Cycling Mississippi - The Crooked Letter State

April 18, 2017 - Arlen Hall is Adventure Cycling's Tours Director

“M, straight letter, crooked letter, crooked letter, straight letter, crooked letter, crooked letter, straight letter, humpback letter, humpback letter, straight letter. That’s how you spell Mississippi.” How many of us learned how to spell the Magnolia State in this way?

Crooked and fun! That’s just how I would describe my recent crisscross ride around Mississippi with a four-day, Mississippi Department of Tourism sponsored, bike ride, celebrating Mississippi’s 200th anniversary and promoting cycling in Mississippi. 

You can do this ride too: Cycling Mississippi’s Bicentennial: 200 miles in the Magnolia State. And here’s more about cycling in Mississippi.

Our motley crew was comprised of:

Arlen riding the rails on the Tanglefoot Trail

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When it comes to cycling in Mississippi, the first thought that might come to mind is southern cooking and the famous Natchez Trace Parkway, running nearly 310 miles through the state — about 70% of the total length of the Parkway. This beautiful, low to mid, noncommercial trafficked roadway is predominately rural and traces the route that Native Americans used for centuries before European and American settlers used it for commerce along with the Mississippi River.

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However, Mississippi cycling has so much more to offer than just the Natchez Trace Parkway. Our tour began in New Albany, Mississippi, a trailhead for the Tanglefoot Trail. We were hosted at the beautiful Concord Inn B&B by owners Tanya and Chris Coombs. The elegance and charm of the south was evident in our accommodations and our meals.

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The 44-mile Tanglefoot Trail from New Albany to Houston, just off the Natchez Trace, can provide a small town alternate to the Trace from Houston and around Tupelo — heavy traffic, but a must see if you are an Elvis fan — via New Albany. You’ll have to do a bit of rural road riding from New Albany back to the Trace, but local cyclists know the way. And you may just find this trail as a “must ride” on Adventure Cycling’s Natchez Trace guided tour in the future. The trail features many “whistle stop” rest areas with flush toilets and running water, picnic tables, and easy access to many small southern towns with their traditional courthouse and park. Camping is available by contacting local towns and most have small motels.

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Pontotoc Town Square & County Seat

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Tired of camping? Try renting the One Night Stand just outside New Albany

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Typical riding conditions along the well-maintained trail, complete with easy access to many small towns with food, farmers markets, and coffee!

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A MUST stop is the Algoma Country Store midway along the Tanglefoot Trail.

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Algoma Country Store serving up my favorites of crispy wings, cornbread, fried okra, and plenty of southern sweet tea!

Next up was a sag over to Ridgeland, Mississippi, north of the state capital of Jackson, to share an evening meal with mayor Gene McGee and the Ridgeland Tourism Commission (RTC) and prep for the following day’s 35-mile ride around the beautiful Ross Barnett Reservoir along with a visit to the Mississippi Craft Center.

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Ross Barnett Reservoir

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Mississippi Craft Center featuring folk, traditional, and contemporary crafts along with demonstrations and workshops

Ridgeland, home to some of the most spectacular Natchez Trace riding, touts its own multi-use trail that connects to the Natchez Trace multi-use trail to detour bicyclists around the heavily trafficked Natchez Trace Parkway. Using Ridgeland as a home base, a cyclist can spend days riding the Natchez Trace (100 miles to Natchez), Ross Barnett Reservoir (35-mile loop ride), or the many rural roads in the area. The RTC sponsors or supports many one-day rides, along with other tourism events.

Next stop was a sag to Port Gibson via Rocky Springs, a ghost town and historic site along the Natchez Trace Parkway. From Port Gibson, we rode to 10 miles to the Windsor Ruins, built in the mid-1800s and burned to the ground in 1890.

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Windsor Ruins, the wrought iron stairs of which were moved to the first black, land-grant college in the United States: Alcorn University. Alcorn was the college my great grandfather attended at the turn of the 20th century.

We ended the long day with a jaunt up to Vicksburg, Mississippi where we dined in downtown Vicksburg at 10 South Rooftop Bar & Grill overlooking a riverboat on the Mississippi River and the beautiful Vicksburg courthouse.

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A riverboat cruises along the Mississippi River

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Downtown Vicksburg midweek: weekends bring live music to the bars and restaurants on the cobblestone streets of Vicksburg.

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The historic Warren County Courthouse (1858), now a museum with tours available

Early the next day, we crossed the highway and headed into the Vicksburg National Military Park. Here we rode a 16-mile loop with the owner of Crooked Letter Cycling. A great two-hour tour with many short, steep hills (the only hills of the week), led us over hills and dales, and through tunnels and trenches in the battlefield. At the visitor center, a short 25-minute film gives you a basic overview of the battlefield and the campaigns waged in the area. Even for the non-historically-minded riders, the tour was a short fascinating tour through history with personal stories of despair and hope. The siege of Vicksburg was the turning point in the American Civil War. Vicksburg is a mere 50 miles from Ridgeland, or 57 miles along the Natchez Trace and SR27 — easily reachable in a day.

