Just outside Sheikh, the archaeological site of Fardowsa tells a story that contradicts the town's sleepy reputation. Multi-room stone structures with walls still standing over 1.2 meters high reveal a developed urban settlement from the medieval period, strategically positioned along trade routes connecting the Somali interior to the Gulf of Aden and the Indian Ocean beyond. Excavations have uncovered an Arab coin, glass bangles, and fragments of Chinese porcelain — evidence that this small plateau town once participated in a trading network stretching from the Arabian Peninsula to South Asia and China. Local Somalis have found gold coins at the site on several occasions, likely Persian or Turkish in origin, which they would have exchanged with Arab or Indian merchants at the market in Berbera. The ruins await more thorough excavation, but what has been found already points to a place of considerable economic importance.

By the time the German explorer Josef Menges passed through in the 1880s, the medieval trading center had long declined. But Sheikh was being reborn. Around 1885, Sayyid Adan Ahmad, a Sunni Islamic scholar and jurist of the Habr Awal clan, returned from a decade in the Hejaz and established a religious community — a Tariqa — that became the nucleus of the modern town. When Menges and his party encountered members of Sayyid Adan's community on the plateau, they were met with suspicion and hostility. The Sheikhs suspected the German and his companions were spies seeking to seize their land. Only after Menges's guide, his Abban, engaged in lengthy persuasion did the scholars allow the party to pass, accepting the cover story that they were sport hunters looking for elephants. Menges later offered Sayyid Adan a gift worth six Thalers in gratitude, noting that the holy man lived on the plain with only a dozen Wadaad, or religious scholars.

Perhaps Sheikh's most remarkable feature is the journey to reach it. The Burao-Berbera Highway, one of Somaliland's few tarmacked roads, climbs from the hot, arid coast through the Golis Mountains in a series of dramatic hairpin bends. The landscape transforms as you ascend: the barren coastal lowlands give way to green hills, and the Sheikh Pass crests at about 1,490 meters before dropping to the town's plateau. What appears on a map as a mountain range is actually the jagged northern edge of the Somali plateau — a great escarpment falling away toward the Gulf of Aden. The old airstrip, now disused but still visible from the air, is a reminder that Sheikh once had ambitions as a transport hub. Today, the road is everything, and driving it remains one of the most scenic experiences in the Horn of Africa.

The Pharo Secondary School sits just outside Sheikh, a large campus with a story as turbulent as the country it serves. Founded in 1958 as the SOS Hermann Gmeiner Sheikh Secondary School and run by SOS Children's Villages, it quickly became the most prestigious secondary school in what was then British Somaliland. Its alumni read like a roster of national leadership: former presidents Ahmed Silanyo and Ibrahim Egal both studied here. In 1989, during the civil war, Siad Barre's troops looted and destroyed the complex. It lay in ruins for fourteen years. In 2003, a British couple, Dick and Enid Eyeington, restored the school and reopened it. Months later, they were murdered by terrorists from Al-Itihaad al-Islamiya, who accused the school of converting pupils to Christianity. Despite this tragedy, the school endured. Reopened once more, it maintains strict admission standards, accepting only the strongest students. In 2019, the Pharo Foundation took over management, and the school continues to educate roughly 260 students — a small number carrying outsized expectations.