Recap: 20th Annual Gateway to the Cumberlands Jeep® Jamboree


Two weeks ago, we were fortunate enough to be on the ground at the 20th Annual Gateway to the Cumberlands Jeep® Jamboree in Williamsburg, Kentucky. The Cumberland Mountains made a perfect spot to hit the trails. And with over 300 people in attendance, there were quite a few trails to choose from.



The two-day event began early Friday morning in the parking lot of a water park in Williamsburg. As the Jeep brand vehicles filled the parking lot, it was quickly clear that there was a wide range of participants. We saw everything from a restored CJ-5 Renegade and YJs to WKs and JKs.



The participants varied as much as the Jeep brand vehicles did. Attendees ranged from first-timers to individuals who had been on over 45 Jeep Jamborees. It didn’t matter your level of experience. There was a trail for everyone to participate on.



One of the trail guides, Patrick Workman, who has been trail-guiding for nearly 10 years, set off on his first Jeep Jamboree in 1997.


“This is my 48th Jeep Jamboree or so,” said Workman. “Believe it or not, going to Jeep Jamborees was my wife’s idea. We bought a brand-new Grand Cherokee back in 1996. She said she wanted to go on a Jamboree, but I said we weren’t going to take a brand-new Grand Cherokee out there. Well, you know what happened. Our first Jeep Jamboree was back in 1997. Ever since then, we’ve been doing Jeep Jamborees, had a great time, and met a lot of different people.”




You definitely didn’t need to have as much experience as Workman to participate in this Jamboree. Mark Gainer and Doug Sams were both first-timers at the 20th Annual Gateway to the Cumberlands event.


“I’ve had a really good time so far,” said Gainer. “Everything has been really well organized, and from that standpoint, it makes it all very enjoyable.”


“The trail guides are very good,” Sams added. “They know where to place the vehicles and are able to tell people where they need to go to get through. They’re very helpful.”



Workman also spoke about the community created at Jeep Jamboree events.


“It’s been a great experience,” he said. “I’ve met a lot of new people and a lot of new friends. Even some lifelong friends. Some of the guys we’re here with today take vacations together, and go out west. It’s a great opportunity to see the nation and enjoy your vehicle.”


This year’s Gateway to the Cumberlands Jeep Jamboree had people from over 30 states participating. With so much enthusiasm packed into this two-day event, there’s absolutely no doubt that fans of the Jeep brand are the best people around.


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