The Cycling Culture

North Mississippi’s vibrant and diverse cycling community welcomes road and mountain bikers of all skill levels to participate in weekly rides, events and activities that promote the

growing sport.

Written by Dawn Denham  |  Photos by Joe Worthem

Whether you prefer road, gravel or mountain biking, north central Mississippi offers plenty of ways to get on two wheels. From paved rail trails and quiet country roads to hand-built singletrack, the region has become a destination for cyclists of all ages and skill levels — and the local cycling community is growing right along with it.

Oxford’s cycling scene is particularly active, with weekly group rides, mountain biking clubs, gravel events and ongoing efforts to expand trails and connect existing bike routes. For newcomers, riding with a group is one of the easiest ways to get started. For experienced cyclists, there’s no shortage of challenging roads, hills and trails to explore.

The region’s cycling infrastructure has deep roots. At the end of the 19th century, north central Mississippi towns existed because of mills, farms and rail lines. Today, some of those former rail lines have found a new life as recreational trails, connecting communities and giving cyclists a chance to experience the landscape in a whole new way.

The Tanglefoot Trail, located in the Mississippi Hills National Heritage Area, follows 44 miles of the old Gulf and Ship Island Railroad, once owned by our own Falkner family. The Long Leaf Trace stretches 44 miles along the former Mississippi Central line, beginning in downtown Hattiesburg and ending in Prentiss.

Since opening in 2013, the Tanglefoot Trail has become a major destination. It was named one of 10 new National Recreation Trails in 2015 and voted into the Rail-Trail Hall of Fame in 2019, helping drive economic development in the three counties it crosses. Its success has inspired other communities to transform former rail lines into paved, multiuse trails.

In Oxford, the multiuse Oxford Depot Trail runs from Molly Barr Road to the historic Oxford Depot over Jackson Avenue and connects with roads that have designated bike lanes. Oxford’s commitment to cycling has earned the city recognition from the League of American Bicyclists as a “bicycling friendly city.”

These paved paths are used daily by people of all ages and backgrounds for recreation and sport, including cyclists who travel from out of state, and they are continuing to expand. Plans are underway to extend the Tanglefoot Trail 20 miles north from New Albany to Ripley. In Oxford, efforts are focused on improving and creating parks, connecting existing multi-use paths and designated bike lanes and building new trails. The Yalobusha Greenway Alliance, a nonprofit based in Water Valley, is working to convert the former Illinois Central line from Grenada to Holly Springs, through Taylor and Oxford, into a multiuse park. The organization currently maintains nearly 2 miles of the Yalobusha Greenway in downtown Water Valley.

According to TrailLink by Rails-to-Trails Conservancy, “Cycling in Mississippi grew out of old rail and farm roads and has turned into an organized, fast-growing scene built around rail-trails, singletrack, and quiet rural pavement.”

That description fits: Whether you’re looking for a leisurely ride, a challenging climb, a fast group road ride or miles of gravel and dirt, there’s a route — and a community — to help you find it.

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Road Riding

For those seeking that “quiet rural pavement,” north central Mississippi offers “some of the best road cycling in the state, including hills for climbing,” said Claude Gunter, founder of Oxford’s Velvet Ditch Gran Fondo, an annual multi-distance ride.

The region’s rolling hills and natural beauty make a 25- to 50-mile ride a welcome challenge, but sharing the road requires awareness from both cyclists and drivers. Gunter said today’s technology has made road cycling safer than many people realize. Side mirrors, magnetic lights, radar systems and reflective clothing all give riders additional tools to stay visible and aware of their surroundings.

Most state, county and town roads in Mississippi still lack bike lanes or even generous shoulders, yet cyclists of all ages and abilities regularly take to the open roads of the Hill Country, often in groups. Sital Sigh, an avid cyclist whose husband and children also ride, joined several local riding groups and felt welcomed immediately.

“The barrier,” she said of cycling in Mississippi, is being alone. “I worry about safety, and here, you can always be part of a group.”

That sense of community can make all the difference. Dogs, fast drivers and motorists who are unfamiliar with or fail to follow Mississippi’s safe-passing law can add risk to what some consider an inherently vulnerable pastime. But there is strength in numbers. Local cycling groups offer support, camaraderie, clinics and a variety of riding experiences, from no-drop and fast rides to trail and gravel rides.

Oxford Cycling hosts group rides that depart from Oxford throughout the week. The “B-Team” rides on weekend mornings from Yocona Ridge and Plein Air in Taylor and on specific weekday afternoons from M-Trade Park. Additionally, the “A-Team” rides daily and welcomes experienced riders looking for a fast and reputably tough group. Local cyclists also lead pop-up rides on Tuesday and Thursday evenings.

