Tour Rides




The annual Highlander Cycle Tour consists of multiple ride options, ranging in length from as little as 16 to just over 100 miles, and with varying difficulty of climbs. The routes change every year in the Tour de France style/tradition, where we visit different topography along the way. The routes are all designed to share common sections and rest stops so that cyclists on different rides can ride together and have common experiences. Tour routes take riders along lake shores, up hill tops with wide vistas, along scenic valleys, and wander through several small towns and hamlets. The Finger Lakes is a wine growing region and the routes typically go past many vineyards. The Tour is also a charity event with proceeds above expenses donated to charities.

SAG stops are strategically placed and well stocked, often at truly scenic stops or venues (e.g. wineries). Road rides, in addition to detailed maps and cue sheets, are well marked on paved roads with light vehicle traffic and the Mountain bike course has plenty of epic single track (self-guided).

Below are brief descriptions of the Highlander Cycle Tour rides with links to more detail.

Highlander Century and Midlander:    
The Highlander Century and the “Return” of the Midlander route (with Alternate reduced climbing options) for 2023 will tackle routes never used before with visits to Seneca Lake for the first time. The 2023 routes will depart slightly from the norm with an easier collection of climbs and total elevation. The Highlander and Midlander are designed to follow very similar roads and KOM challenges along the way. Rest stops are all the same way points. The Midlander Alternate route eliminates 3 major hills and a few miles. Max grades drop from 12 to 8% on this.  For anyone interested in adding vertical to the Highlander Century, please ping the Ride Director for suggestions. For now though, enjoy the respite, as we plan epic itineraries for our 25th anniversary!

ROAD MARKINGS: Follow yellow chevrons on the roads for Highlander Century and Midlander.  Anywhere that the Midlander diverges, there will be an “M” marked along with the yellow chevrons. The Midlander Alternate will be marked with “ALT” along with the yellow chevrons. The Gravel Grinder course will use orange chevrons where possible. The Lite course will use white chevrons.

We recommend that your rear cluster has at least a 32 tooth sprocket. Compact gear sets work really well given some of the steep ascents (typically that means a 50/34 teeth on front cogs and 11-32 range on rear cluster).

See 2023 Century Map – 2023_Century_Final

2023_Midlander_Map(s) –  2023_Midlander_Final (includes Alt)

Get .gpx or .tcx data here for core Century (100mi/7509′):

Get .gpx or .tcx data here for Midlander (86.5 mi./5797′):

Get .gpx or .tcx data here for Midlander Alternate (81.9 mi./5155′):

CUE Sheets here: We highly suggest having a bike computer or downloaded .gps files to your phone. Some of the area we ride in is poor in cell coverage. If you want though, feel free to print your own copy at links below.


Cues Midlander

Cues Midlander ALT

KOM CHALLENGE: new from 2022 and on, we are partnering with 4 local bike shops to sponsor prizes to the best times up the hills (more $ if it’s a true KOM!). Here are the hills and the STRAVA links which we will use to manage this. It goes without saying that E-Bikes are not allowed. You can click on each link and “Star” the segment so it becomes live on your computer when you hit the hill. Now CLIMB STRONG!!!!

CR33 (Cat. 4 climb) –

Italy Turnpike (Cat. 3 climb) –

Anthony Rd.

Main St. out of Rushville

Highlander GRAVEL 

This will be our 6th year of offering a Gravel option. This route will combine some of the Century roads but diverge onto some epic unpaved/gravel/dirt roads in the area.  It will be approx. 55 miles/5774′. This will include numerous roads near South Hill.  You’ll want to have at least 33 mm wide tires (we recommend 35 or bigger) and 32 teeth or more on the rear cluster. Tune up on your brakes is also recommended. Follow orange chevrons on the road.  

See: 2023_Gravel_Map –  2023_GravelGrinder_Final

Get .gpx or .tcx data here for the Gravel course:  Routes · Ride with GPS

Cue Sheet here:


Highlander Lite
The Lite version of the Highlander will take a kinder/gentler approach with just a few climbs while maximizing the scenic splendor down to Naples, along Canandaigua Lake and back. Total distance of ~ 39 miles/3086′.  Follow white chevrons on the roads. Note: For families with young riders, there are even shorter options of 11 or 16 miles with less climbing, about 400 and 1000 feet respectively. Please see the ride organizers for suggested routes tailored to your own goals.

See:  2023_Lite_Map –  2023_HCT_Lite_Final

Get .gpx or .tcx data here:

Cue sheet here:


For the mountain bike enthusiasts we offer a 40K off-road challenge including climbs up several of the areas 2,000 foot peaks. The ride will NOT BE MARKED and will be self guided.   The course remains essentially the same since 2017 with options for the adventurer at heart. We suggest spending the bulk of your time in the OCP section, trying different color loops. Spectacular riding up there!

UPDATE 2022: The Stid Hill NW section is no longer available due to early hunting season allowances by the DEC. A route around is available as shown here.

See Mountaineer 2017 Course Directions, OCP Detail Map, Camp Cutler Detail MapMountaineer_Overall Map.


The Highlander prides itself on providing a safe, well run, and accommodating event for all participants. The Highlander staff takes the safety of the riders, the spectators, and the communities through which we ride very seriously. To promote this, each rider should have read and follow the NYS DOT cycling guidelines, found here:

Bicycling Safety in New York

If riders do not follow these guidelines, the Highlander may be forced to limit or terminate the ride. Your help and attention to keep the highlander a safe, premium tour is appreciated.

For more good tips on bicycle safety and general rules of the road see here: