The ride starts and ends in Sebastopol. The course heads north and east for six flat miles to the city of Santa Rosa and takes the next seven miles to cross the city (usually very quiet at that hour in the morning). At 13 miles, the route becomes rural again, with the first rolling climb out of Bennett Valley. 

The first major challenge arrives at mile 25 with the steep climb of Trinity Road, up and over the ridge between Sonoma and Napa Counties. There will be an informal water stop near the summit. Dry Creek Road, the descent into Napa County off the backside of Trinity, is steep and twisting. Give this nasty section some respect: leave a little margin for error when tackling its steepest pitches. After an easier climb on Oakville Grade, the road tilts downhill dramatically into Napa Valley. It's well-paved and not too technical and can be extremely fast...but those high speeds have led to a number of ugly crashes in past TTs. 

The next 41 miles (36-77) roll easily through the picturesque vineyards and meadows of Napa, Knights, and Alexander Valleys, with only a few moderate hills. The first full rest stop--and time control--is in central Calistoga (mile 55). Serious climbing begins again at Geysers Road, with the next rest stop at the top of the nine mile, twin-summit climb (mile 85).  The midday lunch stop is at the Warm Springs Dam.

After lunch is when the Terrible Two gets truly terrible. The first half of the TT climbs over 7500' in 112 miles. The second half climbs over 9500' in under 90 miles, 5000' of it in the first 30 miles after lunch. It often takes riders up to three hours longer to complete the second century...if they finish it at all. Skaggs Springs—the road the Army Corps of Engineers built to bypass Lake Sonoma in 1981—is an endless series of steep, sun-baked climbs and false summits. It can be very hot (90°-115°). There will be two informal water stops along this stretch. Eventually, the old road emerges from under the lake and the course returns to pavement from an earlier age...bumpier, but also shadier. After 15 miles of steep ups and downs, riders can recuperate on 12 mellow miles of downhills and rollers along the beautiful Gualala River.

The next full rest stop is at Kashia School (Rancheria) at mile 144. There is a notorious climb leading up to this rest stop: a wicked, 1.7-mile, 900' wall. After the stop, there is a steep, technical descent to another fork of the Gualala River, an easier 300' climb, then another tricky drop to the sea. At Stewarts Point, the route turns south along the ocean on Hwy 1. Temperatures are usually much cooler here and sometimes one can even catch a tailwind while cruising for 15 miles alongside the rugged coves and pounding surf. Although this Hwy 1 section is considered easy, it actually adds nearly 1000' of climb to the total before reaching the next rest stop at Fort Ross (mile 164).

The climb on Fort Ross Road—after the rest stop—is 2.6 miles, averages 11%, and feels even steeper. Some riders find it to be the hardest climb of the whole ride. However, most of it is shady and all of it is beautiful. It’s followed by a bumpy, narrow descent, a more gradual climb to the Black Mountain summit, and a long, technical descent to the village of Cazadero. A flat, shady run down Cazadero Hwy and along the Russian River leads to the last rest stop in Monte Rio (mile 185). After that, the road climbs gradually along Dutch Bill Creek for seven miles, just skirting Occidental, before a long, smooth, fast downhill into the Green Valley, north of Sebastopol. After the long roll-out at the base of the descent, there is one more small climb on Graton Road and then, just over the top, the right turn onto Sullivan and the route back to the start These last miles include a few more small climbs and moderate descents. 

Except for the 7-mile transit of Santa Rosa and a brief visit to Calistoga, the entire course is rural and very scenic: vineyards, orchards, pastures, oak-studded meadows, shady forests of redwood, bay, and madrone, the spectacular coastline, wild rivers, lakes and streams, and always the sweeping panoramas from the summits of all those climbs. It’s enough to make you forget how hard it is! It is of course very challenging but it is never dull.

The ride will be held, rain or shine. (Yes, it has rained on the TT, although very rarely.) Temperatures can range from 50° in the morning to well over 100° in the afternoon on some of the inland portions. It will cool down again as riders reach the coast and encounter fog or its influence. The wind can be a factor, but is not usually a major player in this hilly terrain.