Various objects found near Pontresina indicate that the area was populated during the Bronze Age. Only recently, excavations in the Val Languard resulted in finds which point to an 8000-year history of settlement. A coin found dating back to Roman times bears the image of Emperor Trajan. The first reference to Pontresina is found in the Gamertingen charter dated 22 January, 1139. The children of Gamertingen donated everything they owned in ‘pontem Sarasinam’ to the Bishop of Chur – for the sake of their parents’ salvation.
According to a document in the Episcopal archives in Chur, in 1244, Tobias de Pont Zarazino was responsible for losing the Episcopal valley chancellery previously held by his family. The rulers of Sarrazeno or Zarazino held office thenceforth as ‘deputati juridici’. The parish of Upper Engadin helped to establish the communal place of worship in Zernez in 1367. Around the middle of the 14th century, the Upper Engadin valley parish was divided into two communities. Disengagement from the Bishopric of Chur was achieved peacefully by the communities buying themselves out and was completed in 1526. Territorial disbanding into the current Upper Valley communities took place in 1538. The parish subsequently established its own statutes, which were recorded for the first time in 1587.
Historical documents indicate that a settlement must have existed in the extensive meadow area between Foppas and Charers. A similar settlement that was inhabited all year round must have been located near the Bernina Pass. In ecclesiastical terms, Pontresina belonged to Pleif San Peter in Samedan. As early as 1520, it employed its own chaplain and became an independent parish after 1527. Pontresina was the first Upper Engadin parish to adopt the reformed faith in 1549.
The Burial Church of Sta. Maria is known to be the oldest village church. It is thought to have originated in the 11th century and was renovated and extended in 1460. The Chapel of San Spiert was built by the priest Johannes Maurizius Tempesta, who constructed it using his own funds in 1485. An additional chapel was constructed on Bernina-Suot in 1519. In 1876, an Anglican church was built in the new part of the village known as Bellavita. The construction of the Catholic church took place in 1923.
Historically, schooling took place in the teacher's house or a private home. However, a new schoolhouse was built as part of the village’s communal facilities in Bellavita in 1871. From then on, two teachers were employed. In 1933, an additional floor and an annexe were added to the schoolhouse. Until 1933, tuition was in the Romansh language. At the request of a number of parents, the first five primary classes were taught in parallel German and Romansh departments. In 1949, on the basis of the results of this experiment, the school decided to amalgamate the two departments and to re-introduce primary tuition in the Romansh language.
Mining for silver in the neighbouring Val Minor dates back to the 12th century. The well-defined, sunny terraces on the left side of the valley indicate that cultivation of crops was an important occupation in earlier centuries, as well as cattle breeding, hunting and fishing. As early as the middle of the 12th century, many artisans from Pontresina earned their living in other countries. The current ownership of the Bergell parish of Bondo on Bernina is very curious.
On 18 December, 1429, a certain Alycthus de Olgzathe, a resident of Puschlav, sold to the parish of Bondo "full ownership of an Alpine pasture in a place known as Beranya in Val Minore". A few years later, Bondo purchased a second Alpine pasture in Val Minor from an individual known as "Crapp". In 1455, another family by the name of ‘Crappun’ from Celerina ceded its Alpine territory on Bernina to the parish of Bondo. As the result of these three purchases and subsequent consolidation, the parish of Bondo managed to retain two Alpine properties within its sovereign territory.
There was already considerable traffic over the Bernina Pass in the Middle Ages. Construction of the Bernina Pass road between 1842 and 1864 increased trade and traffic noticeably. In January 1849, the Swiss Federal Post travelled up this route with its big yellow sleigh for the first time to the Ospizio Bernina.