Pony Express tradition from Canaan to Madison continues for 58th year

Sep 20, 2025

1 min read

Photos provided by Jo Shelley

(CANAAN, Ind.) – One of the most unique traditions you’ll find in Southeast Indiana took place on Saturday.

It’s a tradition that shines a light on a time in American history when mail was carried by horses, known as the Pony Express.

The small community of Canaan pays homage to that era every year during their annual fall festival.

On Saturday, a group of eight horse riders took a 14-mile trip from Canaan to Madison to deliver real, actual mail.

This year’s ride was organized by Rayna Mashburn who works at the Canaan Post Office.

The eight horse riders began the day by participating in the Canaan Fall Festival Parade.

That was followed by a ceremony where they were each sworn-in as United States Postal Service mail carriers.

The horse ride left Canaan around 1 p.m. and arrived at the Madison Post Office around 4 p.m.

“One of my favorite things was seeing the excitement on the kids' faces whether in the parade, the swearing-in ceremony or even along the pony express route,” said rider Jo Shelley.

This was the 58th annual ride and the Canaan to Madison route is believed to be the only Pony Express tradition east of the Mississippi River that continues today.

Those who paritipcated in the ride were Jo Shelley, Nicole Jones, Blake Jones, Emily Hebert, Ashley Colley, Benny Diggs, Whitney Burdzilauskas and Trenton.