Hoodline has a fascinating article describing how Divisadero Street ended up getting connected to Castro Street.
They weren’t always connected. Initially Divisadero just sort of stopped. But both the Western Addition and the Castro, largely spared from the ravages of the 1906 earthquake, prospered in the early twentieth century. By the 1920s, automobiles were becoming much more abundant, and decades before the Federal highway program there was talk about building a freeway that would stretch from Alemeny Boulevard on the south side of the City to Lombard Street on the north.
The idea became even more important when talks got more serious about building a controversial bridge to span the Golden Gate.
From Hoodline:
Working closely with the Castro Improvement Club (another neighborhood group), the EVPA [Eureka Valley Promotion Association] raised money and rallied political support – with the priority being the Castro-Divisadero street connection.
By 1934 the city had purchased $50,000 worth of lots in the Castro and Divisadero area with the intention of buying up $55,000 more to clear for a new cross-city highway. Another $70,000 was budgeted for construction purposes, such as widening the road to 60′. Plans were put into place to reroute cable cars to side roads, and a tunnel was planned in the northern Marina-end of Divisadero to expedite traffic to the bridge. (Calculated for inflation, this adds up to around $3 million in 2014 dollars.)
– Hoodline, September 21, 2014
Hoodline has a whole lot more about how connecting the streets ties in to dreams of a network of freeways throughout the City … and the resulting neighborhood groups that cropped up to protect the City and their neighborhood.