“Back in the day people from the upper crust of Sydney bought mansions in the Southern Highlands as a wonderful way to escape summer to the cooler climate for a weekend away,” says National Trust New South Wales CEO Brian Scarisbrick.

“It was close enough to head there for just a night or two, and many people still get a lot of enjoyment out of doing it now.” While Bowral is still renowned as a bolthole for Sydney’s elite, what people don’t know is the area is home to a concentration of significant heritage properties featuring everything from mazes, stables, artists’ quarters and manicured gardens fit for a Bronte novel.

“There’s so much wonderful heritage in the area, and now we want to provide the public with the opportunity to enjoy it,” says Scarisbrick.

The National Trust’s Highway 31 Heritage Run is on this weekend. It offers a rare opportunity to tour five grand properties along the Old Hume Highway. There is also a vintage-car rally that will wind through the area. The weekend event also includes a rock’n’roll dance and costume competition, a vintage-car show, a tractor-pulling event and food stalls and food trucks. But for lovers of Downtown Abby the real drawcard is the properties themselves.

They include James Fairfax’s Retford Park estate in Bowral, which was gifted to the National Trust in April this year; Old Government House in Parramatta; Harper’s Mansion in Berrima, Riversdale in Goulburn and Cooma Cottage in Yass. The tour includes morning tea and lunch along the way.

“We want to promote the iconic nature of what we have in the Southern Highlands; the unique heritage and the fact it’s a marvelous day trip from the city,” says Scarisbrick. “There are all these wonderful little shops along the way filled with homemade jams, lovely knick-knacks, and people will love a little retail therapy as they go along.”

The Heritage Run begins in Parramatta at Old Government House, a convict-built Georgian house on a World Heritage site that was the country residence for the first 10 governors of NSW.

Harper’s Mansion in Berrima, a grand vision that was derailed by a 19th-century financial downturn, and which has been lovingly restored by the National Trust, will also open its doors and its maze for the tour.

“You actually do get lost in the maze and they check it at the end of the day to make sure people aren’t still stuck in there before they go home,” says Scarisbrick.

Riversdale in Goulburn is the next stop along the trail, with a tour of a property that once housed inns and schools, before concluding in Yass at Banjo Paterson Park for the Classic Yass vintage-car show. On Saturday night, visitors can stay in Yass for a gala dinner and rock’n’roll-themed dance party. The following morning, breakfast will be served at the Historic Yass Railway Museum, starting a day of free, family-friendly activities around Cooma Cottage, where the Classic Yass Motor Show is presented, including a vintage-tractor pull, antique farm machinery and draft-horse displays, market stalls, music, food and drinks.

“Children will love it, heritage and vintage-car enthusiasts will love it and even the X and Y generations will like it because it offers something unique and different,” says Scarisbrick.

The Highway 31 Heritage Run will take place on November 5–6. Tickets are available here.