"Tolentino is a relatively nondescript small town which it would be easy to skip in a tour of central Italy. This being Italy, of course, the place is of the hoariest antiquity, a stronghold of the Piceni, a tribe that gave the Romans a good deal of trouble before they were finally conquered, and there are vestiges of both peoples in the town's museum. This being Italy, you will also see several medieval churches, of which the oldest, despite its cold neoclassical façade, is S. Catervo, the cathedral, which dates back to the 4c and preserves the actual 4c marble sarcophagus of St. Catervus: and recent excavations have brought to light some of the saint's original Roman mausoleum. A rather striking 13c towered bridge, tall and narrow, forms the entrance to the city from the S: somewhat predictably monikered the Ponte del Diavolo, or Devil's Bridge.
But such riches are common thruout the Marche — yet Tolentino is not to be skipped, and if you are planning a trip anywhere in the area, you should even make a detour to see it, for the town's one great sight, the Basilica of S. Nicola. St. Nicholas of Tolentino (1246‑1306) was a local man who became a priest in the Augustinian Order, with a talent for gentleness and good sermons: he was canonized in 1446 and his home church, which he knew as S. Agostino, was rededicated to him. It is famous throughout Italy for the Cappellone, a large nearly cubical room adjoining the church proper, frescoed from floor to ceiling in the early 14c."
Lifted from here.
Its west front is a real feast for the eyes - a curly Baroque facade with a grinning sun instead of a rose window and a fancily twisting Gothic portal topped by an oriental-style arch enclosing a dragon-slaying saint.
Inside, the most intriguing feature is the Cappellone di San Nicola , whose Gothic frescoes create a kaleidoscope of colourful scenes of medieval life. In fact, they are episodes from the life of Christ, painted in the fourteenth century by one of Giotto's followers, known only as the "Maestro di Tolentino".
The most striking are The Wedding at Cana , with hefty servants carrying massive jugs of wine on their shoulders, The Slaughter of the Innocents , and The Entry into Jerusalem , in which an attempt at perspective is made by peopling the trees with miniature figures.
In the main piazza is the Museo Internazionale della Caricatura (Tues-Sun 10am-12.30pm & 3-6.30pm; winter closes 5.30pm; L5000/€2.58), which is filled with some of the world's best satirical cartoons. Just east of Tolentino is the imposing, fourteenth-century Castello della Rancia which once harboured the notorious Renaissance mercenary Sir John Hawkwood."
Lifted from this site.