[3] In 1886, the current and second Regatta Hotel, three-storeyed brick building, was erected for Brisbane publican William Winterford.

Each replaced an earlier and much humbler hotel on the site, and in their ornate exteriors, they reflected the optimism and bravado of the booming Queensland economy of the 1880s.

[2] Winterford opened his new hotel in 1887, anticipating a clientele who would be enticed by the river views, the proximity to town and to the Toowong railway station, the weekend regattas on the doorstep, entertainments such as billiards and boating, a well-stocked wine cellar, large well-ventilated bedrooms, family suites, the luxury of hot and cold baths, and good stabling accommodation.

[2][7][8][9] In 2009 as part of the Q150 celebrations, "All chained up for women's rights" was announced as one of the Q150 Icons of Queensland for its role as a "Defining Moment".

[11] The Regatta Hotel, located on a prominent site adjacent to the Toowong Reach of the Brisbane River, is a brick building with hipped corrugated-iron roofs.

[2] The more modest verandahs on the southern and western sides, now somewhat altered, have paired chamfered posts and brackets, and a continuation of the patterned timber frieze.

The bar, formerly a dining room, features a marble fireplace and a pair of curved French doors opening onto the northeast corner of the verandah.

[2] The interiors of the first and second floors retain original finishes including pressed metal ceilings and plastered masonry walls ornamented by arches and mouldings.

The Regatta Hotel retains a substantially intact exterior and a visual prominence along the Toowong Reach of the Brisbane River.

It is important in demonstrating the principal characteristics of a large, ornate 1880s hotel which remains substantially intact.

It exhibits aesthetic characteristics valued by the community, being a prominent landmark contributing to the riverscape along the Toowong Reach of the Brisbane River.

[2] The place has a special association with the life or work of a particular person, group or organisation of importance in Queensland's history.