Half Moon Bay is where the Peninsula's mountains finally meet the Pacific. The town sits on a wide coastal plain, backed by the green flank of the Santa Cruz Mountains and fronted by a long crescent of sand, and it feels like a different state from the busy bay side only twenty minutes away over Highway 92. Fog arrives most summer afternoons, so mornings are your best bet for sun.
Riders come through on Highway 1 and use the town as a pause on the coast run. The road here is wide and easy, with long views over fields of artichokes, Brussels sprouts and pumpkins, and it grows tighter and more dramatic south toward Pescadero and Santa Cruz. Highway 92 over the mountains is the classic way in from the east, a tight, tree-lined climb with a few steep switchbacks, and it is worth a ride in either direction. Watch for cyclists, who flock to these roads at weekends, and for the cold, wet patches under the redwoods that never quite dry out.
Half Moon Bay is also a place with some history. It began as a Spanish-era farming spot, and later became known as Spanishtown, and during Prohibition its isolated beaches were used by rum-runners who landed their cargo at night. Today, its biggest annual event is the Art and Pumpkin Festival in October, when the whole coast road clogs with visitors. A few kilometres north, at Pillar Point, huge winter swells break far offshore at a place surfers call Mavericks, and in big storms they are a spectacle even from the cliff.
For practical things, the town has more than twelve thousand people, which means fuel, groceries, bike shops and cafes on the main street are all easy. A bowl of clam chowder and a view of the harbour at Pillar Point is a classic and reliable lunch. Weekend traffic on the coast road can be slow, with long tailbacks heading back over Highway 92 on Sunday afternoons, so plan around it.