Hawkins was born in Invercargill but has lived in Dunedin since 2002 to study at the University of Otago. He lives in Port Chalmers with his wife and son. In 2016, he was involved in a near-fatal car accident after skidding on black ice in Halswell near Christchurch. He had to be cut free from the car and suffered a fracturedhumerus. His wife and son had minor injuries. He does not drive and is known to hitchhike from his home in Port Chalmers. Hawkins is a vegetarian.
Hawkins first stood for Council and Mayor in the 2010 local body election but was unsuccessful after ranking 13th with 3.22% of the vote. In 2013, he was elected to Dunedin City Council in the Central Ward as a representative of the Green Party. His campaign for the mayoralty was unsuccessful coming fourth with 7.5% of the vote. In 2015, he was part of a successful campaign to save, strengthen and restore Dunedin's courthouse building after it was deemed an earthquake risk. In 2016, he was re-elected to Council. He contested the mayoralty for a third time, but was not successful and came fifth with 7.7% of the vote. He stood for re-election to Council and for the mayoralty in 2019 as a representative of the Green Party. He was successful in the mayoral poll and was the first official Green Party candidate to win a mayoralty. As of September 2019, he is the chair of council's community and culture committee, grants committee, refugee steering group and the Mayor's taskforce for housing. He is also a member of the Dunedin Fringe Arts Trust board and the Blue Oyster Arts Trust board and the co-chair of Local GovernmentNew Zealand's young elected members committee. In 2019, he successfully led a motion asking Councillors to support the protection of Foulden Maar. On 12 October 2019, he was elected as Mayor of Dunedin. In May 2020, the Dunedin City Council approved a set of controversial measures designed to entice the public back into the CBD following the COVID-19 lockdown. The main street's speed limit was lowered from 30 km/h to 10 km/h, free parking was introduced and businesses were enabled to use footpaths for free. The measures were criticised by opponents as "ideological". Hawkins respond "This has been called part of a wider ideological drive, well of course it is. Everything is ideological... Every opinion expressed by every person in this room is a product of ideology. A product of your values, your knowledge and your perspectives and your opinions. That's what that means.".
