The first winter weekends was held in 2007. Prior to this, Port Fairy's main winter time activity was Rhapsody in June, an event built around musical and artistic pursuits.

The very first winter weekends in 2007 featured an early version of the now world-renowned Dachshund Dash.

The running of the event took place on the then Village Green, with 30 entries received. Owners brought their dogs from as far afield as Mount Gambier and Mornington, with heats followed by the final, which was called the "Mass Dash".

The weekend featured a number of competitions. Warrnambool's Melissa Bowman won the songwriting competition, while Leah Ramsay was the winner of the bread and butter pudding bake-off.

When it came to entertainment, comedy was at the top of the bill. New Zealand comedian Alan Brough, who at the time was enjoying a wave of popularity due to his starring role in the ABC hit TV show Spicks and Specks, was the star attraction.

Music for the weekend was a varied menu and included a Women in Song concert, which featured artists such as Oriel Glennen and Marcia Howard.

The weekend was also a forum for some talented up and coming performers.

Young roots performer Tom Richardson headlined a FReeZA event and art also played a part with school children helping to create a mural.

Winter Weekends coordinator Monica Sammon said the inaugural event was a big success.

"We now have a better idea of what is going to work and what is not going to work," she said at the time.

"The target market is people aged 40 and above who are happy to pay for quality events. We will keep all events tight and get smarter."

She praised businesses and residents for their support of the event and added that people got behind the theme of the festival, which was the colour red. Red flags decorated the town's CBD while red scarves were a popular fashion item.

"The atmosphere around the town was fantastic," she said.