The Upper Tiber Valley occupies the northern corner of Umbria, between Tuscany and the Marche. The wooded hills that stretch between Gubbio and Città di Castello are tied to the hunt for the prized white truffle, whose season in Umbria runs from the last Sunday in September to 31 December. In autumn, three towns along the route hold fairs in its honour. The rest of the year, the itinerary takes in medieval fortresses, parish churches and art towns, following in the footsteps of Federico da Montefeltro and the young Raphael.
Gubbio's grey stone houses climb the slopes of Monte Ingino. The centre of town is Piazza Grande, a hanging square raised on arches and overlooked by the Palazzo dei Consoli. Built between about 1332 and 1349, the palazzo bears the name of its architect, Angelo da Orvieto, above the portal. Since 1909 it has housed the Civic Museum, home to the Iguvine Tables: seven bronze tablets with inscriptions in the Umbrian language, dating from between the third and first centuries BC and engraved partly in the Umbrian alphabet and partly in the Latin one. The town bought them in 1456.
Higher up stands the Palazzo Ducale, rebuilt by Francesco di Giorgio Martini for Federico da Montefeltro, who was born in the territory of Gubbio on 7 June 1422. The duke's inlaid studiolo, made between 1478 and 1482, has been at the Metropolitan Museum in New York since 1939; a copy made in 2009 is on display in the palace.
The Colle Eletto cable car, running since 1960, climbs to 803 metres in about six minutes, carrying visitors in small open baskets up to the area just below the basilica of Sant'Ubaldo. This is where, every 15 May, the three Ceri arrive at a run, the stars of the town's festival. Every 7 December since 1981, the great Christmas tree of lights is switched on across the mountainside: it is about 750 metres high and entered the Guinness Book of Records in 1991.
Between late October and early November, Piazza Quaranta Martiri hosts the White Truffle and Food Products Fair, an event that has been held for more than forty years.
Twenty-three kilometres of winding road north lead to Pietralunga, at 566 metres above sea level, on the ridge that falls towards the Carpinella stream. Around the eighth century the Lombards built a fortress here to control the routes linking Arezzo, Città di Castello and Gubbio. Its pentagonal tower still stands in the main square.
The surrounding area includes about 3,900 hectares of public land, with the Oasi del Candeleto and the Silvio Bambini Ornithological Museum. Over two weekends in October the village hosts the White Truffle and Potato Fair, which reached its thirty-ninth edition in 2026. It is the first of the three truffle fairs along the route, and here the truffle shares the stage with the Pietralunga potato.
Twelve kilometres from the centre stands the Pieve de' Saddi, on the spot where tradition places the martyrdom of St Crescentinus, in 303 under the emperor Diocletian. The church dates roughly from the seventh century and keeps an eighth-century bas-relief showing the saint slaying a dragon. The martyr's relics were moved to Urbino in 1068.
From the hills the route drops to the Tiber plain. Città di Castello is the main town of the Upper Valley and its city of art. The cylindrical bell tower of the cathedral, dating from the eleventh to twelfth century and 43.5 metres high, is one of its most recognisable landmarks.
Palazzo Vitelli alla Cannoniera, built between 1521 and 1532, houses the civic art gallery, the Pinacoteca Comunale. Its most important works include Raphael's Holy Trinity Banner, the Martyrdom of St Sebastian painted by Luca Signorelli in 1498 and a reliquary made by Lorenzo Ghiberti in 1420.
Raphael worked in Città di Castello as a young man. The Baronci Altarpiece, commissioned on 10 December 1500 for the church of Sant'Agostino, is considered his first documented work. The Marriage of the Virgin, signed in 1504 and now in the Pinacoteca di Brera, was painted instead for the church of San Francesco.
Alberto Burri was also born here, in 1915. His works are shown in two venues: Palazzo Albizzini, opened in 1981, and the Ex Seccatoi del Tabacco, opened in 1990 in the buildings once used to dry the tobacco grown in the valley.
