Difficulty: 4 stars (out of 5)

Number of riders: 6-10

Stops: 3

Length of day: 8-10hrs

As the name suggests, this route offers roughly 77 miles and 7,000 feet of riding on some of the finest roads in Northern California. Starting and finishing near the town of Occidental, you will traverse through the towns of Monte Rio and Guerneville before heading up to Sweetwater Road, which is a beautiful, meandering climb with some steep grades. You will then drop back to Guerneville before heading to Cazadero and Fort Ross Road, which climbs up and over to the coast. From there, there’s a rippin’ descent to Jenner, where you have the option of either climbing Willow Creek (gravel) or Coleman Valley Road up and over to our endpoint back in Occidental.

Difficulty: 5 Stars

Number of riders: 6-10

Stops: 3-4

Length of day: 10-12hrs

This route, starting and finishing in the town of Healdsburg, heads out in a westerly direction along wonderful winding vineyard roads before tackling the first of three challenging climbs. Sweetwater Road needs to be ridden to be understood; with its steep pitches and tight turns on the descent, it takes all of your skill to master this mini monster. From there, you pass through Guerneville and head up through Cazadero for Kings Ridge Road, another iconic California climb. After you’ve checked that box, you make your way over to Skaggs Road. From there, you’re pretty much in the woods all the way to Lake Sonoma before bombing back down to Healdsburg for what can only be described as a badass day on the bike.

Difficulty: 4 Stars

Number of riders: 6-10

Stops: 3-4

Length of day: 10-12hrs

Who knew there were roads beyond Sonoma? We did! This loop, starting and finishing in the quaint town of Lakeport, is not for the faint of heart. With a willingness to try something new, you’ll need an appropriate bike, ideally with 30mm-32mm tires, as we hit some dirt roads. We can start from either Lakeport or Holland, depending on where we drive in from, but regardless, you are in for a massive day filled with mind-blowing dirt fire roads, sweeping descents, open roads void of traffic, and views for miles.

Difficulty: 4 Stars

Number of riders: 6-10

Stops: 3

Length of day: 8-10hrs

Deep in the redwoods north of Petaluma lies the small town of Occidental. From there, you will ride up through Cazadero to the beginning of Kings Ridge. Then, we climb all the way over to Skaggs and back past Lake Sonoma to Cloverdale. After a quick stop to refuel, you tackle the Geysers, which start off with a meandering, broken paved road that turns into a hellish couple of climbs, eventually dropping you out near the town of Jimtown. From there, it’s a flat run into the town of Healdsburg to the finish. You’ll be rewarded with a quaint town full of food and wine options and also a river to jump into if desired.

Difficulty: 5 Stars

Number of riders: 6-10

Stops: 4-5

Length of Day: 10-12 hrs.

Starting from the town square, we will ride north for a few miles to warm up before the first climb of the day. Cavedale Road, a winding, partially paved road, will bring you up and over to Trinity Grade and then down a fast descent to Oakville. From there, we head to Rutherford to refuel before continuing on to Lake Berryessa via Highway 128. Heading lakeside north, we cut in on Pope Canyon Road to Pope Valley and then head north again to Highway 29. From there, we take Big Canyon Road over to Middletown and then tackle the second big climb of the day: Western Mine Road over to Kellogg and back to Healdsburg. This is one tough day and should only be attempted on cooler days to avoid dehydration and heatstroke.