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Rum Runners' Weekend in Chestertown

  • group of reenactors
  • five reenactors in a line
  • rum runners weekend logo
  • group of reenactors near old vehicle
  • a closed sign on a door
  • group of people dressed up in a room
  • a few classic vehicles
  • old vehicles and reenactors in road
  • fake wanted poster
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Travel back in time with us to the Roaring '20's to celebrate the Prohibition Era on the Bootlegger's Trail! Flappers, jazz music, gangsters and classic cars invade town on this fun filled weekend just 20 minutes north of Lake George!

September 14th & 15th, 2018


  • Feds chase the Bootleggers! Starting at 5PM at The Hub and then traveling to OP Fredericks, Odd Duck & The Bullhouse, ending at the Panther Mt. Pub with Charleston ‘Lessons’ during the evening.


  • 2PM Prohibition Comedy Show at the Carol Theatre to benefit the Adirondack Volunteer Firefighters Benevolent Association.
  • 3PM—5PM Classic Car Show in the center of town
  • 3:30 PM Bootlegger Car Chase w/Classic Cars and Re-enactments of the era!
  • Speakeasy at the Panther Mt. Pub 8PM with Charleston Contests @ 9PM

$19.25 Dinner Specials throughout town all weekend!

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