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Derby Week in Kentucky

African American jockeys once dominated the track. But by 1921, they had disappeared from the Kentucky Derby


On May 7, racegoers will marvel at jockeys perched on metal stirrups in perfect sync with 1,000 pound thoroughbreds running at 40 mph. Trainers and owners fight over these top riders for major international races.

And arguably the first superstar jockey on an intercontinental scale was Kentucky-born, two-time Derby winner Jimmy Winkfield. He dominated racetracks spanning a quarter of the globe, earning $100,000 a year in the early 1900s. Winfield rubbed shoulders with royalty, married an heiress, and counted Josephine Baker, Bing Crosby and Paul Robeson among his admiring friends. His fantastic saga, with all the backside intrigue and fortunes changing hands against the backdrop of 20th century war and upheaval, is performed live each night of Derby week in the play JOCKEY JIM. Last of the great black jockeys, Winkfield won the Derby in 1901 and 1902, then went to Russia and became a national phenomenon. 

winkfield 2

He helped evacuate the racing community during the Bolshevik revolution, relocated to France, and was a prosperous trainer until Nazi occupation during World War 2 forced his return almost destitute to a racially segregated America, where black jockeys had become unknown figures of a forgotten past. Suddenly the famous black horseman and his aristocratic wife were transformed into a stable hand and domestic servant, struggling to hold together a mixed marriage that was illegal in most states. Though haunted by ghosts of greatness past and ridiculed as a lunatic and preposterous liar, Winkfield used competitive drive and equestrian genius to overcome bigotry and reclaim a forgotten legacy.

For another tidbit about horse racing in early Kentucky see the Video about William Whitley.


New Event

Stanford, Kentucky Rallies to Finish Rebuilding Logan’s Station


May 19-21, 2016 The Siege of Logan’s Fort 1777 will be held in Stanford, KY Events include a Downtown History Walk, and a re-enactment of The Siege of the fort. Efforts will be used to finish the rebuilding on the fort that has to date been only partially completed.

Logan's Fort was set on a slight elevation about fifty yards west of the smaller spring at St. Asaph. The fort was 90 X 150 feet and was constructed of logs. Gates were located at each end and were raised and lowered by leather thongs. Logan's fort is currently in the process of being rebuilt.

Upcoming Events for 2016

May 13-15, 2016 The Raid at Martin’s Station, Wilderness Road State Park, Ewing Virginia
May 19-21, 2016 The Siege of Logan’s Fort 1777 will be held in Stanford, KY. Events include a Downtown History Walk, and a re-enactment of The Siege of the fort. Fund raising efforts will be used to finish the rebuilding on the fort that has to date been only partially completed.
May 21, 2016 Civil War fort at Boonesborough .Living History Event 10-AM to 3 PM Learn More...
May 20-22, 2016 Siege of Fort Randolph, Krodel Park, Point Pleasant, WV School Day - Friday , other activities, battle re-enactment 2 PM Saturday only.
May 28-29, 2016 Spring Trade Days - Fort Boonesborogh State Park, Richmond, KY Learn More...
May 28-29, 2016 Spirit of Vincennes Rendezvous- Vincennes, IN

History in Our Own Backyard

DSC04972wright air flight

A visual visit to the United States Air Force Museum at Wright Patterson Air Force Base in Springfield, OH. Click here....

The Cumberland Gap Event - The National Parks Celebrate 100 Years with a National Quarter Release


Re-Enactors gathered on April 9, 10 and 11 to commemorate the 100th Anniversary of The National Parks System. The 3 day event consisted of an encampment for visitors on Saturday and Sunday, a special twilight visit to the Gap for re-enactors on Saturday evening and the unveiling f the new Commemorative Quarter on Monday in the presence of almost 2,000 school age visitors. Learn More..

New Event Calendar Format

The Pioneer Times has a new format for our event calendar. Click here to view the calendar.

Submit your events to our new calendar. Please submit any events through this link. All living history events may be submitted.

In addition to the calendar any events submitted will appear in an online searchable database. This will allow you to search for an event that you may not know the date. Click here to see the database.


Women on the Frontier 2016


April 16 and 17 brought the 12th Annual Women on the Frontier event to Fort Boonesborough. A weekend dedicated to learning - this event gives women re-enactors and their families a chance to learn more about the frontier. This years theme was Food and Shelter. Attending women and visitors to the fort were schooled in frontier gardening, and shelter building. Saturdays events included a hands on building of a shelter from willow saplings. Photos Coming Soon!

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Chief Black Hoof
 Visits the Painted
Stone Settlers

Each spring The Painted Stone Settlers of Shelbyville, KY present a first person speaking event to the community. Well known for their re-enactment of The Long Run Massacre each fall the group added the spring event in 2009.