One craft tradition still alive is the Tela Umbra, founded in 1908 by Alice Hallgarten and Leopoldo Franchetti, where weaving is still done by hand on looms from the late nineteenth century. Between late October and mid-November the town hosts the National Prized White Truffle Show, spread over three weekends.
Fourteen kilometres further north, Citerna sits on a hill at 480 metres, close to the border with Tuscany. Known as the terrace of the Upper Tiber Valley, it is one of the Borghi più belli d'Italia, the Most Beautiful Villages of Italy.
A covered medieval walkway runs along the walls, with an arched loggia overlooking the valley. The church of San Francesco holds a Madonna and Child in polychrome terracotta attributed to Donatello and dated to around 1415-1420. Rediscovered in the early 2000s, the work underwent a long restoration at the Opificio delle Pietre Dure in Florence before returning to Citerna in 2012.
Sixteen kilometres to the south, at 688 metres, Monte Santa Maria Tiberina looks down over the valley. For centuries it was a small autonomous state, ruled by the Bourbon del Monte family from the eleventh century. Its lords made it a marquisate with its own statutes and its own coinage. It remained autonomous until 1815, when, after the Congress of Vienna, the territory passed to the Grand Duchy of Tuscany.
The village keeps the sixteenth-century palace of the marquises and the Romanesque parish church of Santa Maria. The church has a crypt with the tombs of the Bourbon del Monte and a fourteenth-century wooden Madonna. The castle of Lippiano is also nearby.
The road drops back towards the Tiber and climbs again to Montone, a village listed among the Borghi più belli d'Italia and awarded the Orange Flag of the Touring Club Italiano. The village is linked to the Fortebracci family, to which the condottiero Braccio da Montone belonged: he was born in Perugia in 1368 and died at L'Aquila in 1424 after a battle.
The San Francesco Civic Museum holds Bartolomeo Caporali's Gonfalon of the Madonna of Mercy, dated 1482, a thirteenth-century wooden Deposition and the apse frescoes painted by Antonio Alberti da Ferrara between 1422 and 1424.
The relic of the Holy Thorn, given by the Republic of Venice to Carlo Fortebraccio, Braccio's son, is shown on Easter Monday and during the August festival, when the palio of the three districts is also run. Montone also hosts the Umbria Film Festival, whose honorary president is the director Terry Gilliam.
Nine kilometres further down the valley, on the banks of the Tiber, lies Umbertide. Until 1863 the town was called Fratta: the present name recalls the sons of Uberto, whom tradition credits with rebuilding the settlement, and pays tribute to Prince Umberto of Savoy.
The fortress, built between 1374 and 1389, now houses the Centre for Contemporary Art. The church of Santa Croce, turned into a museum, holds Luca Signorelli's Deposition, painted in 1516 and still in the place it was made for.
Close by stands Santa Maria della Reggia, begun in 1559. The building is octagonal on the outside and circular on the inside. South of the town is the Camaldolese abbey of San Salvatore di Montecorona, which tradition says was founded by St Romuald in the early eleventh century. Its crypt, with five naves, keeps Roman and early medieval columns, no two alike.
From Umbertide it is about thirty kilometres back to Gubbio, where the loop returns to its starting point.
A loop of about 140 kilometres links Gubbio, the birthplace of Federico da Montefeltro, with the valley where the young Raphael painted some of his first documented works. Along the way lie truffle-hunting woods, medieval fortresses, works of art and a village that was once a small autonomous state.
The loop takes three or four days, with time to visit museums, churches and old town centres. In season, white truffle is served in thin shavings over tagliatelle, eggs and crostini. Staying at a farm stay between Gubbio, Umbertide and Città di Castello makes it possible to explore the area at a slow pace and, in autumn, to combine the trip with the truffle fairs.
Those who want to go on into the Marche can continue with the itinerary The Duchy of Urbino, a Renaissance Journey.
