surprise was how many of the frequent bridges were washboarded with 'cupped' planks! [took off a star for that] Quite "exciting"; the video cam mount didn't survive (cheap plastic), but I improvised with some string I carry for emergencies, and carried on. On the plus side, I loved the clearly visible mile markers, which help you keep up with progress on the trail. Quite a variety of scenery, from urban to wooded to farmlands, as you cross the 3 counties. All in all, an enjoyable ride. Will do this again.

Tanglefoot Trail

nice fall ride

October, 2022 by jgraves226

The trail is Awesome. It was a beautiful fall day. I plan on returning again. I live in Louisville Ky.

Tupelo Veterans Park Trail

Veterans Park + Surrounding Routes

May, 2022 by tjxqhkwhyj

Okay, so this trail is noted to be just shy of a mile, HOWEVER, it connects to a sidewalk on Veterans Blvd. that runs to Main St., all the way to downtown Tupelo, where you can easily run a few loops around local and historical sites, Fairpark, or the historic neighborhoods on either side of the commercial district. If you want more earth and foliage, you can cross Veterans at Elvis Presley Dr. or by the fire station in front of the ball fields and run Music Bend Trail (almost two miles one way).

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