The part of the street immediately below The Octagon is the steepest section, as the road traverses an old cutting through Bell Hill.

The stone removed from the hill was used as construction material for many of the city's first permanent buildings, and also as fill to reclaim the northern end of the Southern Endowment along the edge of the harbour.

The area of Princes Street between the Exchange and Market Reserve was a frequent source of dispute in the early years of European settlement.

Captain Cargill, the founder of the new city, wished to follow the British practice of keeping the foreshore as public land.

As the town spread, the area around the landing site became populated by settlers, and visiting Māori relied on the coastal strip as a place to set up their encampments.

Mantell and Cargill, who had been bitter political opponents for the control of the early settlement, quickly found themselves at loggerheads over the proposal, and disputes over the ownership and allocation of the land dragged on for over two decades, finally being settled in the courts in 1877.

[7][8] In the years following the Otago gold rush of the 1860s Dunedin grew rapidly, with much of the growth being centred on Princes Street.

Many of the prominent grand buildings of this part of Dunedin date from this period, and numerous structures in the area have New Zealand Historic Places Trust classification as a result.

[15] Massive reclamation of the area led to the creation of a wide strip of land, since occupied by commercial premises, warehousing, and the main rail line.

[16] A spring which fed the stream is still used as the source of water for Speight's Brewery, which is located 200 metres to the northwest on Rattray Street.

This monument, designed by Charles Robert Swyer and built in 1863-4, was originally sited in the Octagon, but was moved to the Exchange in 1872.

[19] Other sculptures in John Wickliffe Plaza include "We are not alone", a group of three stylised penguins created in 1999 by Parry Jones.

Wain's Hotel, immediately opposite the former Post Office building, is an imposing Italianate structure built in 1878 from designs by Mason and Wales.

[22] Lower Princes Street rises slightly from the Exchange before dropping down, becoming flat for the final kilometre of its length.

The street itself widens from thee crest below the Exchange, becoming a dual carriageway from this point south to the major junction at the southern end of the Oval.

[24] The Market Reserve also contains a children's playground and, at the edge closes to the Crown Roller Mills Building, a small monument dedicated to Otago workers who have lost their lives while at work.

[25] At the bottom end of Princes Street is the former Dunedin Metropolitan Club building, now home to Natural History New Zealand, one of the country's leading television production companies.

Kensington Oval contains mainly cricket and association football pitches, and also caters for rugby, hockey, and softball.

The Southern Cemetery's earliest graves are from 1858, and it contains the remains of many of the city's founding fathers, including Captain William Cargill, Thomas Burns, and Johnny Jones.

[29][30] The top section of Princes Street, from the Octagon to the Exchange, has for many years been a nexus for Dunedin's public transport system.