The furry creatures will be judged in the two traditional categories: cutest and cuddliest and biggest and woolliest.
Some believe the woolly bear's two black stripes, separated by a brown stripe, can foretell how much snow we'll be shoveling.
Legend has it that the wider the first black band, the more severe the early part of the winter will be, and the wider the second black band, the more severe the latter half of the winter will be.
"It'll be interesting to see what the woolly bear says. The woolly bear did a great job last year," said Gerald W. Spessard, business manager of the Hagers-town Town and Country Almanack.
The back ends of last year's woolly bears had the smallest black bands that Frank Leiter had ever seen in his 14 years of judging.
"It was right and a lot of the weathermen were wrong," said Leiter, 77.
A record-number of more than 1,000 caterpillars were entered in that contest.
Beauty is in the eye of the caterpillar holder.
Leiter said he knows right away which woolly bears have a chance at the crown.
The entrants arrive in all kinds of containers: jars with holes poked in the lids, shoe boxes and aquariums, Spessard said.
Some people build elaborate cages to house the furry creatures, he said.
They are transferred to another container and tagged for Leiter to inspect twice a week.
The ones that don't make the cut are released back to the wild on a farm near Downsville.
Leiter keeps the top candidates in his garage until the contest is over.
The owners of the top winners in each of the two categories will receive $100. Runners-up in each category will receive six free copies of the 1998 almanac.