San Cristóbal de las Casas was founded in 1528 by Spanish captain Diego de Mazariegos following a bloody four-year conquest of the region’s dominant indigenous groups, the Zoques and the Chiapas. Mazariegos originally selected a spot along the steamy Río Grijalva in order to keep an eye on the largest Chiapa settlement a few kilometers distant, but within a month rampant disease forced him to relocate to higher ground and the present location.

The new city was originally called Villareal de Chiapa de los Españoles, the first of many names it would sport over the centuries. In 1535, it was renamed San Cristóbal de los Llanos, after the city’s patron saint, then Ciudad Real de Chiapa just a year later. That name stuck for almost three centuries, until 1829, when city leaders adopted the name Ciudad de San Cristóbal, and finally today’s San Cristóbal de las Casas, in honor of the crusading anti-slavery bishop Bartolomé de las Casas.

And so it remained, save a short period in the 1930s and ’40s when it was called Ciudad las Casas (but who’s counting?). Of course, indigenous people had names for this highland valley long before the Spanish did, variations of which are still used today, including Jovel and Hueyzacatlán.

San Cristóbal served as the colonial capital of the Chiapanecan highlands—and the entire region, effectively—through most of the 17th and 18th centuries. But in 1768 Chiapas was divided into two mayoralties, to be governed by San Cristóbal and its lowland rival, San Marcos Tuxtla. San Cristóbal remained the political center, but power was clearly draining to the lowlands, where land that was once ruled by disease-carrying insects was being converted into massive ranches and agricultural estates. The Mexican war of independence further elevated San Marcos, and in 1892 the upstart city—by then known as Tuxtla Gutiérrez—was declared the state capital.

If Chiapas was remote when it was ruled from Guatemala (seat of the Spanish Royal Audience), it was doubly so when incorporated into the new Mexican republic, with its capital in far-off Mexico City. Yet Chiapas is a state rich in natural resources, and for nearly a century the state saw its forests cut and its rivers dammed, while roads, schools, utilities, and other public infrastructure lagged far behind the rest of the nation.

Of course, being ignored suited Chiapas’s vast indigenous population quite well, at least to a point—they went on living as they had for centuries. But eventually native communities saw too much land expropriated and lost too much autonomy; the balance was tipped and discontent boiled over in the form of masked Zapatista rebels storming San Cristóbal’s city hall in 1994.

The Zapatista uprising has since faded in memory and San Cristóbal has settled back into a familiar second-city status, with a rich ethnic and cultural mix and a strong anti-establishment streak. Sure, there’s a Burger King across the street from Revolución Café, but San Cristóbal still manages to feel like an off-the-beaten-path destination, a place that exudes beauty and intelligence in equal measure.