Tanglefoot Trail Itinerary


At a Glance

Name: Tanglefoot Trail
Length: 43.6 Miles
Trail activities: Bike, Inline Skating, Wheelchair Accessible, Walking
Counties: Chickasaw, Pontotoc, Union
Surfaces: Asphalt
State: Mississippi

About this Itinerary

Meandering through the foothills of the Appalachian Mountains is the 44.5-mile Tanglefoot Trail. Not only is the Tanglefoot Mississippi’s longest rail-trail, it also courses though the Mississippi Hills National Heritage Area and traces a route imbued with history. The trail preserves the abandoned railroad corridor assembled in part for the Gulf and Ship Island Railroad by Col. William C. Falkner, the great-grandfather of Nobel-Prize-winning author William Faulkner. Long before the rail, however, the pathway was used by Chickasaw Indians and was dubbed the King’s Highway, after the last Chickasaw king.

Today, the asphalted trail winds through three counties and connects six rural communities while offering scenic views of mature hardwood forests, farmlands and pastures. Between New Albany and Houston, recreationalists can enjoy a level, gentle trail with ample access to amenities either at the whistle stop comfort stations (four on route with restroom facilities) or towns along the way. We suggest a two-day round-trip ride beginning and ending in New Albany, the northern trail terminus. Air travelers will come to the area via theMemphis International Airport, 70 miles northwest of New Albany, or the Tupelo Regional Airport, 23 miles southeast of town. Renting bicycles for the ride is easy and convenient at Trails and Treads, just blocks away from the trailhead.

Located on the banks of the Tallahatchie River, New Albany is a charming town with much to offer its visitors. The historic downtown area features antique stores, eateries, parks and specialty shops. The Union County Heritage Museum is a must-see for those interested in learning more about the region’s past— including the Chickasaws, the first European settlers and the Civil War Reconstruction. Stroll through the beautiful William Faulkner Literary Garden, located a block away from the writer’s birth site, and immerse yourself in a landscape that reflects Faulkner’s words and sentiments for his native home. The museum also provides tours of the Ingomar Mounds, a ceremonial and burial complex dating back to the “Middle Woodland” period around 100 B.C. to 400 A.D.

In addition, New Albany sponsors some pretty interesting festivals and events that may well influence the timing of your trip. For example, the town celebrates spring with the Mississippi Bluegrass Championship and ushers in autumn with the Tallahatchie River Fest, a lively celebration of art, music, film and literature.

Once you work up an appetite for southern cuisine, head to Tallahatchie Gourmet for a crawfish Po-Boy or shrimp and grits. Another local favorite, Taylor’s Fish and Steak House, is on the outskirts of town but the place to go if catfish, frog legs or fried quail sounds good to you. There are BBQ joints, delis and a bakery in town so something for most tastes and places to go for sandwiches or snacks for the ride. Oh, and don’t forget the Biscuit and Jam Farmers’ Market each Saturday during the growing season— you can’t find a better place to appreciate the local produce and folk arts from the hill country. Ever tried Sweet Magnolia ice cream before?

The lodging options don’t offer as much in the way of local flavor and flair, but there are quite a few hotels in the vicinity, most one to two miles west of downtown and the river. Here are a few options: Comfort Inn, Hampton Inn and Holiday Express Inn.

Settle in and enjoy your time in this historic region. Just a heads up: there is so much of interest to discover in the greater Mississippi Hills National Heritage Area, from Civil War sites to the birthplace of Elvis Presley, that you will want plenty of extra time in your itinerary to explore the nearby towns and national forests as well.

Day 1

The trail begins next to the Union County Library where a trailhead is planned for the future. For the first mile you cycle past residential neighborhoods and industrial buildings. After traversing Highway 78, you are quickly surrounded by woodlands and the trail feels fairly secluded for the next two miles until you cross Kings Creek where the landscape begins to open up. There are several public road crossings and you will parallel County Road 90 for the last two-mile stretch before arriving in Ingomar.

