The Church of San Bernardino, now desecrated and abandoned, does not appear in the documents of the pastoral visit of Cardinal Eroli (1465), but it is already described in ruins by Lascaris Bishop (1712). The facade retains a third century portal, with pointed arch and cross license thick relief.

Under the parish church of St. Nicola of Bari, at number 2 of Via del Pago or Pago, whose name remembers the ancient urban aggregate (from the Latin “pagus”), born around the original castle of the ancient Brufa, there is the entrance with portal in stone belonging to the ancient oratory of San Bernardino of Siena, known as Bernardino Albizzeschi (Massa Marittima, September 8^th, 1380 - L'Aquila, May 20^th, 1444), canonized by Pope Nicholas V in 1450. The facade has an entrance consisting of squared and polished stones, stacked together to form the jambs and two low capitals with a light lateral decoration, surmounted by a pointed arch bearing a high keystone at the center, decorated in relief with a thick cross (cross with a sharp lower arm). The portal can be chronologically dated on XIV-XV century. The small church is not present on the official visit made by Cardinal Eroli in 1465, unless one wants to identify it under the title of Santa Croce, former chaplaincy of St. Nicola, documented in the fourteenth century. Originally the building, also known as the Church of San Bernardino and St. Anne, belongs to the Franciscan Order, but by deed dated on March 15^th, 1660, with the help of the notary Francesco Peroni of Monteleone, the friar give the half of the building to the adjoining parish, used as burial ground (cemetery), maintaining the office and the celebration of two masses per year, one during the festivity of the owner and of St. Anne. During the visit made by Mnsr Carlo Giacinto Lascaris, Bishop of Spoleto, on October 4^th, 1712, the Church of San Bernardino, because of its poor conditions, is suspended and the altar painting is transferred to the Church of San Francesco. In the bishop's report, anything but positive, the church is described as "very dark and full of humidity" and more like a "den". The Bishop, informed of the friar property, attested also by a Franciscan coat of arms (no more existing), the "keystone of the door", contacts the Superior Father of the convent to transfer the remain of the stuff. An ancient emblem is also linked to San Bernardino, which is painted on the facade of the building situated in front of the old oratory and probably of the seventeenth and eighteenth century. It consists of the well renown crowned trigram, with the initials "IHS", surmounted by a cross, surrounded by a sun of twelve rays and accompanied by the Holy Nails of the Holy Cross. The trigram "IHS" is associated with the liturgy of the Holy Name of Jesus, but it is especially popular, as in this case, in a cemetery context. With the suppression of the ecclesiastical property in 1866, the Church of San Bernardino is forfeited by the State, together with the other monastic property, and later sold to private and converted at a cellar use. Now the building is a private, deconsecrated and disused property.