Small-town Italy: Montelupone

Hilltop jewel in the Marche region.

Night on the piazza in Montelupone.
  • Night on the piazza in Montelupone.

The Marche region of Italy is rarely included among travel itineraries to Italy. It’s also scarcely mentioned in most guidebooks – yet this may simply enhance its appeal among travelers who yearn to forge a different path in their exploration of Italian culture and history.

After staying in Civitanova Marche and traveling to Urbino, I visited another town in the Marche that is truly unique.

Medieval entrance to Montelupone.

Medieval entrance to Montelupone.

Montelupone is a little municipality that seems encased in a time capsule. Well-preserved buildings dating from the 1300s stand proudly on top of a hill, as they have for centuries. The town has been officially designated by a national committee as one of the best small towns in the country.

I went there with some locals to sample the pizza at what was described to me as “the best pizza in the Marche.” Visiting there on a warm July evening was a magical, memorable experience and quintessentially Italian.

The drive to Montelupone from Civitanova was particularly scenic; patches of sunflowers dotted the rolling golden hills. My host invited a guest, Renata, a native Italian who had also lived in Venice Beach, CA. She remarked that she preferred the countryside of the Marche to that in Umbria, as the landscape has a greater variety of colors. Indeed, the late afternoon sun created a striking tapestry of green and gold as it descended beyond the hills.

As we arrived at the mountaintop where the town was located, we could gaze across the valley at a plateau in the distance and see yet another hilltop medieval town. This region is swirling with them!

We walked through the walled gates of Montelupone and soon reached the town square, Piazza dei Priori.

A local artist, Gianni Compagnoni (left), was exhibiting an incredible collection of his drawings of 19 of the hilltop medieval towns in the Marche, called borgos. Even many residents of the area are unaware these borgos have been designated as the finest historically preserved municipalities in the region. Mr. Compagnoni reminisced to me in English about his perplexed reaction at flying into Los Angeles. “I kept looking out the window, wondering where the town is,” he related in a bemused tone.

Gianni has compiled his drawings of the burgos into a book which underscores how historically rich this region is. He gave me a gift of a card with a drawing of a little borgo in the Marche, Montefabbri, with a bustling population of 44. His website is

We then settled ourselves at the pizza restaurant, Pizzeria del Borgo, on the town square, the Piazza dei Priori. Extended families get together quite often here in the Marche, and this evening was no exception. We sat at a long table where friends and families spend hours laughing, joking discussing family matters and (passionately) politics. My host kindly offered me a seat facing the piazza, to better absorb this unique experience.

Pizzeria del Borgo.

Pizzeria del Borgo.

Pizza after pizza appeared in waves, each different, with unfamiliar names like Campagnola and Lardo di Colonnata. There were even some dessert pizzas with chocolate-flavored nutella at the end.

Conversations in Italian swirled around me, some concerning the problems connected with the European Union and high taxation in Italy. Hand gestures were flying and passions inflamed. Renata did her best to translate the finer points to me. I just soaked up the atmosphere.

After dinner we walked through the narrow streets of the small municipality across the shadows of centuries-old buildings. The silence of the night, broken only by soft remarks in Italian and children playing with a soccer ball in the square, added to the special ambience of the town.

“You must visit Ascoli Piceno to the south of here (also in the Marche),” Renata suggested. “It has the second-best square in Italy to Piazza San Marco in Venice.”

I added it to my list of places to visit.

The following evening we went out to dinner in yet another tiny medieval hilltop town in the Marche, Montecosaro. Of course, as always, many extended family members along with their kids joined my host family.

And as with the previous night, we took a walk around the town after dinner for another memorable, atmospheric stroll.

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Great story Derek! I have never even heard of Montelupone. However I did work just north up in RImini for a while. Check out the story-

I have been laying low but I have some great stories brewing.

Thanks, Matt. Looking forward to your stories.

Author's Note: "Monte Cosaro" should be "Montecosaro."

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