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Entrance to the battlefield

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Union battle lines

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Bike Friday “Freddy” and Moulton bikes visiting the USS Cairo, installed in the park in 1977

Before leaving to cross the state for our next destination, the Longleaf Trace, my mind began churning on a potential new vehicle-free, inn-to-inn tour that includes Ridgeland, Vicksburg, Port Gibson, and Natchez, with layovers in all of these locations for opportunities for exploration of scenery, history and local cuisine.

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Rest area in Sumrall, Mississippi along the Longleaf Trace

One of several small towns along the Longleaf Trace

The Longleaf Trace, another 44-mile rail-to-trails conversion in the state, begins and ends in Prentiss and stretches to the third largest city in Mississippi, Hattiesburg. The Longleaf Trace is the first rails to trails conversion in the state of Mississippi and is used as a model for organizing trail development among multiple communities. The trail is in excellent condition, but services along the route are scarce. The most used section of the trail is within 15 miles of Hattiesburg.


Hattiesburg, Mississippi’s Longleaf Trace trailhead

Overnighting in Hattiesburg would be an excellent way of doing an out and back on this great trail. Accommodations and food in the town are outstanding. My meal for the night included sautéed brussel sprouts and tri-tail (triple tail) fish.

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Approaching the new bridge from Bay St. Louis to Pass Christian

We completed a magnificent week of riding in Mississippi along the beautiful Gulf Coast on a concrete boardwalk and some road riding from Waveland, Bay St Louis, Pass Christian, Long Beach, Gulfport, and Biloxi. Three of the riders that day were principals of schools destroyed by Hurricane Katrina; all told stories of courage and hope. It was uplifting to hear survival stories from those in the path of the storm.

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Gulf Coast near Waveland, Mississippi

The Gulf Coast beaches are protected by barrier islands and experience a fraction of the wave action that punishes much of the other beaches between Gulfport and Florida.

The Friendship Oak, a 500-year-old southern live oak tree has withstood the punishing hurricanes from the Gulf.

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Remaining school grounds for a Gulfport school destroyed in Hurricane Katrina.

The route can be a viable alternative to the Mississippi pine belt on the Adventure Cycling Southern Tier route. I can imagine riding the Southern Tier to the Mississippi River, heading south on the Mississippi River Trail (MRT) to New Orleans, then east across U.S. 90, then on local roads or the boardwalk to Waveland and beyond to Pascagoula.

Friendship Oak. The University of Southern Mississippi Gulf Coast

The last trail of the week was the Pascagoula Bike Trail in Pascagoula. This 10-mile route on historic city streets provided close-up views of lighthouses, inlets, bayous, the huge shipyard that increases the weekday population of the town by 20,000, and many historic homes and buildings. It was a nice leisurely ride to end a wonderful sample of cycling opportunities in Mississippi.

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Not Margaritaville, but it is Jimmy Buffet’s birthplace in Pascagoula.

My last southern dish of the tour was one of my favorites, shrimp and grits with plenty of Gouda cheese, Remoulade sauce, and bacon! It was unforgettable and a must stop off the main-coast route a few blocks.

Shrimp and Grits, Le Cafe Beignet, Rue Magnolia in Biloxi

Although I rode the south in March, many have said that cycling in the Deep South in late October and November can be just as spectacular. Adventure Cycling’s Natchez Trace Fall, van-supported tour, October 29 through November 5, along with a few side trips, will offer up a good dose of southern hospitality.

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Finishing off the week with Chicory and Beignets in Biloxi

Check out some awesome video from our weeklong tour, captured and narrated by The Path Less Pedaled! You can find more detailed information on all the sites I visited by bicycle at Visit Mississippi, Visit Ridgeland, Visit Vicksburg, Tanglefoot Trail, Longleaf Trace, Visit Hattiesburg, and Visit MS Gulf Coast. Thank you Mississippi Tourism. I’ll be back, Mississippi!

Laissez Les Bon Temps Rouler!

Photo 1 by Saara Snow | All other photos by Arlen Hall


ON THE ROAD is written by the tours team— Paul, Mandy, Emma, Mike, and Arlen — tours specialists and intrepid bicyclists, helping you bring your cycling dreams to fruition. Check out our 2018 Guided Tours today!



DoubleD September 7, 2017, 4:25 PM

Mississippi is a wonderful cycling state.

Lots of wonderful food to be had in the south land but my absolute favorite is a big mess of yellow grits early in the morning with plenty of butter. Grits is groceries!

Alan hellmann April 20, 2017, 7:07 AM

How did the cars treat you on the road?

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