Live Entertainment

Marty Stuart – Live at Lee Theatre Saturday, October 24th

Marty Stuart

Bad Habbitz – Live at Lee Theatre Friday, October 23rd, 7pm

For more information concerning entertainment please contact:


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

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 26th annual Steven Rowlett Memorial Road Race will be held on Saturday, October 24 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

Sleepy Hollow Bike Race presented by Moving Forward

The 2nd Annual Friends of the Lee County Tobacco Festival Sleepy Hollow Bike Race presented by Moving Forward Physical Therapy will start at 11:00am on Oct 24th.  Moving Forward Physical Therapy, Inc.’s goal is always to promote wellness in the community. We want to begin a tradition to raise funds for a needed cause in Lee County on an annual basis using cycling to explore the endless beauty of our back roads.  Bike Race will consist 35 mile route with 2400 feet of elevation.   For more information, visit the Cycling for a Cause Sleepy Hollow and click here for a MAP

Beauty Pageant

The beauty pageant to be held at Lee Theatre at 5pm on Saturday, October 10th.
Contact Nancy Woliver 276-546-2638
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.