We realized that not everyone can make the fall event and the fact that it is an outdoor event hampers some folks in the community. As our mission is education - the spring event was a way to expand that mission, said Helen mcKinney of PSS.

On April 14, Chief Black Hoof (Catahecasa) brought his story to The Stratton Community Center. His was a long life and one that not many people are familiar with. Known as a great orator among the Native peoples Black Hoof took a different view on the American than did many of his contemporaries.

Springfield Ohio native Rusty Cotrell brought the Chief to life with his portrayal. More photos and story to come.....

History in Our Own Backyard


An early spring in Kentucky had us heading out - cameras in hand looking for history in our own back yard. Just across the Ohio River in Southern Indiana was a little known set of murals in Jeffersonville along with this monument to Lewis and Clark outside The Falls of the Ohio State Park. Statue at Clarksville, Indiana  Murals at Jeffersonville, Indiana

Penix plans Boone Trace Hike in
conjunction with Cumberland Gap Spring Event

In 2015 Curtis Penix planned and completed a hike of a portion of the Boone Trace. Penix is an avid hiker and was interested in learning more history about the trek. His hike was documented on his website and concluded at Fort Boonesborough on April 2015. Many people followed the event and even joined in the hike. See the story from 2015. This year Penix is going to make the trip in the reverse of his 2015 hike beginning at Fort Boonesborough and is inviting re-enactors and anyone interested in the trip.


Hikers starting out from Fort Boonesborough early on April 2, 2016.

Dr. John Fox and the Friends of Boone Trace have been working tirelessly this past year with organizations at the local, state and national level to open Boone Trace as a recreation and education destination. Last year’s hike from Kingsport, TN, to Fort Boonesborough, KY, was just the beginning.

Go to and (check out the digital maps page) and start following the hike.


A volunteer from the audience learns about surveying.

Fireside Chat with David VanMeter,
Surveyor at Fort Boonesborough

The third of the February Fireside Chats took place at Fort Boonesborough State Park on February 27, 2016. David VanMeter portrays a Frontier Surveyor in an era when surveying was of paramount importance. With land opening up in Kentucky and land warrants available to former military everyone wanted the best land in Kentucky.

VanMeter brought his tools of the trade and entertained audiences with both the technical and period aspects of surveying. At left he is shown with a volunteer from the audience and is helping her “sight” the coordinates.

The weather was balmy for this chat and it was a full house for the Frontier Fare dinner of burgoo and cornbread. Folks were able to mingle outside and visit the tavern and 18th Century Transylvania store before the performance.

This chat followed last week’s Mel Hankla as General George Rogers Clark and the February 6 Chat of Undressing the Historical Lady by Maggie Waterman Roberts (photos available).

Next week, March 5 brings Daniel Boone (Kevin Hardesty)to the fort. Boone was originally scheduled for February 13 but was rescheduled due to weather. There are still a few remaining seats left for this final performance - reservations are available at 859-527-3131.

Click here for more...


The Fireside Chats 2016
Undressing the Historical Lady

The Fort Boonesborough Foundation hosted the first of the February Fire Side Chats on February 6, 2016.

The opening performance was a lecture by Maggie Waterman Roberts entitled “Undressing the Historical Lady. “ The well dressed and equally knowledgeable Roberts explained with humor and tact just how many layers an 18th century woman wore.

Along the way she shed various layers, taked about their construction and how each piece developed as a common wardrobe staple. Each garment landed on the table next to her so visitors could come up to the front after her talk and examine the stitches and construction.

Additional Photos

The Kentucky Bookfair
  Frankfort, KY November 2015

One of the events that we covered in late 2015 was the Annual Kentucky Book Fair. Now in it’s 34th year we were in attendance with an estimated 4,600 other people at the Frankfort Convention Center. More than 200 authors and illustrators participated in the fair, signing their books and taking part in symposiums and panel discussions.

Authors have long been a major source of both interest and information among living historians. There is no better way to obtain quality information than to meet with an author that has thoroughly researched the subject or time period that you are interested in.

See photos and story......

book fair 15


The Re-Enacting World loses an original

Wayne Milton passed away on December 23, 2015. There were complications after his surgery, and he had been in the hospital 45 days. Most of that was in a drug induced coma in a ventilator.

Wayne was a long time re-enactor. He portrayed Daniel Boone among his many personas. The last chance we had to visit with Wayne was at The Siege of Boonesborough in September. He had been battling cancer and talked of an upcoming surgery that was scheduled. He was able to see many old friends that weekend and stopped to talk with all of them. Wayne leaves his wife Kathy Johnson Milton, 2 children and four grandchildren.

In 2010 we did a photo spotlight on Wayne Milton at Martin’s Station. Click here to see these photos of Wayne at his best. His obituray can be found at

All stories and event photos from 2015 have moved.
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