Stuart Street is one of the main streets of Dunedin, New Zealand. As with many of Dunedin's streets, it is named after a main street in Edinburgh, Scotland.
Stuart Street runs orthogonally to the city's main business district of George and Princes Streets, meeting them at The Octagon, the city's centre, where it is briefly interrupted by the Octagon itself. This divides Stuart Street into two separate streets, Upper Stuart Street and Lower Stuart Street.
Upper Stuart Street climbs steeply from the Octagon, crossing Moray Place and continuing up to pass through the city's Town Belt and up to the suburb of Roslyn. One of Dunedin's landmarks is the Roslyn Overbridge, which crosses Upper Stuart Street at Roslyn; shortly beyond this point Stuart Street becomes Taieri Road, the original road leading out of Dunedin toward the Taieri Plains in the hinterland to the southwest.
Until the mid 20th century, Upper Stuart Street ran from the Octagon only as far as the junction with York Place. The contract for the north-western extension of Stuart Street, incorporating the former Albert Street (which ran from York Place to London Street) and cutting through the Town Belt to Roslyn, was let in 1949. These works, which were completed in 1954, also required the demolition of Littlebourne House, which had been gifted to the City by the children of the former Mayor, the late Sir John Roberts, in 1934.
Below the Roslyn overbridge, nestled within the town belt, lies Dunedin's main swimming pool, Moana Pool, and the imposing structure of Otago Boys High School. Below this are the former buildings of the Otago Polytechnic (now located in the city's north end), including the King Edward Technical College. Closer to The Octagon, at the junction of Moray Place is the Fortune Theatre. In the block immediately above The Octagon are St. Paul's Anglican Cathedral and a distinctive series of historic terraced houses, now restaurants and boutique shops, which have a Category I Heritage New Zealand classification.