Skyline: 48 miles

Skyline is the benchmark awesome commute in the bay area, with knockout scenery, awesome paths, tough climbs, and fast flats. It's not easy, but not ridiculously hard either. Common sights include herds of deer, misty vistas with pines poking through, drop-dead sun rises, and ideal riding roads. It's also freezing cold in the winter, especially on Sawyer Camp Trail, but you can persevere. Highly recommended.

distance: 48 miles (to Google)
travel time: ~3 hours
elevation gain: ~2,200 feet
difficulty rating (1-10): 7
full-size map
meetup point: peet's coffee, panhandle
turn-by-turn directions
inventor: brett lider, brian wickman

Note that there are many variations of this ride, and you can make it quite a bit shorter/more direct if you want. Some common variations:

Start from Ritual, take Mission south to John Daly, go west to Skyline, and continue like usual (42 miles). This is a nice alternative if you live in the Mission or Bernal and don't want to go north to GGP, only to ride south again.
Portola Loop: If you want more miles, take a right on Sand Hill, which becomes Portola.
Manzanita: From Mountain Home by Woodside Market, turn left onto Manzanita and then rejoin Sand Hill like usual.

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