On an overhang overlooking the Šentrupert Valley, the view opens up over the valley of the river Bistrica with the great Gothic church of St Rupert's on a plateau in the middle of the market town, and the eye turns to the left along the sunny side of vineyard-covered Oplenk with Škrljevo Castle at its foot, setting the seal on the whole of the Šentrupert district with its history and its solid mass, the object of several rebuildings. Further to the left, on a hill, the silhouette of the church on Vesela Gora retreats into the light of the setting sun, while further down, on the north side, the chapel of Our Lady of Sorrows with the little chapels of the Way of the Cross stands on a high hill. Beautiful views open up on all sides: in the west, the slope of Oplenk extends from St Francis Xavier's on Vesela Gora towards the north, with St Barbara's Church on the exposed peak of Okrog; even further north, the gaze rests on the slopes of the Šentrupert hills, dotted with hamlets and covered with forests and vineyards, and on the remote Church of the Holy Spirit above the settlement of Hrastno. Towards the south-east the valley exchanges glances with the highest peak in this area – Debenec – and closes off the view formed by the surrounding panoramas, an enticing glimpse of the life that has gone on here for millennia.
The most valuable monument from the Gothic period is St Rupert's, a three-aisled hall church in Šentrupert. There are very few churches south of the Karavanke mountains, in the territory of central Slovenia, that can be cautiously described as 'original parishes'. In Dolenjska there are only two from the Carolingian period: Šentvid near Stična and Šentrupert. The parish's economic foundations were further consolidated in the 11th century by Emma of Gurk with her deeds of gift. Its strong economic basis attracted the most eminent ecclesiastical dignitaries to Šentrupert. Among those who enjoyed the benefice of the parish were Jacob Auersperger and Jurij Slatkonja. In the period when the remarkable Gothic church was being built, there was quite a succession of distinguished parish priests, including Pavel Glogauer of Blagovica, Hermann Dürrer and, most notably, Ivan Harrer and Jacob Auersperger. Ivan Harrer's connection with Frederick of Cilli brought the most famous architectural workshop in medieval Europe to the Mirna Valley from somewhere in central Europe.