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
former Holy Trinity Methodist Church. 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. ==Lower Stuart Street==