For the fourth year, Chestertown is bringing back the Roaring 20s. Rum Runners Weekend remembers Prohibition when bootleggers were an important part of local life.

The event kicks off Friday night at 5 pm when Federal Revenue Agents chase a band of bootleggers through local restaurants, starting at The Hub in Brant Lake, and then traveling to the Black Bear in Pottersville, OP Fredericks in Loon Lake, and the Odd Duck and The Bullhouse in Chestertown. At 9 pm, the bootleggers then move to a basement casino featuring blackjack and roulette at The Bullhouse ($25 admission),  while nearby the Panther Mountain Inn is transformed into a Jazz Club.

Tri-Lakes Business Alliance Secretary Cindy Mead says the event started with an ongoing summer antique car show.  “That sparked the idea,” says Mead. “We do a car rally from Landon Hill Rd (CR 68) in Pottersville to Chestertown. It used to be a shortcut for bootleggers operating in the 1920s to get to Route 9.  Now we have a Classic Car parade on Saturday that ends at the Chester Town Hall where the American Legion throws a USO Show.”

All day Saturday events are family friendly. At 11:45 am, a classic car parade will leave Pottersville and end in Chestertown around noon, followed by the USO Show at Chester Town Hall. At 3:30 pm Georgie Wonders Big Band will perform at the Carol Theatre ($20 admission). There will be dinner specials throughout the weekend ($19.25) as well as free carriage rides from Circle B Ranch.

“There will be a Speakeasy at the Panther Mt. Pub on Saturday evening,” says Mead of the vent, which begins at 8 pm. “There are jazz bands and a charleston contest. I am always thrilled by the level of competition. In 2014 we won the Adirondack Park Agency Best Off-Season event. Everyone dresses up. If someone just happened upon Rum Runners Weekend, they would think they went back in time.”

The event takes place this weekend, September 16-18, so grab your flapper dresses, feather headbands and striped gangster suit and head to the Town of Chester. Yes, you will need a password to gain entrance to the Speakeasy. Enjoy!