Prior to the founding of Pinelands there was a gravel road that led through the forest to the Maitland Cemetery. Maps of the time aptly named this sandy road, Cemetery Road. With the establishment of Pinelands, this became commonly referred to as Pinelands Drive before being officially named Forest Drive. Forest Drive was intended for fast and heavy vehicles. In 1921 Meadway was built primarily for pedestrians. Stuttaford Avenue was next and was constructed for lighter vehicles and cyclists and then Broadwalk. As the town grew, many more roads were constructed. Where the roads were cut, every attempt was made to follow the contour of the land and preserve pine trees.
Gravel initially used for the roads was mined from Central Square. Roads were originally spray tarred but this proved unsatisfactory and they were later properly tarred. The equipment used was stored at a depot in Central Avenue. The steamroller used to develop the roads in the early days was donated by Garden Cities in 1965, and now resides at Coronation Park.
When Pinelands was first established, a market was planned on a road named Market Way. When the idea of the market was dropped the road was renamed Northway. At the same time, a proposed shopping centre in Broadwalk from Acacia Way to the station was also scrapped and the name of Station Place was changed to Kings Place. South Square at the start of Forest Drive was renamed to Forest Place.
Often residents were consulted in the naming of new roads.
In 1951 the Council asked residents to suggest names for 16 new roads to be built in the new ext. 6. Mrs Simmonds supplied a list with possible names. In May 1952 she made a second list of 16 names and in November another list of 17 names. From the lists Mountain View, Richmond and Ambleside were used. St Andrews Church requested that St Andrews Road be used for the road in front of their church as was done for St Stephens Church. This was declined and the road was named Welgemeend along with the names of Old Cape Homesteads such as Rheezicht, Lancquedoc and Rustenberg being used in the area. It was further decided to name 8 of the roads after South African flowers.
There is only one road in Pinelands officially with an Afrikaans name. When the Council resolved in 1957 to name the roads in extension 8 after South African birds, the Oude Molen Primary School successfully requested the road outside the property be named Lourielaan. There had been a previous unsuccessful request in 1947 by a Mr Conradie on behalf of the 100 Afrikaans speaking residents that the Board consider some Afrikaans Road names in extension 3.
In 1959 three roads in the Howard Centre area were named after personalities who were instrumental in the growth of Pinelands. Lonsdale was named after JP Lonsdale who was first the Estate Manager until 1955. Rose Innes Way was to honour James Rose-Innes, and Stuttaford Way after the founder of Pinelands. However, when the Stuttaford family declined to give permission, this was changed to Gardiner Way after the first Mayor of Pinelands. While the roads were built and named, the Council bowed to public pressure and the Town Hall and library were not built nor was the police Station.
In 1975 the Council decided to give names to all the short unnamed roads in Pinelands which became School Lane, North Link, South Walk, Margaret Place, Chaldon Way and Evening Way.
Sometimes the names given are for obvious reasons. In 1976 Nursery Way was named after the Municipal Nursery at the end of the road which had moved from Riverside. Two years later in 1978 Bowlers Way was named as it led to the Howard Bowling Club.
Scouts Place owes its names to the Saturday afternoon activities by the Scouts while Camp Road is named after the Jubilee Scout Camp held in the area. A curb stone with an inscription was installed to commemorate the event but has since disappeared.
Some name changes came about due to public pressure.
Kameelbult was named due to the camel bones found when constructing the road. These bones were those of the camels that died while being trained at the Police camp at the Oval. In 1936, residents successfully requested a name change to Hillrise.
When Long Place was named in 1938, the Civic Association objected to the name but was ignored. Later in 1944 all the residents in the road signed a petition to rename parts of Long Place, as the unusual shape of the road caused confusion. The Local Board (there was no Municipality yet) agreed. They accepted the names put forward by the residents to rename parts of Long Place to Kingsway, Roseway and Oakdale.
In 1946 the Pinelands Civic Association successfully requested that Links Road, which connected to Links Drive, become part of Peak Drive as Links Drive and Links Road caused confusion. The Association further suggested a list of 14 road names based on South African trees, other Garden Cities and English Lakes. Most of the suggested names were used, such as Ullswater, Coniston, Derwent, Grasmere, Welwyn and Chipstead when new roads were built.