Welcome to Ridgeland’s FourthAnnual OBO…Mississippi’s Premier Tandem Rally. We are  “One Behind the Other” in discovering Ridgeland, Mississippi and a weekend full of cycling, food and festivals.

2018 Date Is Set!!!!

 April 6-8, 2018!!

More information and registration will be coming soon, but check out the 2017 itinerary to see what the weekend has to offer!!

Contact Michelle Williams at michelle@crookedlettercycling.com or 601-573-2057..


The weekend of April 6-8, 2018 will feature some of Central Mississippi’s fantastic cycling routes with the main feature ride being around the Barnett Reservoir and  the Natchez Trace Parkway, a national scenic byway of the National Park Service that runs right through the City of Ridgeland.

Also presented this weekend will be the 10th Ridgeland Fine Arts Festival showcasing 11 mediums of visual art from 100 artists from across the United States as well as the Sante’ South Wine Festival featuring 30 winemakers from across the world Events will take place at Ridgeland’s beautiful Renaissance at Colony Park and Township at Colony Park. Rides, Music, Art and Wine….an exciting combination. You don’t want to miss this premier event in one of Mississippi’s and the South’s hidden jewel communities.

A designated Bicycle Friendly Community by the League of American Cyclists, Ridgeland also hosts the Natchez Trace Century Ride in May and offers its residents and guests a high quality of life and outdoor adventure visitor experiences with the Ridgeland Multi-Use Path and the Barnett Reservoir.

Cycling amenities, events and activities are an important attribute to the City of Ridgeland.  We are excited to share that Mayor Gene McGee who is an avid cyclist will be a participant in the 2018 Ridgeland OBO Tandem Rally.


Average high temps in April are 73-79 degrees and average lows are 53-58 degrees.



Click the icon for more information on Ridgeland Fine Arts Festival and Sante’ South.