The Hammondsport-Penn Yan Race was an annual event started in 1927 and continuing through the twenties and thirties, ending about the time of World War II. 

The race served as a culmination of the traditional rivalry between the two towns located at opposite points of Keuka Lake in the Finger Lakes of New York. 

Hammondsport, of winery fame, was the grape producer.  Penn Yan was more grain-oriented and the shipping out point of all lake products including Hammondsport’s grapes.  
Hammondsport boasted Glenn H. Curtiss of bicycle, aviation and boating fame.  Penn Yan had Penn Yan Boats.  Traditionally Curtiss designed and built the Hammondsport entry and Penn Yan Boats would provide a factory racer.  This was a fiercely competitive race that entitled the victor to “bragging rights” for one year.  The trophy was passed between towns and resided for the year in a place of honor in the victor’s domain.

As the Hammondsport-Penn Yan Race is so much a part of the rich history of the Keuka Lake area, particularly our boating history which boasts Penn Yan Boats, Ben Reno and other pulling and fishing boats,

Wine Country Classic Boats revitalized the race in 1984 as an exciting annual event that gives added meaning to the boat show weekend.

 By sponsoring this race and having participants from all over the US, the group feels that they are perpetuating an  important piece of boating history.

While the 1984 race lacked the inter-village rivalry, it did serve to restart a unique event that continues today.  That race was held in wind, heavy rain and rough water, but it only took 30 minutes for Carol and Stanley Shaffer to complete the 19 mile course in their 1963 Chris Craft Holiday.

Over the last 26 years many boat owners have relived the excitement of those original races in the 1920’s.

 Some owners have built boats just for the race.  Others have brought their vintage race boats, and others just ran their stock classics.

 The race has seen its share of break downs and sinkings, but each year the racers return for the fun and thrill of opening the throttle and crossing the finish line.

 The prizes of local wine might also help bring boaters back year after year.