The hill once held a Ngāti Māmoe pā.
 Approximately 300 years ago, it was overtaken by Te Rakiwhakaputa of Ngāi Tahu.
 When the first European settlers arrived, the remains of the pā could still be seen a little to the north of the peak.
 Thomas chose the hill as the base trig station for the survey of the Canterbury settlement.

The first European to farm on the mountain was Joseph Greenwood of Purau, who took up land in 1846 and built a stockman's hut near the peak.
When Greenwood left for Motunau in May 1847, he sold the land to Rhodes brothers (William Barnard and George).
 Major Alfred Hornbrook arrived in Lyttelton in September 1849 and was well established by the time the first wave of settlers (called 'The Pilgrims') arrived on the First Four Ships in December 1850.

Edward Ward, the eldest brother of Crosbie Ward, was one of the Pilgrims.
On his first day in New Zealand, having arrived on the Charlotte Jane, he climbed Mount Pleasant to get a view of the Canterbury Plains.
He stood by the hut built by Charles Crawford, who was managing Mount Pleasant for the Rhodes brothers, when he remarked the following:
All around the soil teemed with vegetable productions – wild oats, ripe sowthistle, plantain, groundsel & other plants grew large and strong.
There was a track of a running stream hard by, but springs everywhere.
I could have wished much to have bought the house and all, just as it stood.
It faced the N.E. and the first point of the land where it meets the River Heathcote.
Being rather too high upon the hill was its only disadvantage.

Ward did buy Quail Island instead, but drowned together with his brother Henry in Lyttelton Harbour in June 1851.

With the profits that Hornbrook made from his hotel and trading post, he bought Mount Pleasant from the Rhodes brothers in March 1852.
Major Hornbrook is described as a rather eccentric person, but his public-spirited character also saw him signalling all ships arriving into Lyttelton Harbour from the top of Mount Pleasant.
 Through a public subscription in 1853, a telescope, flagstaff and a set of flags were paid for.
The walking track from adjacent Mount Cavendish down into Lyttelton township was Major Hornbrook's route for getting provisions to his hut on top of Mount Pleasant, and it is still known as Major Hornbrook's Track.
Hornbrook went bankrupt in 1871 at a time when he owned 47,000 sheep across three stations (his Mount Pleasant run had 6,000 sheep), and the land was sold to Richard May Morten and William White.
Morten and White dissolved their partnership in 1879 and put up the land for auction.
Both of them bid for it, and Morten purchased the 6,000 acres (2,400 ha) at £6 per acre.
The old Hornbrook homestead just below the summit burned down just before World War I, and tearooms and accommodation opened in March 1914 on the site.
 The buildings, no longer accessible to the public, are still present and are located just above the junction where Mount Pleasant Road meets the Summit Road.
On Morten's death, the land (by then 6,500 acres (2,600 ha)) was subdivided.
The largest remaining block had 1,500 acres (610 ha), was owned by J. S. Scott and later on his son Peter Scott, and stretched from Mount Pleasant to the Rapaki Track.

Between late 1942 and early 1943, a heavy anti-aircraft artillery (HAA) battery was established near the summit.
A total of 91 buildings were erected, and the battery was staffed between January 1943 and September 1944.
 It was never used in combat.
Of the 21 HAA batteries that were built in New Zealand, this is the only one outside Wellington that still survives, although for most of the structures, only the foundations still remain.
The hill once held a Ngāti Māmoe pā.  Approximately 300 years ago, it was overtaken by Te Rakiwhakaputa of Ngāi Tahu.  When the first European settlers arrived, the remains of the pā could still be seen a little to the north of the peak.  Thomas chose the hill as the base trig station for the survey of the Canterbury settlement.
The first European to farm on the mountain was Joseph Greenwood of Purau, who took up land in 1846 and built a stockman's hut near the peak. When Greenwood left for Motunau in May 1847, he sold the land to Rhodes brothers (William Barnard and George).  Major Alfred Hornbrook arrived in Lyttelton in September 1849 and was well established by the time the first wave of settlers (called 'The Pilgrims') arrived on the First Four Ships in December 1850.
Edward Ward, the eldest brother of Crosbie Ward, was one of the Pilgrims. On his first day in New Zealand, having arrived on the Charlotte Jane, he climbed Mount Pleasant to get a view of the Canterbury Plains. He stood by the hut built by Charles Crawford, who was managing Mount Pleasant for the Rhodes brothers, when he remarked the following:
All around the soil teemed with vegetable productions – wild oats, ripe sowthistle, plantain, groundsel & other plants grew large and strong. There was a track of a running stream hard by, but springs everywhere. I could have wished much to have bought the house and all, just as it stood. It faced the N.E. and the first point of the land where it meets the River Heathcote. Being rather too high upon the hill was its only disadvantage.
Ward did buy Quail Island instead, but drowned together with his brother Henry in Lyttelton Harbour in June 1851.
With the profits that Hornbrook made from his hotel and trading post, he bought Mount Pleasant from the Rhodes brothers in March 1852. Major Hornbrook is described as a rather eccentric person, but his public-spirited character also saw him signalling all ships arriving into Lyttelton Harbour from the top of Mount Pleasant.  Through a public subscription in 1853, a telescope, flagstaff and a set of flags were paid for. The walking track from adjacent Mount Cavendish down into Lyttelton township was Major Hornbrook's route for getting provisions to his hut on top of Mount Pleasant, and it is still known as Major Hornbrook's Track. Hornbrook went bankrupt in 1871 at a time when he owned 47,000 sheep across three stations (his Mount Pleasant run had 6,000 sheep), and the land was sold to Richard May Morten and William White. Morten and White dissolved their partnership in 1879 and put up the land for auction. Both of them bid for it, and Morten purchased the 6,000 acres (2,400 ha) at £6 per acre. The old Hornbrook homestead just below the summit burned down just before World War I, and tearooms and accommodation opened in March 1914 on the site.  The buildings, no longer accessible to the public, are still present and are located just above the junction where Mount Pleasant Road meets the Summit Road. On Morten's death, the land (by then 6,500 acres (2,600 ha)) was subdivided. The largest remaining block had 1,500 acres (610 ha), was owned by J. S. Scott and later on his son Peter Scott, and stretched from Mount Pleasant to the Rapaki Track.
Between late 1942 and early 1943, a heavy anti-aircraft artillery (HAA) battery was established near the summit. A total of 91 buildings were erected, and the battery was staffed between January 1943 and September 1944.  It was never used in combat. Of the 21 HAA batteries that were built in New Zealand, this is the only one outside Wellington that still survives, although for most of the structures, only the foundations still remain.
Mount Pleasant (New Zealand)