The old rail corridor you are traveling through came to this area in 1886 and the trail is actually named after a narrow gauge engine, the Tanglefoot, which performed especially well during the construction of the railroad. If you are a rails-to-trails enthusiast, you will certainly know that the undertaking of early rail line development often resulted in stories of intrigue, scandal and some serious financial maneuverings and power-plays. It would seem that Colonel Falkner’s story about accomplishing his dream of building a rail line is no different— too long to go into here, but the historical picture of this time, provided by the Tanglefoot Trail site, is definitely worth the read. Colonel William C. Falkner also was a writer and the community of Ingomar (mile 6.5) was named after a fictional Chickasaw Chief character in one of his books.

South of town, approximately half a mile off the trail, west on County Road 96, is the Ingomar Mound site. It is free and open to the public. Remaining on the trail, a bridge will take you over Okannatie Creek. You may have already noticed trees draped in the vines of kudzu (an invasive species) and the ubiquitous fields of cotton and soybeans. Much of the splendor of this route, however, comes from imagining all those who utilized this pathway before you. Historians believe that early explorer Hernando De Soto traveled through this hilly region in 1540 and may have made his second camp at the Ingomar Mound site. Later, Meriwether Lewis came through the King’s Territory on his way to the Chickasaw Agency.

In Ecru (mile 11), the trail crosses Main Street where there are shops and eateries if you need water or snacks, though the next town of Pontotoc (6.8 miles farther) offers a larger variety of restaurant options. Except for a major road crossing (Pontotoc Parkway W.) about midway between these two towns, you will have plenty of uninterrupted time to become familiar with the sights, sounds and smells of rural Mississippi. You are also traveling through what is considered to be the heart of the Chickasaw Homeland. The Chickasaw are believed to have settled in the area in 1650 until they ceded their land to the U.S. government in 1832 through the Indian removal treaty, the Treaty of Pontotoc.

Town Square Post Office & Museum

The Town Square Post Office & Museum in Pontotoc (open Monday-Friday and located on Main St.) retraces some of this history as well as houses railroad and early European settler memorabilia. Of particular note is the mural in the museum’s lobby which depicts the first recorded Christian marriage in America; this marriage was between Juan Ortiz and Se-Owana, a Seminole princess, and is said to have taken place in this area during Hernando de Soto’s visit. Explore this historic small town and take time to enjoy a meal; you are nearly half-way through your day’s ride. bT’s is a couple blocks north of the museum on Main Street and a good place for burgers or sandwiches. To get to Main Street from the trail, take Coffee Street east to W. Marion St. You may notice the office of the Three Rivers Planning & Development District on Main Street as well; wave to the good folks as you go by as they are part of the team that made the Tanglefoot rail-trail what it is today. Also, the Hill and Trail Bicycle Company is in Pontotoc and offers bike rentals as well as rescue service should you run into bike-related difficulties on your journey.

The trail cuts primarily through an agrarian landscape and there may be an occasional deer, fox or squirrel that crosses your path and certainly plentiful birdlife around you as you weave in and out of woodland patches and sidle up to fields and creek bottoms. The small community of Algoma, mile 24.3, once flourished after the arrival of the Gulf and Chicago Railroad with the growth of its timber industry as well as an impressive tie factory. Today, you see little evidence of these industries though Algoma still celebrates its one-time tie notoriety with the annual “Cross-Tie Festival” held each October. There is a country store on Algoma Street and a chance for more catfish and a seafood buffet at the Seafood Junction (Front St.).

In another 9.5 miles, Chickasaw County’s oldest non-Native settlement is now part of New Houlka (mile 33.7). The original “Old Houlka” was established in 1812 at the intersection of the Natchez Trace, a historic Native American trail, and the Gaines Trace, a section of the trail that was surveyed by the Gaines brothers and later became a road connecting the Tennessee River to the Tombigbee River. Take a moment to rest at New Houlka’s Whistle Stop and try to fathom the immense history that lives in the memory of these hills. Though you won’t have easy access from the trail, keep in mind that more ancient ceremonial mounds are located in the area between Houlka and Houston: the Owl Creek Mounds (built between 1,100 and 1,200 A.D) and the Bynum Mounds (roughly the same period as the Ingomar Mounds). All three of these sites are on the National Register of Historic Places.

