The Shakespeare Hotel is a notable example of late-Victorian urban corner pub architecture. Located on the Hobson Street ridge, it has close connections with Auckland's Haymarket, where rural produce was brought in to trade from the surrounding countryside.

Some time before the founding of Auckland in 1840, a settlement known as Nga Wharau a Tako was situated towards the northern end of the ridge, one of several nearby locations associated with Maori activity. Following colonial arrival, the site occupied by the Shakespeare Hotel was part of a Crown Grant made to settler David White in 1842. The corner lot changed hands several times before being purchased by Mary Foley in 1897. Foley's purchase occurred in the same year that Buckland's Haymarket constructed new premises on an opposing corner of Albert and Wyndham Streets. Consisting of auction rooms and sales yards, the Haymarket brought in substantial custom from the surrounding countryside and was an important place where town and country met.

Erected in 1898, the Shakespeare Hotel was built following the demolition of earlier timber buildings on the site. Mary Foley's husband Thomas was well-connected, being a nephew to Sir John O'Shanassy (1818-1883), the second Premier of Victoria and a papal knight recognised for his services to Catholic education. The new premises, an imposing brick structure of three and a half storeys, were erected towards the end of a hotel construction boom that followed more stringent requirements introduced under the Liquor Licensing Act 1881. Like most hotels built in central Auckland during this period, the building presented ornately-detailed facades to two streets and was more akin to a retail premises than older public houses.

The building's Italianate design was by Edward Mahoney and Sons, an architectural practice well known for many of Auckland hotels, churches and business houses. The building contractor was J.J. Holland (1893-6), although the interior woodwork was by W. Fairweather who had unsuccessfully tendered for the construction contract. Of impressive visual appearance, the hotel's pale brick facades incorporated bandings of red brick imported from Melbourne. Dormer pediments lighting attic bedrooms formed an unusual feature of the design.

In addition to a corner entrance to the public bar, there was an entrance on Wyndham Street and one on Albert Street, the latter enabling guests to reach their accommodation without contact with bar patrons. Internally, the basement contained a kitchen, cellar, laundry and storerooms. On the ground floor were an office, commercial room, and a single circular bar serving the general assembly-room, front bar and private bar. A dining room and drawing-rooms were located on the second floor. Bedroom accommodation occupied the two upper floors.

The hotel formally opened on 2 July 1898 and was leased to major Auckland brewers Campbell and Ehrenfried who were keen to ensure security of beer supply in a competitive market. Foley retired from the Shakespeare Hotel in 1900, although Mary retained ownership until 1912. Eleven years later the public bar was enlarged and the hallway modified. In 1926 John Hook bought the property which remained in his family's ownership for five decades. The Hooks ran the hotel in conjunction with Dominion Breweries (1930), New Zealand's second largest brewery.

The hotel's traditional mainstay, the Haymarket, relocated in 1927. However, the premises were situated opposite the New Zealand Herald offices and presses on Albert Street, and thrived as one of central Auckland's printers' pubs. Following the repeal of six o'clock closing in 1967, the hotel was granted a tavern licence. The circular public bar was removed to reduce the number of counters and allow more seating. Lavatory facilities were provided for women and a bottle sales outlet was provided. The Shakespeare, ‘which had always had a ‘back bar’ gay clientele’ became the city’s ‘major gay pub’ in this period. Later closing brought more revenue and the pub was renovated, ‘with the two upstairs rooms becoming the gay ones, with the public bar down stairs having a weird selection of clientele’. According to one patron, the upstairs attracted ‘gays, trendies and social butterflies. Tendency to be cliquey; some drag’.

In 1986 the Shakespeare Hotel became New Zealand's first brewpub. The former cellar was converted into a restaurant and the first floor became a lounge bar. Patrons included staff from the new District Court erected on the former Haymarket site. Maintaining a long association with journalists, the hotel became the home of the Auckland Media Club. In 2005 surviving bedrooms were renovated as boutique-style accommodation. The Shakespeare Hotel continues in operation as New Zealand's oldest contemporary brewpub.

The Shakespeare Hotel has aesthetic significance as an ornately-detailed Victorian urban corner pub and is a familiar feature of Auckland's Hobson Street ridge. It has architectural significance for its Italianate design and as a work by the prominent Auckland architectural practice Edward Mahoney and Sons. The building has architectural significance as an increasingly rare example of a late-Victorian corner hotel. It has historical value for its associations with the Haymarket and for reflecting a century of change in liquor licensing and the hospitality industry. As one of the city's well-known printers' pubs, the Shakespeare Hotel has social significance for its strong association with Auckland's news media and as a longstanding place of drinking and social interaction.