25th Annual Gateway to the Cumberlands Jeep Jamboree largest one ever
This week’s 25th Annual Gateway to the Cumberlands Jeep Jamboree will be record setting with 306 Jeeps pre-registered and about 500 participants expected to attend from over 20 states.

Hundreds of Jeeps like this one will roll into Williamsburg this week for the Gateway to the Cumberlands Jeep Jamboree.
“This is the largest one I have ever seen. This is the largest that I am aware of in the 27 years I have been with Jeep Jamboree,” said Kentucky Coordinator Don Ford.
“I contribute most of that to the area. They have a saying in Williamsburg that ‘it feels like home,’ and I think everybody with Jeep Jamboree that visits feels that warmth.”
Williamsburg Tourism Director Alvin Sharpe said that he has had a goal the past two years for the jamboree to reach the 300 Jeep threshold, and last year’s event came up just two Jeeps short.
Sharpe said he thinks the area’s hospitality is part of what keeps bringing people back.
“We do things differently here in Williamsburg than in any other place. They leave here with good feelings. They have good trails. The hospitality is something else. It is the only place I know of that gives them a police escort out to the trails in the morning. When you see Jeeps going by Walmart that line going towards Jellico is over a mile long. It is something to see.”
Jeep Jamboree USA is an organization out of California that conducts jamborees all over the United States.
“You have to have a Jeep to be able to get involved in it. You can’t go out there in just any four-wheel drive. It has to be a Jeep,” Sharpe noted. “Really, basically it is a lot of these people who have Grand Cherokees, Wranglers, and so forth that have probably never had them in four-wheel drive. This gives them the opportunity to come here. We have trails from the novice all the way up to the extreme trails for the advanced.”
92 percent of all Jeep Jamboree participants will attend with a Jeep Wrangler, according to Jeep Jamboree USA.
Started 25 years ago
The Gateway to the Cumberlands Jeep Jamboree started in 1994. For the first four years, it was held at Cumberland Falls, but quickly outgrew that venue.
Ford said that one Saturday after all the riders had left out for the trails, he took a drive in his Jeep looking for somewhere to expand.
“I took a little drive and it was like my Jeep had sonar in it. It took me right straight to the Williamsburg Tourism Center,” Ford noted.
Sharpe happened to be in the lobby that morning standing there to great him.
“I talked to him and he didn’t know the meaning of the word no. It was, ‘Yes I can. Yes I can. Yes I can.’ I called the office in California and our founder, Mark Smith, who passed away a few of years ago, made a special trip to Williamsburg,” Ford noted.
After meeting with Sharpe, they quickly decided to move the event to Williamsburg, which hosted its first Gateway to the Cumberlands Jeep Jamboree in 1998. It has been here ever since.
Sharpe admits that it was a stroke of luck that Ford walked in that day.
“We have been good friends ever since,” he added.
Economic impact
“It is going to be a big event for us again. The economic impact is getting bigger and bigger for us. I guess it is one of the bigger events that we have from a standpoint of economic impact in Williamsburg. All the motel rooms are full,” Sharpe said.
In addition to motel rooms filling up, the event is also an economic boost to local businesses, and some local sports teams.
Millys on Main will be providing sack lunches for participants on Friday and Saturday. Oral Lewis will be catering the dinner each of those nights.
The University of the Cumberlands Softball Team will be doing the Jeep washes Friday and Saturday evening. The University of the Cumberlands Cheerleaders will be helping with serving food and handing out gifts and so forth each evening.
“The last two or three years, we have done an economic impact study – each participant fills out a survey – and it has been over $120,000 for the three days. This is including the meals, hotel rooms, and everything. That is pretty good for a small little community,” Sharpe said.
The itinerary
Jeep inspections will take place Thursday afternoon and evening at the Kentucky Splash Waterpark. Registration will then take place at the Williamsburg Tourism and Convention Center where a barbeque will take place that is catered by Sonny’s BBQ out of Corbin.
Friday and Saturday mornings, participants will assemble in the Kentucky Splash parking lot, and will leave out at 9 a.m. to hit the trails, which are located in southeastern Kentucky and northern Tennessee.
This year there are 20 trails.
“With the college helping us out being able to use their property, it has been a great help. We have been able to utilize another 8,000 or 9,000 acres up there that gives us three more trails up there,” Sharpe said.
“I think everybody is going to have a good time. We have some nice little gifts to give to each one of them,” Sharpe said.
This year, shirts have been made for participants commemorating the 25th anniversary of the event. Local artist Josh Bunch designed the logo, and has donated a couple of signed prints that will be given away as a door prizes for participants.
Ford noted that the event wouldn’t be possible if not for the help of the 40 or so volunteers, who work off and on all summer in an effort to keep the trails clear and free of debris.