[3] Wadestown's streets are picturesque and narrow — 10 metres (33 feet), half a chain, made by pick and shovel and horse and scoop.

In 1841, together with another early settler, James Watt, he acquired land in the area now known as Wadestown and divided it into one and two-acre lots.

The eastern parts of the suburb, including Highland Park, are within the enrolment zone of Thorndon School.

[11] The Weld Street campus (previously known as the Side School) is designed for new entrants, and consists of parallel junior classes (Years 1–2).

Although the Rose Street site is hilly, the grounds include a large flat playground, a playing field, landscaped gardens and tennis courts.

[11][10] The majority of Wadestown pupils come from the local suburb but a number also come from Wilton, Chartwell, Thorndon, Khandallah and Crofton Downs.

The original Side School building was demolished after the Second World War and rebuilt in the current design.

The steep hillsides in Wadestown occasionally cause difficulties for the commuter train service deep in the valley.

Highland Park had been bought by Rhodes before 1849 and was part of the original James Watt and John Wade holding.

[29] The Lennel Road cutting with Watt Street bridge was made for the tramway at the beginning of the 20th century and after much illicit use by animals, pedestrians and some vehicles expanded to roadway when the tram service finished in 1949.

It was built in 1885 in response to concerns that Russia was planning to expand its empire in the South Pacific, and was the first fort capable of defending Wellington's port from a naval attack.

It is of national historical importance because the battery is one of the least altered examples of the first defences constructed in the late nineteenth-century in preparation for an expected Russian naval invasion.

Fort Buckley is part of a wider network of coastal defences erected around that time, and its construction reflects New Zealand's increasing independence from Britain on military matters during that period.

It is now a recreation reserve managed by the Highland Park Progressive Association (HPPA) in partnership with the Wellington City Council (WCC).

Special aspects of the area are the central court, the bush reserve around the group of houses, and the very steep, pedestrian-only access.

[36] During the Great Depression and War years, the earliest tenants made full use of the tennis court as a central activity area.

In the 1950s, the Court briefly became a miniature ‘Polish village’, as at one point 13 of the 16 houses were occupied by Poles, many of whom had arrived in New Zealand in 1944 as child refugees.

A documentary film ‘A Place to Stay’, was made by Marie Russell in 2009 about the unique design and unusual social history of Salisbury Garden Court.

Each separate bungalow contained "a large sitting room, 2 bedrooms, kitchenette, bathroom etc, electric light, gas cooker, caliphont, blinds provided" .

"[38] The pressures of the inner-city housing refurbishment boom of the 1970s eventually brought legitimate subdivision of their one site and the ability to deal in and finance individual buildings.

Another historic place in Wadestown (although now strictly located just inside the Thorndon boundary), is the house at 4 Goldies Brae built for original settler Dr Alexander Johnston and designed by him.

Reports on the sale of the property in 2020 claimed that the unique design is based on Gatcombe Park, a British stately home that is the country residence of Princess Anne.

[39] It is unusual because of the continuous glazed gallery (or conservatory) that provides enclosed access to each of the ten rooms.

[41] Goldie's Brae estate with 5 acres of grounds included the area now crossed by Grosvenor Terrace — and some of Orchard Street — all beyond Queen's Park at the north end of Grant Road.

Its land north of the street of the same name was subdivided at the same time as adjoining Highland Park and its subdivision suffered the same decade of Onslow Borough Council obstructions.

The difficulties of building for early-established Wadestown houses adequate drainage within Onslow's boundaries, the subdivision of the Highland Park estate and the appeal to the residents of this very steep area of joining Wellington's tramway system led to amalgamation in April 1907.