For current ride information, visit Oxford Cycling’s Facebook page. New riders are typically added to GroupMe threads for individual riding groups, making it easy to find a ride that matches your experience.

On the Dirt

Mountain biking has a long history in Oxford and the surrounding hills — in fact, the sport took hold here first. The Whirlpool Trails offer a diverse network of dirt and mountain bike trails, while the South Campus Rail Trail provides a 2.5-mile gravel corridor that’s popular with mountain bikers as well as walkers.

Oxford and Lafayette County have expanded and refined two major singletrack systems, with more than 35 miles of hand-built trails ranging from beginner-friendly routes to challenging terrain for experienced riders. Paired with nearby forest roads and rolling farmland, these trails allow cyclists to mix pavement, gravel and dirt in a single ride, helping establish the Hill Country as a mid-South mountain biking destination.

The North Mississippi Gnarmadillos Mountain Biking Team, based in Oxford, gives middle and high school riders the opportunity to learn, train and compete through the Mississippi Interscholastic Cycling League (NICA). The club emphasizes health, strength and inclusion while giving student-athletes opportunities to serve their community through trail maintenance and stewardship. A girls’ program actively encourages more female riders and coaches to join the sport.

Gravel Gets Growing

Gravel riding — which combines smooth pavement with rough dirt roads — is currently the fastest-growing cycling style in the U.S. Riders are drawn to the freedom and relative solitude of gravel roads, the variety of distances and terrain, and a community that tends to emphasize fun and camaraderie over the intensity of elite competition.

North Mississippi has plenty of gravel, with rides organized by cyclists throughout the region from the Memphis area to Collierville, Hernando, Oxford and Tupelo. Gravel bikes are built specifically for this type of riding, with features that set them apart from both traditional road and mountain bikes.

The North Mississippi Gravel Rides Facebook page posts about group rides on various trails, including Ashland and Potts Camp. As one avid gravel rider puts it, “There’s good gravel to be had out on Highway 30E in the Holly Springs National Forest as well as in Water Valley South of Enid Lake.”

No matter your discipline — or your bike — there’s a place for you in north Mississippi’s cycling community. Seasoned cyclist or first-time rider, roadie or mountain biker, gravel enthusiast or trail explorer, there are clubs, group rides and local bike shops ready to help you find your way.

Get in the saddle, turn the pedals and enjoy the wind in your face. There may be no better way to experience the beauty of Mississippi.

Save the Date

Ride with like-minded folks in noncompetitive, multi-distance events benefitting local causes and organizations:

Sept. 26: Tallahatchie River Ride, New Albany: visitnewalbany.com/tallahatchie-riverfest

Oct. 10: Tour de Bodock, Tanglefoot Trail: tanglefoottrail.com

Also mark your 2027 calendars for these popular annual rides: the Natchez Trace Century in May in Jackson; Pedaling for Hope and Ride for the Light in June on the Tanglefoot Trail; Bikes, Blues & Bayous in August in Greenwood; and the Velvet Ditch Gran Fondo in August in Oxford.

Find Your Ride

Oxford Cycling hosts informal A-Team and B-Team group rides throughout the week that are open to anyone. There are weekend options as well as afternoon and evening weekday rides. Find the most updated information at facebook.com/OxfordCycling.

The website rideoxford.com compiles information on local group rides, upcoming cycling events, cycling clubs and more.

In Tupelo, group rides take place Tuesday and Thursday evenings and Saturday mornings. Find information at corecycleandoutdoor.com/group-rides.

Core Cycle + Outdoor has locations in Tupelo (1697 N. Coley Rd.) and Oxford (1009 N. Lamar Blvd.) Check them out for gear, apparel, footwear, helmets, maintenance and repairs.

The Ole Miss Bike Shop, located in the Department of Transportation building at 980 Whirlpool Drive Suite A, is helmed by long-time MRB enthusiast and advocate Steve Valliant and offers student and staff rentals, repair and maintenance. Valliant, a dedicated trail maintenance volunteer, organizes the annual MTB Cry Baby Time Trial and other events.

Find information on services offered through the bike shop, safety tips and more at olemiss.edu/parking/bike-page.

Keep up with the Gnarmadillos youth mountain biking team by following them on Facebook or contacting them at northmsnica@gmail.com. 

Support the organizations working to expand trails in the area, such as Tanglefoot Trail (tanglefoottrail.com) and Yalobusha Greenways Alliance (yalobushagreenways.org) by attending their meetings, donating or volunteering at events.