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“Bare Hill is the legendary birthplace of the Seneca Nation of the Iroquois Confederacy.”

“The name Canandaigua in the Seneca language means The Chosen Spot.”

A Tour Through History

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At the top, the rider is treated to some nice rollers and downhill into Middlesex. It was here that Marcus Whitman, missionary to the western Indians, was born and raised. He and his wife, Narcissa Prentiss were killed while serving in his calling. The local high school that serves the

Rushville-Gorham area was named after him. It is often the site of vigorous cross-country running competitions. You may have noticed as you ascended SR 53 out of Naples, a marker noting the naming of the route after Narcissa.

Vine Valley

Next the rider hops over to the lakeshore once again into a beautiful area known as Vine Valley. But of course nothing is left too easy on this ride and so you must overcome Bare Hill Road to get there. Bare Hill is the legendary birthplace of the Seneca Nation of the Iroquois Confederacy. The legend talks of the killing of a giant serpent by a surviving Indian brave who was accompanied by an Indian maiden. Each year on the Saturday before

Labor Day there is a traditional "Ring of Fire" around Canandaigua Lake that signifies the end of summer. The signal for everyone to light their flares is the lighting of a bonfire on the top of Bare Hill. Tradition has it that this was a carryover from the Senecas. After a refueling and more climbing out of Vine Valley, conjuring images of French vineyards, the rider is treated to a nice respite on the route to Naples.

Last Climb and Canandaigua Vista

With fresh energy in the legs, the riders face the final monster climb of Griesa Hill up to the “High Road,” CR 12. A fitting reward awaits all those who reach the summit. A truly beautiful panorama spreads out in front of you as you pass fields of splendor once home to the luscious grapes of Vine Cliff, set to the backdrop of Canandaigua Lake and the Eastern hills. Our final rest stop now looks over this view and is one of the most photographed points in the Finger Lakes. The final leg runs through the hamlet of Bristol Springs, known for its cold-water springs. One can see some of the

still vibrant signs of days gone by in local merchants shops such as the venerable “Grapery,” home of Arbor Hill Wines, a founding sponsor of the tour and producer of some of the finest grape products on earth. The old town Grange hall still houses town functions as it has since early in the last century. The Highlander is proud to have played a key hand in restoring this turn of the century building with our donations. Just south of the hamlet, less than a mile away, is the site of the last known Seneca wigwam site, last occupied in 1815.

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