Ethiopians in the Middle Ages did not call this province Wollo; they called it Bete Amhara, the House of Amhara, and they considered it the center of their world. In 1270, Yekuno Amlak, a regional lord from Ambassel, overthrew the Zagwe dynasty and established the Solomonic line that would rule Ethiopia, with interruptions, for the next seven centuries. The Zagwe before him had claimed descent from Moses; the Solomonids claimed descent from King Solomon through the Queen of Sheba. Both claims required biblical genealogies that were more theological than historical, but both rested on Wollo, where Lake Hayq's shores held the kingdom's sacred geography. The Monastic school of Lake Hayq, founded in 1248 by Iyasus Mo'a, trained generations of saints and scholars, including Tekle-Haymanot, who lived from 1215 to 1313 and founded his own monastic community at Debre Asbo in Shewa.

Around 1170, at Roha in northern Wollo, King Lalibela commissioned workers to carve eleven monolithic churches directly into the volcanic rock. The churches were not built; they were excavated, quarried downward from the ground surface until their roofs were below ground level, then hollowed out until each became a complete structure with pillars, arches, and bas-reliefs. Bete Giyorgis, the Church of Saint George, was carved in the shape of a cross, its roof still level with the surrounding plateau so that you walk up to the edge and look down into the church. The town was renamed Lalibela after the king whose vision had created it. The legend says angels helped with the night shift. The churches are a UNESCO World Heritage Site, still in daily use by the Ethiopian Orthodox Tewahedo Church, and pilgrims still come on their feast days dressed in white gabbi cloth.

Although Muslims had lived in Wollo since at least the eighth century, the province was overwhelmingly Christian until the sixteenth. Between 1529 and 1543, the Adal Sultanate launched an invasion under Imam Ahmad ibn Ibrahim al-Ghazi, known in Ethiopia as Ahmad Gran, whose armies burned monasteries, destroyed churches, and seized relics across the highlands. Some of the great Wollo churches, including the magnificent Mekane Silasse Church that Atse Naod began in 1489 and his son Lebna Dengel completed in 1513, were destroyed in the war. The Portuguese priest Francisco Alvares had attended Mekane Silasse's inauguration and described walls of carved stone, doors plated in gold and silver, and sixteen curtains of golden cotton. None of it survived. Oromo expansion into Wollo in the late sixteenth century brought a second wave of religious change: Oromo clans who settled in the province gradually adopted Islam, and what had been the heart of Ethiopian Christianity became, in places, the heart of Ethiopian Islam.

Wollo in the twentieth century endured two catastrophic famines. The first, in 1973, followed several years of drought and was concealed from the wider Ethiopian public and the international community by Haile Selassie's government. Jonathan Dimbleby's BBC documentary 'The Unknown Famine' showed the world what was happening: villages where children had stopped crying because they had no strength left, families walking for weeks toward food aid they might not reach in time. The famine contributed to Haile Selassie's overthrow by the Derg in September 1974. The second famine, in 1984-85, was even deadlier, killing an estimated 400,000 people in Wollo and other provinces and displacing millions more. Michael Buerk's BBC reports sparked Band Aid and Live Aid. Famine scholar Alex de Waal has observed that in both cases, the drought was not the cause so much as the trigger: political choices, forced resettlement policies, and counter-insurgency warfare against northern rebels turned food shortage into mass death.

Wollo today survives as two zones of the Amhara Region: North Wollo, with its capital at Weldiya, and South Wollo, centered on Dessie. Parts of the old Wollo that were predominantly Afar were transferred to the Afar Region after the 1995 constitution introduced ethnic federalism. The rock churches of Lalibela still anchor the tourist economy, the monasteries still chant at dawn, and the highland farms still depend on rains that sometimes fail. Wollo is also credited as the origin of the four melodic modes, or kignits, that structure Ethiopian music: tezita, bati, ambassel, and anchihoy. The names of the last two are names of places in Wollo. The music, like the churches, has outlasted the emperors and the famines both.