There are numerous historic finds, evidence and documents that date the existence of the farm back to Roman times.
The estate is located in a strategic position, between two important communication routes used between the 1st and 2nd centuries A.D.: the Via Lauretana and the Canale Maestro della Chiana (The Master Canal of the Chiana area). The first was one of the main roads built circa 125 B.C. connecting Siena and Cortona, it later joined the Via Cassia; the second was a navigable canal dating from the 3rd century B.C. which, coming from the waters of the Tiber, flowed into the Arno.
Evidence of passage through these communication routes can still be found today in the park in front of the Trerose Villa: the remains of a milestone (which indicated the distance from Rome) and the more recent stone columns by the architect Manetti, veritable street signs dating back to the Grand Duchy of Tuscany (1810). The name of the Estate, as well as its logo, originate from the coat of arms of the family of one of the most influential bishops in the history of the Church, Jacopo Vagnucci (1416-1487), who owned these lands and farms and whose crest included a ''crowned, rampant bear holding three roses in its paw: a red one, a white one and a green one''.
The well, in the gardens of the villa, also included in the winery's logo, dates back to the sixteenth century. It was designed by Antonio da Sangallo the Elder, based on the Dei Grifi e Dei Leoni well in Piazza Grande in Montepulciano and which also inspired the Head of the Lion which outlines the crest of the Trerose trademark.
The heart of the beautiful estate, which stretches over 5 hills, is the prestigious Villa dating from 1521, when Cardinal Silvio Passerini (1469-1529) was nominated Bishop of Cortona and had this building erected in the area between Valiano, Cortona and Lake Trasimeno, bordering the Grand Duchy of Tuscany and the Papal States. Passerini, as well as being a man of the cloth, was the learned patron of Giorgio Vasari, widely mentioned in his book "The Lives", and an intellectual near the Court of the Medicis.
In the underground rooms of the Trerose Villa there are still some signs of his presence: the “Cardinal's Passage”, a secret tunnel leading from the building all the way to Umbria, at the time it was an easy and unnoticed escape route in the difficult years of tension between the Grand Duchy of Tuscany and the Papal States.
The presence of prominent clergymen gives the whole estate a sacred imprint. There are tabernacles, small churches and iconographic evidence scattered all over Trerose, linked to the lives of saints such as Saint Margaret of Cortona, who lived here, or the holy shrine containing the image of Saint Catherine of Alexandria, who the hill is named after.
Saint Catherine is venerated by farmers and livestock breeders because she was martyred for rebelling against animal sacrifices during pagan festivals. She is celebrated on 25th November together with festivals at the end of the grape and olive harvests.
This strong link between religion and agriculture has taken on an undisputed value for Trerose, in fact the vineyard that produces the vintage Vino Nobile is named after the saint.