The final 10-mile stretch of the trail is a straight shot south to Houston (mile 43.6), with little to impede the journey. You can anticipate several country road crossings and a major crossing at the Houston Bypass but, otherwise, savor the quietude of the Mississippi Hill’s rural nature and the ease of this well-maintained trail. The southern terminus of the trail is in Houston on West Church Street where, again, a trailhead is planned for the future. You might arrive in Houston in time to enjoy some small-town festivities such as their annual 4th of July Celebration on Pinson Square or the bi-annual Flywheel Festival held each spring and fall, where anything with wheels could be on display, including antique tractors and old steam engines.

Just before the trail ends, head east 1.5 miles on Madison Street to the Holiday Terrace Motel to begin unwinding for the evening. Houston is home to the nation’s first library and you may notice the Carnegie Library (circa 1909) as you ride down Madison Street. You will also pass most of Houston’s restaurants on the way, either on Madison or Jackson Streets, but don’t expect a large selection to choose from.

Day 2

Today, you return to New Albany via the same route, but with a northerly perspective so who knows what new adventures lay ahead!

Attractions and Amenities

Restaurants, Wineries, Ice Cream, Pubs

Nearby Trails

Tupelo Veterans Park Trail

Mississippi - 0.9 miles

Tupelo's Veterans Park Trail is a short multi-use trail that runs through the city park, just across the way from the birthplace of The King himself,...

Oxford Depot Trail

Mississippi - 1 miles

The Oxford Depot Trail is part of a planned network of trails linking the community of Oxford. The centerpiece of phase 1 is two segments of the...

South Campus Rail Trail

Mississippi - 2.8 miles

The South Campus Rail Trail, formerly known as the Thacker Mountain Rail-Trail, is part of a network of trails linking the community of Oxford. This...


Wolf River Greenway

Tennessee - 12.4 miles

The developing Wolf River Greenway will one day span 36 miles, connecting downtown Memphis, the north-central neighborhoods of the city, Shelby Farms,...

Shelby Farms Greenline

Tennessee - 10.6 miles

The first phase of the Shelby Farms Greenline opened in 2010 and helped inspire a new culture of biking and walking in Memphis. About 200,000 people...

Kitty Bryan Dill Memorial Parkway National Recreation Trail

Mississippi - 2.2 miles

The Kitty Bryan Dill Memorial Parkway is a narrow concrete path that runs for over two miles through the eastern Mississippi community of West Point —...

V&E Greenline

Tennessee - 1.8 miles

It has been said that it takes a village to build a rail-trail. In the case of the 1.8-mile V&E Greenline, the village in question is the...

Locksley Way Multi-Use Path

Mississippi - 1.1 miles

Picking up right where the Lynn Lane Multi-Use Path leaves off, the Locksley Way Multi-Use Path provides a crucial connection for cyclists and...

Lynn Lane Multi-Use Path

Mississippi - 1.5 miles

This shared-use path in Starkville stretches from McKee Park in the west to Montgomery Street in the east. While providing a space for leisure or...

Riverbluff Walkway

Tennessee - 1.2 miles

The Riverbluff Walkway offers scenic views of the Mississippi River as it traverses the edge of downtown Memphis. The trail is built on top of the...

Big River Crossing

Arkansas - 1 miles

Big River Crossing, which officially opened on October 22, 2016, connects downtown Memphis, Tennessee, with West Memphis in Arkansas along the north...

Columbus Riverwalk

Mississippi - 2.2 miles

Closure Notice: In February 2020 the pedestrian bridge over the Tombigbee River was closed due to damage to a support pillar, with no estimate for...

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple


Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple


Your account has been deleted.