I'm in Sunnyvale, so it is somewhat longer for me, but I have gone from my house to Capitola-- an 82mile round trip through town, over the Los Gatos Creek Trail, around Lexington reservoir, and up Old Santa Cruz Hwy to Summit Rd, then down Soquel-San Jose Rd. Depends on how you feel about a little dirt, though (I have a CX bike).
The more common route is to go up and over to Santa Cruz via Highway 9. Then you can go north on 1 and come back up on 84, then come back to Los Gatos via 35 to 9.
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--Ben
2006 Trek SU100, 2009 Motobecane Fantom CX, 2011 Motobecane Fantom Cross Uno, and a Bakfiets
Previously: 2000 Trek 4500 (2000-2003), 2003 Novara Randonee (2003-2006), 2003 Giant Rainier (2003-2008), 2005 Xootr Swift (2005-2007), 2007 Nashbar 1x9 (2007-2011), 2011 Windsor Shetland (2011-2014), 2008 Citizen Folder (2015)
Non-Bike hardware: MX Linux / BunsenLabs Linux / Raspbian / Mac OS 10.6 / Android 7
Last edited by bigbenaugust; 02-07-12 at 05:38 PM.