Live Entertainment

Various local bands and performers will be preforming at the festival.

Entertainment directors are:

  • Downtown Stage – Terry Britton

Pepper Eating Contest

On Stage downtown At 12 noon
Contact Chris Parsons At “Better Burgers” for contest rules

Antique Tractor & Small Engines Exhibit

Southwest Antique Tractor Association will exhibit antique tractors in the downtown area from 9am-parade time.  All tractor enthusiasts are welcome to participate.

Car & Bike Cruise In

Lonesome Pine Car Club will host a car and bike cruise in, at Subway

Chili Cook-Off

Chili Cook-Off will be hosted by Pennington Gap Fire Department.
Contact Brian Skidmore

Rowlett Road Race (5k)

The Steven Rowlett Memorial Road Race began as an idea between Rick Watson and Steven Rowlett with the two runners agreeing that a race should be included among the activities of the Lee County Tobacco/Fall Festival.
The initial race was held in 1990 with 30 participants braving 27 degree temperatures over a three-mile course. Lee Bank served as the race sponsor that year and has been the sponsor each year since.
Rowlett died the following year in a plane crash with the idea suggested to Watson to rename the race in his memory. The first Steven Rowlett Memorial Road Race was held on October 26, 1991 and has been one of the attractions of the Pennington Gap festival each year.
“Steve had a great love of running and he was such an outstanding leader in the community,” said Watson. “The road race is a tribute to him and the great turnout each year represents the love and respect people had for him.”
The challenging 5,000 meter course has become a benchmark for many area runners for the array of hills that test their endurance.
“We changed our course layout in 1992 when Lee Bank moved to their new location and added a one-mile fun run/walk which has been popular,” explained Watson. “We’re not the fastest course with all the hills in Pennington Gap, but we do pride ourselves on being a friendly and welcoming event with many returning year after year.”
The 25th annual Steven Rowlett Memorial Road Race will be held on Saturday, October 25 with the race start and finish at Lee Bank,
41371 West Morgan Avenue,
Pennington Gap, VA 24277.

For the road race registration form Click HERE

Beauty Pageant

The beauty pageant to be held at Lee Theatre at 5pm on Saturday, October 18th.
Contact Nancy Woliver 276-546-2638
Pre Registar for the Beauty Pagent:
Friday Oct 3rd & Saturday 4th from 4pm-6pm At the Lee Theatre Lobby
Saturday Oct 11 and Sunday Oct 12th at Leeman Field Mobile Home Office From 3 to 5 pm
For the beauty pageant registration form Click HERE


Did you know?
The Lee County Tobacco Festival is an official designated stop on The Crooked Road, Virginia's Heritage Music Trail.