Jackson Square buildings built circa 1855.

Moving through any big city can feel like a test of the will. San Francisco is no exception. In the streets surrounding the busy downtown and financial districts, tourists, businessmen, students and homeless people fight for what little space there is. Finding space to get away from the city, in the city is something of an art. After a day spent wandering the sprawling streets of the surrounding neighborhoods, the historical Jackson Square district — the oldest commercial neighborhood in San Francisco — can feel like a much needed breath of fresh air. Now my go-to place when I want coffee, a study break or the feeling of stepping into a bygone era, this tiny chunk of San Francisco real estate attracts little of the hustle and bustle of its neighboring districts but packs ultimate charm.

Unlike other districts in San Francisco, Jackson Square is by no means a destination. The area is filled mostly with offices, too tranquil to allow for the rousing eccentricity that inhabits well traveled neighborhoods like The Mission or Haight Ashbury. But it’s exactly that refined ambiance that makes walking Jackson Square so special.

Strolling down quiet streets filled with stately brick buildings, the atmosphere calls to mind cities of the East Coast or Europe. One is immediately transported in the presence of buildings so old and beautiful. Though relatively It’s hard to believe that this neighborhood had such a colorfully wild past. In the mid 1800s when the Gold Rush hit a fever pitch, San Francisco was transformed from a sleepy town to a booming port city bringing sailors, settlers prospecting for gold and entrepreneurs who sought to make something of themselves. The coastline, which washed up to Battery Street, was filled in, and in the haste to provide more land some 40 abandoned ships from the old port were buried beneath the foundations of the new neighborhood. Merchants, bankers and businessmen quickly populated the area along with sailors who docked there.

However, by the 1870s when the financial district blossomed to the south and fires ravaged the city, the neighborhood emptied, leaving the sailors, prostitutes, pimps, and wholesalers to take the place of the richer class of merchants. Wholesalers brought their production of goods like cigars and whiskey to the area and Jackson Street played host to the city’s red light district. Filled with saloons, factories, dancehalls, and brothels, a citywide newsletter from 1887 noted that it was “the safest place for a criminal to hide.”  It was this lawlessness that gave the neighborhood its original name, The Barbary Coast, taken from the North African coastline of the same name that was home to pirates and traders.

Ohio Street Houses, built circa 1900.

By the 1930s, The Great Depression and Prohibition had changed the atmosphere of the area. Some merchants and seamen remained in the old brick buildings but many buildings stood vacant. The Barbary Coast, mellowed and cleaned up, was slowly absorbed into surrounding neighborhoods until all that remained was a name and a fascinating history. The neighborhood of Jackson Square emerged in its place and in the 1950s began to be preserved and repopulated by San Francisco’s interior designers and antiques dealers. Still home to a thriving commercial and design district, offices, law firms, and interior decor shops maintain the glamor of the oldest commercial district in the city. The best way to see Jackson Square is on foot. Stop off for delicious espresso drinks at the Reveille Coffee truck on Sansome Street as you crisscross your way down Jackson and Pacific Streets.

Or check out Battery Street’s Jackson Place Cafe, a tiny spot tucked inside the courtyard of a brick office building, where you can sit undisturbed while you sip Blue Bottle Coffee and indulge in delicious jelly donuts.

Jackson Place Cafe, 633 Battery Street.

If you’ve worked up an appetite while walking, head over to acclaimed restaurant Cotogna on Pacific Avenue for lunch. The beautiful building that houses the eatery was originally constructed in 1907 and functioned as the Turf Saloon and Concert Hall for many decades.

Cotogna Restaurant, 490 Pacific Avenue.

Round out your walk through Jackson Square by taking in views of the city from the rooftop garden on the 15th floor of 343 Sansome Street, where on nice days, financial district workers have a quiet lunch amidst the surrounding highrises.

For a list of remaining historic buildings in Jackson Square, check out NoeHill’s compilation from the National Register of Historic Places in San Francisco here.