Live Entertainment

KY Head Hunters- Live at Lee Theatre Saturday, October 22nd



Taylor Ray Holbrook to Open at 6PM



Tickets go on sale at Pennington Gap Town Hall on Sept. 12th  Call to  order 276-546-1177 to purchase with credit card

assigned seats. $25.00 Main Floor    $20.00 Balcony

For more information concerning entertainment please contact:


Pepper – Marshmallow Eating Contest 


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

No entry fees. $50.00 prize money on Pepper eating

Marshmallow Contest for Ages 5-12

$10.00 $15.00 $25.00 prize money for Marshmallow


David L. Browning – The Mayberry Deputy


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

Car and bike cruise in located downtown

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 27th annual Steven Rowlett Memorial Road Race will be held on Saturday, October 22 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

Moving Forward Physical Therapy, Inc. presents 3rd Annual Tour de Sleepy Hollow Bike Ride

Bike Ride will consist of 37 mile long route, 22 mile intermediate route, and 10 mile short route. No ear buds during the event, bike must be in good/safe riding condition, and helmets are required. This is an open course event.
There will be timed segments (Strava App - on the long route only. The best times of the segments will be awarded.

Entry Fee will be $20

Participants will receive T-Shirt and water bottle.

Moving Forward Physical Therapy, Inc.’s goal is always to promote wellness in the community. This will be our 3rd annual bike ride to raise funds for julietta casino online a much needed cause in Lee County. This year’s cause will be to raise funds for a Lee High School senior and a Thomas Walker High School senior to assist with their battle with cancer.

Our facebook page is ….

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 6pm on Saturday, October 8th.
Contact Nancy Woliver 276-546-2638
For the beauty pageant registration form Click HERE

Entry Forms may be dropped off at Pullin Ink in Pennington Gap

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