"Bowral - if you can afford it" a Bowral Travel Page by iandsmith

I should add that the above tag is mine. Since the town has more than twice the population of any other in the region I think it deserves the title.
One of the things that gets your attention fairly early on is that this is a place where money isn't a problem for some of the locals or, for that matter, many of the visitors.
There's lots of quality shopping and dining here so, as they used to say in a famous old ad, "Don't forget, bring your money with you".
One thing that really surprised me not only about Bowral, but about the whole Southern Highlands, was the lack of art galleries. I thought there would be heaps but they are fairly thin on the ground. Having said that, they try to make up for that shortage with antique shops.
Bowral is situated in a valley at the foot of Mt. Gibraltar, largely on land originally granted to John Oxley, famous explorer of the early colony of NSW. For a generation it was farmed by his sons.
With the coming of the railway in the 1860s, the Oxleys subdivided part of the land for a private village. On this land (not much bigger than the current shopping centre, part of which is named after them) a town grew.
Soon, there was a railway station, churches, schools and public buildings. There were also many guesthouses and private 'holiday houses' that sprung up, its proximity to Sydney making these a viable proposition.
As early as 1886 Bowral was gazetted as a Municipality, and the corporate life of the town began. Within 20 years it had over 1000 citizens and many community, social, and sporting organisations.
Land around the town was progressively subdivided and added to the Municipality, but most of the surrounding farmland and countryside was controlled by larger shires, and Bowral remained a purely civic centre.
It became the "big town" of the Highlands, with its well paved streets, neat residences, many businesses, and municipal amenities (such as a gasworks and electricity). Its main industries were tourism, a large brickworks, a milk processing factory and services for surrounding farms.
In 1981 the Municipality was integrated into the new Wingecarribee Shire.
Today Bowral has over 14,000 inhabitants, with new residential subdivisions expanding east of the town. Many of its recent residents are 'refugees' from the city looking for a better lifestyle, commuting back to the city on the freeway to their jobs.
The beauty of townscape and countryside, and the climate - enhanced by over 100 years of plantings of exotic deciduous trees, "English" gardens, and annual massed displays of bulbs and perennials - gives it a unique attraction in the Australian countryside - especially in the leafy area of Burradoo with its fine houses and gardens stretching south towards Moss Vale.
Its well kept appearance and manicured gardens make this a very pleasant place to visit.
Thanks to VT member "ragsie" for this next bit: If anybody remembers the Ginger Meggs movie filmed in Bowral, the building in the above photo was the location used as Polly's house (where Ginger sneaks into Polly's birthday party dressed as a girl, and causes a food fight).

This is a rustic little cemetery on one of the side roads in the area. There are many scenes like this to be had in the Southern Highlands.