I’ve only done it once, but it was a blast!. San Francisco’s Critical Mass begins at 5:30 on Justin Herman Plaza. There are hundreds of bikers dressed both formally and informally, and is escorted by the police for courtesy and security.
The environment is quite festive, I remember bikes covered with flowers, bubble making machines mounted on cars, music, bikes that look like a harley davidson, etc. Plus people kindly stop cars and make sure the mass is dense and gap less.
The ride itself is nice and slow, allowing for people of all ages to enjoy it while also paying a visit to SF’s interesting spots. Additionally, the hills and the dusk light makes for great pictures, not to mention visiting the seaside and the Palace of Fine Arts at night.