HIGHLANDER CYCLE TOUR HISTORY
Brought to you by the Highlander staff and the South Bristol Historical Society

Inaugurated on September 16, 2000, the Highlander Cycle Tour is centered on the Bristol Highlands, above the western shore of picturesque Canandaigua Lake in New York’s famous Finger Lakes Wine Country.

The ride showcases the beauty, the tastes, and especially the challenge of the region and does so in varying degrees of difficulty. The marquee course bears the name of the event…The Highlander Century! The Highlander is considered by many to be among the most beautiful and difficult rides in the country. It now includes 20 significant climbs, totaling ~ 11,000’ of vertical gain, on grades up to 23%! It is a rollercoaster of climbing and known to punish the quads and the unexpecting rider.

Along with the Highlander Century the Tour offers 4 alternate courses of varying lengths and grades all within the same awe-inspiring backdrop of the Finger Lakes wine country.  Most of the courses pass multiple lake shores and ski resorts as they meander around the area. In 2002, the tour added the venerable Mountaineer. It’s without a doubt, serious fat-tire, quad-pounding pleasure for the off-road enthusiast. Covering every major peak in the town of South Bristol, this ride is a fun-loving sister of the Highlander. Estimated elevation gain is in the 7000’ range with climbs of Stid Hill, Gannett Hill and the old' Finger Lakes trail overlook, Camp Cutler, past the old Grist Mill at Boswell’s Corners, and back over and down Bristol Mountain from the backside. The Mountaineer is an extreme ride for the epic adventure seeker.

On a historic Friday evening, Sept. 9, 2004, the Highlander Tour added the Mountain Prologue Time Trial. Five miles and 1,100 ft. of climb up the infamous Gannett Hill with grades of 15% over its 2 miles of length. Truly an epic way to kick off the event and testament to the Highlander’s reputation of bringing the ‘A’ game. Now a weekend long festival of cycling and sport, the Highlander has become a destination and highlight event for hundreds of riders across the country and even as far away as Ireland and Austria! The Highlander has also donated over $50,000 to charity because of the generosity of our rider base. This is all done without requirements to raise pledge money.

From a historical perspective, the tour winds its way through a snapshot of early American history. The tour starts alongside historic Mud Creek, at Bristol Mountain Ski Resort, in the shadow of 2,140’ high Worden Hill and Stid Hill at 2,070’. The tour’s course begins its passage south and west past the first settler’s home in what was called Brown Stand. Gamaliel Wilder, South Bristol’s founding pioneer, came here from Hartland, Connecticut in 1789. He made his way up the Mohawk River, and Canandaigua Lake Outlet to Canandaigua Lake’s Seneca Point. In a relatively short period of time, his small band forged a road west to Brown Stand where he built his first log cabin home. In 1791, Mr. Wilder’s band erected the region’s first Grist Mill at Boswell’s Corner, which marks the base of the first of the major climbs. Nicknamed “Feed Zone Hill,” this section of County Road 33 has seen many thrilling mountaintop finishes in local cycling races. After meandering through Burby Hollow, and climbing up and over the steep Mosher Road, the riders find themselves soon faced with a marvelous, long ascent of nearly 2 miles up Egypt Road before descending to Bristol Center at speeds known to approach 60mph. Here the riders can treat themselves to an old-fashioned country store or continue on, and again up, a perfect climb on County Road 32. The course then turns and heads for the small town of Cheshire with a stop at a century-plus-old general merchandise store called The Company Store. Once refreshed, the Highlander then heads directly for Canandaigua Lake, via a thrilling descent on Duell road.  Turning South onto West Lake Road, the riders can enjoy the emergence of the lake, a resort and summer destination, with beautiful homes and boathouses lining the lakeshore.  Next comes the climb of Miller’s Hill. This climb once challenged the ranks of cycling pros in the now forgotten Canandaigua Cup. At over 1 mile at 10-12% grade, this too is nearly as perfect a climb as can be found. At the top, the course turns toward the fabulous Bristol Harbour Golf Resort, one of the hallmark rest stops of the tour. Here the riders are treated to assorted refreshments, and a beautiful view of Canandaigua Lake. Just below the resort lies famous Seneca Point. Being a distiller by trade, Gamaliel Wilder was drawn here to the Indian’s apple and peach orchards above the point. A hundred plus years later the point became a summer retreat for families out of New York City.  Future celebrities Humphrey Bogart and Catherine Hepburn spent youthful summers here on the lake.

