With heritage walks, river cruises and tasty delights, historic Windsor is a picturesque escape in the beautiful Hawkesbury and only 50 minutes’ drive northwest of the Sydney Harbour Bridge. In the third-oldest colonial settlement in Australia, begin your discovery on the Windsor Heritage Walk.

On the banks of the Hawkesbury River, Windsor is home to 21 colonial buildings, including one of Australia’s oldest pubs. The 1815-built Macquarie Arms Hotel is the oldest building in Thompson Square, named after wealthy emancipist Andrew Thompson, a policeman, farmer and businessman.

A woman walking by a two-storey heritage building, Windsor

The pretty square is one of Australia’s finest examples of a Georgian town square. Other splendid architecture includes St Matthew’s Anglican Church and the Windsor Court House, both designed by the famous colonial architect Francis Greenway, who arrived in the colony in 1814 as a convict.

Explore the remarkable heritage on a self-guided walk or join a tour with the Hawkesbury Valley Heritage Tours or the Hawkesbury Sightseeing Tours. As well as colonial heritage in the Hawkesbury Regional Museum you'll discover the rich indigenous cultural heritage of the Darug Aboriginal people.

Couple kayaking in afternoon sun, Hawkesbury River

Other things to do include a river cruise on the Hawkesbury Paddlewheeler. In the 1800s steamships were a major mode of transportation to and from the Hawkesbury. Or hire a kayak and explore the tranquil river at your own pace. The riverside Governor Phillip Park is a lovely spot for a picnic.

The vibrant arts scene is a drawcard. The Hawkesbury Regional Gallery has captivating exhibitions and a wonderful collection, including works by famous artists such as Arthur Boyd, Norman Lindsay and Ben Quilty. The fun events calendar includes the Sydney Blues and Roots Festival in October.

Windsor is a great base for exploring other historic towns, the Harvest Farm Gate Trail and the Ebenezer vineyards. Choose too from a tempting range of restaurants or savour lunch on a cruise. Accommodation options range from houseboats to the waterside Crowne Plaza Hawkesbury Valley.