The headlights from the pickup behind her horse on a dirt road between Lingle and Fort Laramie made the only source of light for Angela Montgomery of Cheyenne just after midnight on Friday.
The moon was absent and the stars brilliant. A gentle breeze kept any bugs at bay.
In her 19th year wearing the red vest and logo of the National Pony Express Association as part of the Goshen and Platte counties chapter, Montgomery said reenacting the history of the storied riders keeps bringing her back.
Half of those rides covering the 80 miles from the Nebraska border to Glendo have been at night, which in Wyoming can be pretty isolating.
The challenge?
“Seeing, just kind of knowing where you are going,” she said.
Facing the night on the 2026 National Pony Express Association re-ride means fewer mosquitoes and flies but more of a chance a horse can mistake a shadow for a hole.
But just like the riders who carried the mail the nearly 2,000 miles from St. Joseph, Missouri, to Sacramento, California, from April 3, 1860, to Nov. 20, 1861, every challenge and obstacle needs to be overcome to deliver the official bag of letters and postcards — called a mochila — on time in 10 days.
This year the east-to-west schedule calls for the mail to arrive in Sacramento around 4:30 p.m. on Thursday. But the mail already was 2 1/2 hours late getting to the border west of Lyman, Nebraska, before Wyoming riders take it 489 miles across the Cowboy State.
Lingle’s Stephanie Goulart, captain for the Platte and Goshen counties chapter, said the Nebraska group had to wait for a long freight train along their route and a rider had a “wreck” that meant a delay to provide assistance and get the mochila on another horse’s back.
Her 11 riders were trying to make up some of the lost time.
“Everybody is riding hard and staging for quick handoffs,” she said.
Goulart and her husband, Tony, rode a 7-mile stretch through an irrigation area that was undergoing reconstruction.
Tony carried the mochila on his horse, Sarah, and wielded a flashlight to help them find their way to the old Fort Laramie Bridge at 1:35 a.m.
Stephanie and Tony Goulart deliver the mail to the old Fort Laramie Bridge handoff site early Friday morning. (Dale Killingbeck, Cowboy State Daily) 
Scott Montgomery loads his wife’s horse. (Dale Killingbeck, Cowboy State Daily) 
A rider gets ready to carry the mail early Friday morning. (Dale Killingbeck, Cowboy State Daily) 
Riders switch the mochila between Lingle and Fort Laramie. (Dale Killingbeck, Cowboy State Daily) 
Stephanie Montgomery heads down a dirt road with the mail between Lingle and Fort Laramie. (Dale Killingbeck, Cowboy State Daily) 
Stephanie and Scott Montgomery trailer their horses to take them from the Lingle area to a Fort Laramie location for the next ride. (Dale Killingbeck, Cowboy State Daily) 
The annual Pony Express re-ride doesn't stop at night, which in Wyoming gets pretty darn dark. “Knowing where you are going,” can be one of the toughest challenges of night riding, say Goshen and Platte county riders who carried the mail Friday. (National Pony Express via Facebook)
Miles In The Saddle
Before their group’s 80 miles was done on Friday morning, Tony was facing 16 miles in the saddle total and Stephanie, 11. It’s their 16th year on the re-ride.
“Our oldest daughter originally started doing it and she had such a great time that we kind of decided to join the year after,” Stephanie said. “We’ve been doing it as a family ever since. We really enjoy re-enacting the history of the Pony Express.”
The assignment for the night riders carries a little more risk.
Stephanie said the association typically tries to schedule the ride to coincide with a full moon.
That didn’t happen this year.
As the horses pass through Wyoming, the moon is waxing toward full on June 29. The moon was gone by the time riders made the old Fort Laramie Bridge early Friday.
When the Pony Express trails coincide with a roadway, vehicles behind the rider typically provide some light.
But for her group, which mostly follows the original trail, the ride off-road included two 7-mile stretches without vehicle support.
Clouds covering the moon make the ride more challenging.
“We’ve had a few incidents over the years where we had some close calls with horses and riders, but thankfully we’ve never had any major wrecks,” she said. “There’s actually been a couple of times where we’ve ridden through some hail, lightning and heavy rain, and we try to keep going as much as we can.”
Goulart said that for the most part, horses are willing to ride at night.
Wyoming’s National Pony Express Association President Les Bennington of Glenrock said that when vehicles follow horses at night on paved and gravel roads the light typically casts shadows that can confuse a horse.
“The horses see those dark shadow and think they are stepping in a hole, so that bothers them,” he said. “If you are in tall weeds, that definitely makes shadows but just being on concrete or pavement that also is pretty tricky.”
In past years, Bennington has seen riders carry their own headlights when they ride and he has also witnessed lights placed on the chests of horses to help both horse and rider navigate the night.
Bennington said that on the prairie with moonlight, horses tend to do better than on the concrete and pavement.
Once participants ride at night they have a better understanding and “feel” for the night-rider role, he said.
Enjoying The Night
Jay Jensen, 75, who rides with the Natrona County chapter of the association, said he enjoys taking the night assignments.
The chapter picks up the mochila across from the Glenrock group at the Sinclair Refinery in Casper and takes it to Jeffrey City.
He planned to do the 3-mile stretch from Devil’s Gate at Martin’s Cove to Cherry Creek Campground late Friday that would also be a solo ride without support vehicles behind.
“I like riding the nights, especially when there is a full moon,” he said. “It’s really gorgeous out there.”
Occasionally, the night ride spooks some pronghorn or deer, but there has not been any issues with his horses.
This year, he has a new horse, Gus, and has been taking him out at night and riding him in the dark to prepare him for the mission.
Jensen said he takes his horses at a slow lope through the darkness.
“We’re on a time schedule,” he said. “We’ve got 59 hours to get through Wyoming.”
Bennington said this year’s ride includes a special commemoration of the nation’s 250th birthday.
“We’ve got a 250th flag that the U.S. Department of Transportation sent us. They want that carried in at least one place in each state,” he said. “We’re going to do that at the National Historic Trail Center.”
The Pony Express schedule this year has plans for a handoff on Main Street in Atlantic City at 8 a.m. Saturday, 2 p.m. at Farson on State Highway 191 and 28 and Uinta/Sweetwater County Line on Granger Road at 6 p.m.
Those time frames will be delayed unless riders through Central Wyoming are able to significantly make up time.
A real-time tracker of horse and rider through the state can be found at the National Pony Express Association website.
Dale Killingbeck can be reached at dale@cowboystatedaily.com.