From Bristol Harbour, veterans of the Highlander know what lays ahead, a descent to the lakeshore, again at speeds exceeding 50 mph, and on to Miller’s Landing.  This brings the Highlander rider to the foot of the unbelievably steep Bopple Hill. Bopple Hill is the Highlander’s version of the famous Le Alpe d’Huez from the Tour de France. Bopple reaches a 22% grade at one point and has been known to reduce the rider to walking. First built in 1935, the road is a true test of strength, a badge of courage to all who attempt it, and a medal of honor to those that conquer it. There is a cemetery at the top dating into the 1800’s, made famous in the movie, The Lady in White, which makes for a fitting backdrop. It is rumored that bagpipes can still be heard in this part of the Bristol Highlands. Those that attempt this course will find a reward on this hill with their name sprayed on the road ala Tour de France style. A fitting tribute.

Immediately following is the 2-mile long climb of Gannett Hill, Gannett stands at 2,256’ the tallest peak in the region, a relentless 15% grade nearly the whole way. As a footnote, Frank Gannett, newspaper businessman who owned several newspapers in the Northeast United States, was born just to the south of Ontario County Park. The riders pass this spot as they head south. Frank’s legacy is the Gannett Group, which publishes USA Today. The property here was donated to the U of R by the Gannett family, and is the home of Mees Observatory. A little further down the valley you’ll pass Powell Hill Road. Powell Hill is named after Shotwell Powell, abolitionist legislator and inventor, who settled on land at the south end of the Gannett Hill Road.

Meandering down through Wind Ridge and West Hollow Rd. into Naples, the riders can enjoy passage through this turn-of-the-century town. The settlers of Naples first entered the valley by crossing on the winter ice of Canandaigua Lake. Naples also claims to being home to the first automobile invented in the United States. One of its most famous natives was Marion Clark, a nineteenth century abolitionist governor of New York State. His daughter was Mrs. F. F. Thompson, who owned the estate at Sonnenberg Gardens in Canandaigua, and extensively donated to the community, including donations for the founding of F. F. Thompson Memorial Hospital.

Of course what comes down must go back up in Highlander minds and so the rider quickly encounters a steep climb up CR36 to another well-placed rest stop at the foot of the next climb (French Hill).  Here you will cross paths with Lowlander Century riders coming down the Honeoye Lake Valley.  In 1779, a Seneca village at Honeoye was destroyed by the expeditionary force under the command of General John Sullivan. Interestingly enough, Canandaigua was also the site of another Indian village destroyed by Sullivan’s troops. Today you can see why the area was coveted and fought over. The name, Canandaigua means “The Chosen Spot”.

The next several miles are filled with nice passage among forests of pines and streams, followed by a long climb up SR53. As the route heads south, we are reminded of The Wilder family in South Bristol, who formed the first religious society in the Phelps-Gorham Purchase. The purchase comprised the land running approximately from the Genesee River to Geneva, and from Lake Ontario to the Pennsylvania state line.

Once reaching the apex, the rider is treated to a sweet descent down Prattsburg Road into Italy Valley. A welcome refueling stop can be found here at a Mom & Pop style convenience store. For the extremely courageous, there are extra bragging points available for climbing the hill next door (Italy Turnpike). But don’t forget to come back down. You may want to think twice though. Only the veterans know what is about to hit them next up the valley road. After a nice cruise though Europe-like scenery, a sharp left takes the rider up the incomparable Sliter Road. Peaking at 23% grade and nearly 1 mile long, the climb is nearly unbelievable to the screaming legs and arms. Only the strong and proud will conquer this climb.

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.

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 along the lake shore and more climbing out of Vine Valley, conjuring images of French vineyards, the rider is treated to a nice respite before the final assault back to the base lodge begins. Along the way you might imagine the faint whispers of  Indian villages located at Vine Valley, Naples, and at the Tour’s crossing a few miles south of Middlesex on West River.

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.

All tours finish at Bristol Mountain Ski Resort, which brings a national class appeal to the event with the mountainous backdrops, great food (including Grape Pies from the local area), drink and music to unwind with.

If you have anything left in the legs, in 2006, the Highlander offers our newest challenge. In partnering with the newly reborn Rochester Marathon, the Highathlon has been born. Finish the Highlander Century and the Rochester Marathon and receive a custom award. If you are the fastest Marathoner (M/F), you’ll receive a very nice grand prize! What can we say, it’s the ultimate duathlon and a fitting way to end the Highlander Tour weekend!

Finally, the Highlander proceeds go to supporting the South Bristol Historical Society (preservation of American history), The Lance Armstrong Foundation (cancer), the Rochester XC Ski Foundation, Mercy Flight and other local health and fitness oriented groups.  Our way of giving back to the community that has helped so many.