Jeep Jamboree gearing up for annual trek in Williambsurg

Jeep Jamboree's Gateway to the Cumberlands sees hundreds flock to Williamsburg each year. This year's event will take place this Thursday and Friday. | File photo

WILLIAMSBURG - Jeep drivers and enthusiasts have already begun their annual voyage to Williamsburg, as the city will host the 28th Gateway to the Cumberlands Jeep Jamboree this Thursday and Friday.

“Everything’s a go right now,” Alvin Sharpe told the Williamsburg City Council Monday evening, referencing the yearly event that sees hundreds flock to Williamsburg to take advantage of its unique trails and hospitality. Sharpe said 522 people had signed up for this year’s event, and that he was expecting around 275 Jeeps.

For nearly three decades Williamsburg and its neighboring forests have welcomed those thrill seekers looking to take on trails such as Heaven’s Gate, Commando, Rock Bottom, Area 51 and more.

“The trails on the Gateway to the Cumberlands Jeep Jamboree offer many spectacular views of waterfalls, cliff-lines and rivers,” reads an excerpt from Jeep Jamboree in the event’s itinerary. “In the mornings you may see low-hanging clouds that skim the tops of the mountains.”

Jeep Jamboree also rates each trail on a scale of 1-10, with 10 being the most difficult. It says ratings are based on the overall trail and not just one or two tough obstacles. Jeep Jamboree has rated the trails found on the Gateway to the Cumberlands from as low as 3 to as high as 9.

Those rated 3-5 are meant to be moderately demanding and a challenge to novice drivers. Obstacles may include mud holes, boulders and streams. Those trails rated 8-9 are deemed very demanding and officials say the likelihood of getting stuck is high. A full list of trails and a brief description is provided to all those who sign up, and guides will be on-hand should anyone get lost while on the trail.

“It’s unbelievable the number of people that come in and bring Jeeps and never had it in four-wheel drive,” noted Sharpe. “So, it’s an experience for them. But we’ve got good guides, excellent guides.”

“A lot of people are on a first name basis with our guides,” added Mayor Roddy Harrison. “It’s just a really cool thing.”

Sharpe said event officials and volunteers had been busy at work over the past month and half working on surveying and marking the trails.

“We’re going to have to find more land out there for one thing,” Sharpe added. “Some of these, let’s say, beginner trails are not beginners anymore,” he said drawing a laugh from members of the council. “They’ve increased their difficulty.”

This year’s event is scheduled to begin this Thursday evening with vehicle evaluations, registration and trail selection/sign-ups tabbed to take place at the Hal Rogers Family Entertainment Center (Kentucky Splash Waterpark) from 5 p.m. - 7 p.m.

Over the course of the next two days, participants will be required to attend a mandatory general attendance meeting at the waterpark from 8:30 a.m. - 9 a.m. Trail riding will immediately follow until 5 p.m. Sharpe said he had procured help from different teams at Williamsburg High School, who have offered to provide free Jeep washes to event goers Friday and Saturday evenings from 5 p.m. - 7 p.m. at the waterpark (donations are appreciated). Sharpe said students have also volunteered to help serve during the event’s dinners, which will be held at the waterpark underneath tents Friday and Saturday from 5:30 p.m. - 7:30 p.m.

“I know losing Oral [Lewis] was a big shock to all of us,” said Sharpe. Lewis, a Williamsburg-based businessman who had helped cater the event in the past, recently passed away. Sharpe said the event’s organizers were able to procure David’s Steakhouse for the event’s meals.

“We’ve had to hustle quite a bit to get everything put back together,” he said on the efforts of organizers who help plan an event that leaves a lasting positive impression of Williamsburg on those who attend.

“They love Williamsburg,” he said on those who attend Jeep Jamboree. “I mean you can get on Facebook and look at the compliments we’re getting, it’s unbelievable.”

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