The Lee County Tobacco Festival fills downtown Pennington Gap on Saturday, October 24. The weekend opens the night before, when country comedian Cledus T. Judd plays Lee Theatre on Friday, October 23, at 7 p.m.
The festival dates to 1949 and is held on the fourth Saturday of October, according to its organizers, the nonprofit Friends of the Tobacco Festival. They call it the longest-running tobacco festival in Virginia and Lee County’s oldest annual parade.
Saturday’s schedule
These times come from the festival’s website as of October 19.
- 8:30 a.m. One-mile fun run
- 9 a.m. Lee County Heritage 5K road race
- 10 a.m. Butch Williams on stage
- 10:45 a.m. Checkered Past
- 11:15 a.m. Milkshake (ages 6 to 13) and pie-eating (ages 14 and up) contests
- Noon Zach Wiles and Jacob Sturgill
- 1 p.m. Country Cabin Line Dancers
- 1:45 p.m. Huff & Co. live music
- 3 p.m. Parade, from Pennington Middle School to Lee Bank
- 7 p.m. Lee Haw Comedy Show at Lee Theatre
Where things are, and which roads close
Crafters line Main Street. Food vendors and the stage are in the Pennington Pharmacy parking lot, and the bounce houses are behind the Verizon building, the organizers say.
Drivers should plan around the closures. During the festival, Morgan Avenue (the East/West Alternate 58-421 route through town), South Kentucky Street and Main Street are closed. The organizers do not list exact closing and reopening times.
If you are in the parade
Entries meet in the Pennington Middle School parking lot. Floats that want to be judged must be in line by 2 p.m.
The parade entry form sets a few rules:
- Entry is free, except for political candidates, who pay $25 per candidate per car or float.
- Candy may be handed out but not thrown from floats.
- No amplifiers or loudspeakers on floats.
- ATV, UTV and dirt bike riders must wear a helmet and follow traffic rules.
The 5K and the Friday show
Both races start at Pennington Middle School, 121 Bobcat Circle. The 2026 entry form lists a $15 fee for all participants and promises shirts to registered walkers and runners, with the first 100 guaranteed a shirt on race day. Awards go to the top male and female finishers overall, the top masters runners age 40 and up, and the top three in each age group. The form’s information line is 276-546-1210.
The Friday show is sponsored by Friends of the Tobacco Festival, according to the Town of Pennington Gap’s event page, which lists it from 7 to 9 p.m. The town’s online presale page showed tickets at $15.90 on October 19, with the final total calculated at checkout.
A festival for a crop that is still grown here
The festival began as a celebration of the tobacco harvest, and Lee County farmers still grow the crop. In the U.S. Department of Agriculture’s most recent Census of Agriculture county profile, from 2022, tobacco ranks third among the county’s crops by acreage, behind hay and corn for grain. The census withholds the exact acreage and sales “to avoid disclosing data for individual operations.”
Lee County ranked 17th in tobacco sales among the 25 Virginia counties that produced it in 2022. Five years earlier, the 2017 profile put the county’s tobacco sales at $386,000. Farming overall has shrunk. The county had 629 farms in 2022, down from 830 in 2017.
The county is backing the weekend too. At its September 15 meeting, the Board of Supervisors voted to renew its $300 featured sponsorship of the festival, according to the county’s audio recording. Questions about the festival go to the organizers at (276) 346-7836.