In 1791, the Wide Street Commission laid out a plan for the development of the area and a major roadway was established called Great Brunswick street in honour of King George I of Great Britain, the Duke of Brunswick. Soon after, buildings were constructed opposite the walls of Trinity College Dublin , where the hotel now stands.
The first buildings on the site were constructed in the early 1800's. The buildings at 23,24,25 and 26 Pearse Street were built in 1818. The facades were refurbished to their former glory along with the interior of the buildings, with the extension ready to greet guests who flocked to Dublin because of the 2006 Ryder Cup.
Among the best known of Dublin businesses occupying this site was Robert Tedcastle's Coal Merchants, which began trading at 19-20 Great Brunswick Street in the 1850's and remained until 20th century. Evidencing his success, Tedcastle purchased the historic Marlay House in Marlay Park, Rathfarnham and his enterprise continues today in the form of TOP Shops, an abbreviation for Tedcastle Oil Products. From 1910 until 1924 the British Army Recruiting Office stood at 23-25 Great Brunswick Street. Between 1914 and 1918 alone over 250,000 Irishmen volunteered to serve in the British Army and many of them passed through what is now a modern hotel. Over 35,000 of these men were killed in World War One.
Ironically, Padraig Pearse, the executed leader of the 1916 rising and author of the Easter Proclamation declaring Irish Independence was born at a couple doors down at 27 Great Brunswick Street in 1879. Padraig's father James, an Englishman, established an Ecclesiastical Architecture and Sculpture firm fashioning stone and marble altars and gravestones at the site a few years before Padraig's birth. The original house stands as an historic memorial while the Trinity Capital Hotel occupies the back garden where the Pearses once worked and played. In February 1923 the name of the street was changed to Pearse Street to honour Padraig and his brother Willie who was also executed in Dublin after the 1916 Uprising.
Between 1906 and 1909 the Dublin Fire Brigade established its headquarters at number 14 where Pearse Street intersects with Tara Street. The station served the people of Dublin for nearly 100 years until a new station was established on Townsend Street although emergency equipment still exits onto Pearse Street under the hotel. The Trinity Capital Hotel has preserved the original exterior of the station including the watchtower, which has been developed to incorporate it into the Hotel.