The Alliance organized Rum Runners Weekend, held in mid-September, where the entire community joins in the festivities to celebrate the Roaring Twenties.
The Town of Chester and others on the direct route from Canada to NYC played a huge role during Prohibition in the 1920’s.
Based on this theme, Jazz Music, Model T’s, Gangsters and Flappers are seen on the streets and in the businesses throughout the weekend, making a visitor wonder if they had walked through a time machine. Local restaurants offer $19.25 specials throughout the weekend with staff dressed for the era. Enjoy Friday Night’s Chase of the Bootleggers at area pubs and trying your hand at gambling at a warehouse casino! Saturday morning offers a car chase over Landon Hill, a notorious boot legging route, with over 25 vintage cars traveling from Pottersville to Chestertown. Saturday afternoon brings Babe Ruth Baseball & Battle of the Bats for young and old, with Georgie Wonder’s Big Band later Saturday afternoon at the Historic Carol Theatre. Saturday night Speak Easy at the Panther Mt. Inn is complete with locked entrance door needing the password to gain entrance, Jazz Bands & Charleston Contests! All ages don costumes of the era throughout the weekend, so join us if you can—and don’t forget your flapper dress!
Schedule of Events
Friday, Sept. 15, 2017
- Vintage Car Rally through Brant Lake (The Hub), Pottersville (Black Bear) & Chestertown (OP Fredericks) in search of the notorious Wesley and his band of bootleggers!
- Casino Night 8PM – $25 admission buys you gambling money for a chance to win some great prizes! Roulette Wheel, Poker Tables, Craps and more!
Saturday, Sept. 16, 2017
- 11 AM: Classic Antique Car Race over Landon Hill – keep an eye out for the shootouts on Main St.!!!!
- 11:30 AM: Babe Ruth Baseball & Carnival for the kids at the Chestertown Municipal Center Rear Field
- 3:30 PM: Georgie Wonders Big Band at the Carol Theatre. Tickets $15 pre-bought or $20 at the door. Call #518-494-5318 to reserve seats.
- Enjoy $19.25 Restaurant Specials throughout town all weekend!
- Evening Speakeasy at the Panther Mt. Pub with Jazz Bands & Charleston Finals
The Rum Runners’ Weekend was honored to be recognized as winner of the 2014 Adirondack Park Excellence Award for Best Community Event (Spring / Fall).