Trail ride planned along the historic Miles City to Deadwood Trail |

Trail ride planned along the historic Miles City to Deadwood Trail

Courtesy photoThe Miles City, MT to Deadwood, SD historic trail ride will cover 200 miles and culminate in a celebration and a stroll down Deadwood's Main Street.

Organizers in Montana and South Dakota are planning a historic ride with horse- and mule-drawn wagons and saddle horses in late August and September along the Miles City to Deadwood Trail to commemorate the famous route that was used in the late 1800s as a link between the two frontier towns. The adventure turns time back to early days in the Old West when challenges lurked around every turn.

The 200-mile ride is scheduled leave from the Custer County Fairgrounds in Miles City, MT on Aug. 20 and arrive in Deadwood on Sept. 4 with three rest days planned along the way. The route goes through Montana, Wyoming and South Dakota. Actual travel distance each day is expected to be about 18 to 20 miles with eight to ten hours required in the saddle or on the wagons. People are welcome to walk as well.

The famous trail, which actually started at Fort Keogh cavalry post, was mapped out by Yellowstone Kelly as a telegraph line in 1878 just two years after the rough-and-tumble Deadwood Gulch mining camp was established. It ended at the Fort Meade cavalry post that was established to protect early settlers and miners.

Until 1887, historians say the trail served as a tri-weekly mail and freight route through the territory. It is believed that Calamity Jane, who spent time in both towns, was among the people who used the trail. It was reported that few travelers were present on the route but horse thieves and highwaymen frequented the trail.

“It’s a one-time project to get historic recognition for the trail on the National Register,” said co-chairman Michael Greslin of Sturgis, SD. “This trail is full of history and the ride will be an adventure and a hands-on, colorful lesson for all participants because the ride will cover unique terrain, with most areas unchanged since the trail’s inception.”

Organizers hope that other historic trips can be planned to obtain recognition for other historic trails like the one from Bismarck to Deadwood.

Greslin said the organizers wanted it to be a family affair to promote the history of the trail and our Western pioneer heritage. The ride has been planned for about a year and a half by a board with members located in Montana and South Dakota.

The route begins by heading south on Highway 59 to Beebe which is an old stage coach stop. On the second day the ride goes to Powderville where there will be the first of the day-long rest stops. After that, the route goes cross country to Box Elder Creek and then to Alzada for the second day-long rest stop. After the rest stop, the trail goes south and west across the Belle Fourche river bottom and enters South Dakota in the vicinity of Aladdin. The third rest day is planned for a ranch west of Belle Fourche. After that, the trail heads toward Spearfish and then on to Deadwood, Greslin said.

The route covers both public and private land and some current roads because a number of roads have been constructed over the top of the trail, Greslin said.

When the riders enter Deadwood On Saturday, Sept. 4, they will ride down the city’s Main Street. A trail’s end celebration is planned in Deadwood.

The board plans to have programs with special features, entertainment and speakers each evening after the group sets up their camp.

In addition to Greslin, other board members include: Alan Loken, Whitewood, SD; Jon Mattson, Deadwood, SD; Kevin Kuchenbecker, Deadwood, SD; DJ and Jan Cornett, Miles City, MT; Laura Ragland, Miles City, MT; Gloria Rosencranz, Boyes, MT;, Lester Phillippi, Hammond, MT; Jim Dacar, Belle Fourche, SD; and Ron Raber, Belle Fourche, SD.

The major sponsor is the Days of ’76 museum in Deadwood.

Dr. Jim Curtis of Malta, MT is serving as the wagon boss.

Under the format, riders may sign on to ride for the entire distance, or choose a specific day in which to participate. It is limited to 300 participants with applications accepted on a first-come, first-served basis.

Fees collected for the ride will go to cover water for animals, portable toilets, transportation to and from evening camps and the end of the trail celebration.

Greslin said participants are responsible for hay, grain and transportation for their stock.

For more information, or to get an application, contact the Deadwood Chamber of Commerce at or contact Michael Greslin at 605-787-5501 or

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