Coins found near Pontresina indicate that the area was already populated during the Bronze Age. The first reference to Pontresina is found in the Gamertingen charter for the years 1137 – 1139. The name Pontresina is derived from "Ponte sarasinae" and means a bridge constructed by the architect "Saraschin". There was already considerable traffic over the Bernina Pass in the Middle Ages. Continuous summer rail operation has been in place since 1910. This period saw rapid growth for Pontresina as a tourist and health resort.
| 1138 | Formation of the current parish, own statutes drawn up in 1587 |
| 1549 | Introduction of the Reformation by Pietro Paolo Vergerio, former Bishop of Capo d’Istria |
| 1720 | A blaze destroys almost the entire part of the village known as Laret and part of the parish archives stored in the attic of San Nicolo Church |
| 1842-1864 | Construction of the Bernina road / opening in 1864 |
| 1849 | Swiss Federal Post travels over the Bernina Pass with its big yellow sleigh for the first time |
| 1850 | First summer guests in Pontresina |
| 1905 | First year of winter operation |
| 1907 | Commissioning of Muottas Muragl Railway |
| 1908 | Opening of the Samedan-Pontresina Rhaetian Railway line |
| 1910 | Continuous summer service on the Bernina section of the Rhaetian Railway to Tirano (5 July 1910) |
| 1937 | Construction of the Chantatsch ski lift |
| 1945 | The chairlift to Alp Languard is completed |
| 1956 | Construction of the Diavolezza cable car lift |
| 1963 | Opening of the Piz Lagalb cable car lift |
| 1969-1970 | Construction of the public swimming pool / opening in 1970 |
| 1980 | Opening of the new Diavolezza cable car lift (125 persons per cable car) |
| 1990-1992 | Construction of the Mulin multi-storey car park / opening in 1992 |
| 1991 | Rebuilding of Alp Languard chairlift |
| 1995-1997 | Construction of the Convention and Event Centre Rondo with multi-storey car park / opening of multi-storey car park in 1996 / opening of Convention Centre in December 1997 |
| 2001-2003 | Construction of Pontresina levee at the foot of the Schafberg / inauguration in 2003 |
| 2002 | Completion of the redesigned Via Maistra and opening of shopping mile |
| 2003 | World Ski Championships in St. Moritz-Pontresina/Engadin |
| 2004 | Swiss cross-country ski championships |
| 2004 | 100th anniversary of the Bernina Ski Club |
| 2004 | Acquisition of the Chamanna Segantini by the parish of Pontresina |
| 2006 | Adoption of new tourism legislation in the Engadin |
| 2007 | Integration of Pontresina tourist services into the new tourism organisation Engadin St. Moritz / termination of operation of the Pontresina health resort and tourism service |
| 2007 | Opening of the Bellavita Pool and Spa |
| 2009 | Construction of La Resgia via ferrata |
| 2009 | Redesign of Cuntschett sports field with two beach volleyball fields |
| 2010 | 100th anniversary of the resort orchestra and today’s Camerata Pontresina |
| 2010 | 100th anniversary of the Bernina Railway Line |