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Terrible Two Course Description

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The Terrible Two course was updated in 2016 after new Napa County special event permit requirements went into effect and we decided to reconfigure the early miles to stay out of Napa County. In spite of replacing the big climb over Trinity with smaller climbs—and in spite of the new course having less elevation gain than the old course— the new course takes slightly longer to complete than the old course.

The ride begins and ends at Analy High School in Sebastopol. It heads west and south from town through the hills and down into the rolling dairy lands around Bloomfield and Two Rock. The route is out into the country in about two miles, with the first substantial climbing challenge beginning at mile 3: up and over the stair-step climbs of Burnside Road and down the south side of the ridge to the hamlet of Bloomfield. 

Once that long descent peters out, the course enters a section of nearly 20 miles of mostly flat and rolling terrain—with only one moderate climb—heading south to Two Rock, then east across the llano of the Laguna de Santa Rosa to the next big climb.

The next big climbing challenge is two-summit Pressley Road. Over the top of the second summit, the route rolls downhill for two miles to the six-mile moderate climb and smooth, fast descent along Bennett Valley Road. A water stop will be located near the Sonoma Mountain Road-Bennett Valley Road junction, around mile 34.

A few miles of lumpy rollers and one modest climb on Lawndale Road follow. All these miles are on quiet roads through pretty woods in the foothills at the north end of the Valley of the Moon. That brings the route to a fast run west toward Santa Rosa on the smooth, wide shoulder of Hwy 12. Although the highway is fairly busy, the shoulders are huge—usually more than eight feet—so the traffic should be only a minor irritant.

The highway leads to a 3-mile cruise through the quiet suburbs around the NE corner of Santa Rosa. There are several stoplights getting into and through the city, but all default to green in our direction, so the odds are good there won’t be too many delays. We’ll have our first full rest stop at a school in the city at mile 51.

After a moderate, pretty climb along Riebli Road, the route zips downhill to another bit of suburbia: two miles through the Larkfield neighborhood. Once beyond that residential fringe, the route stays rural for its remaining 140 miles.

Those rural miles begin with Faught Road and Chalk Hill Road: many vineyards, a fair amount of broadleaf forest, and a few horse ranches, with minimal traffic…all good cycling country. There are three more modest climbs along Chalk Hill that add to the overall challenge of the day. At the far end of Chalk Hill (mile 69), the route joins Hwy 128 just as it begins to descend into Alexander Valley.

After the pleasant, rolling run through the premium vineyards of Alexander Valley, serious climbing begins again at Geysers Road, with the next rest stop at the top of the 9-mile, triple-summit climb (mile 84). The descent off the backside of Geysers begins with an extremely steep drop of about one mile. Following a hard left turn at a junction, it settles into seven miles of gradual downhill into rugged Sulfur Creek Canyon, then several miles of small climbs and longer descents along the canyon. This is an active geothermal area, with steep, unstable terrain. The road is often washed out or in some state of disrepair. There are several sheer drop-offs into the deep canyon, with no guard rails. Caution is advised. After skirting around the edge of the town of Cloverdale, a short climb on Dutcher Creek and a descent into Dry Creek Valley—more vineyards—lead into the midway lunch stop at the Warm Springs Dam Visitor Center (mile 111).

After lunch is when the Terrible Two gets truly terrible. The first half of the TT climbs over 7500' in 111 miles. The second half climbs over 9000' 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, ten miles apart. 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 143. 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 162).

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 along Austin Creek and the Russian River leads to the last rest stop in Monte Rio (mile 184). After that, the road climbs gradually along Dutch Bill Creek for seven miles, just skirting Occidental, before a long, smooth, fast downhill. 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 Analy High School. These last miles include a few more small climbs and moderate descents. 

Except for the 3-mile transit of Santa Rosa and the 2-mile run through Larkfield, 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.

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