Stubborn as a donkey, Via del Borgo or Via degli Asini (The Donkey’s Road) has shuffled along since it was built in the 14th century. One of the most fetching features of medieval Brisighella is this arched passageway that was born as a plain, old road. As with many other roads in the Middle Ages, it was used as an outpost for guards. The road was later covered and converted into housing for the families of men who carted gypsum from the neighboring caves and hills.

Stumbling over the buckled pavement and under its weather-worn wooden beams, it’s not impossible to imagine the way it once was. The carts and stables were at street level, awaiting the next day’s work in large rooms carved from the chalky rock. The stables were nestled against the covered road on the second level, and the families roosted above.

Via Degli Asini is the most charming way to access Brisighella’s three other jewels on opposing hilltops: its well-preserved fortress, the church of Saint Michael and John the Baptist, and the clocktower. Today, the route is home to private residences and businesses. Peering down from the numerous arches onto the street below, visitors can see one of the most pleasant spots for an afternoon spritz: Caffè della Loggia. It offers both a view of the clock tower and an excellent aperitivo.

If somehow the rich history doesn’t draw visitors to Brisighella like hungry donkeys to a pile of hay, its vast array of hiking and biking opportunities might do the trick. The town also hosts seasonal festivals and the occasional concert in one of the numerous caves that dot the area.