Ladd's Addition

William S. Ladd was a banker and two-term Portland mayor who owned a 126-acre farm in what was then East Portland. When the city merged with East Portland in 1891, he subdivided his land for residential development — but instead of following the standard orthogonal grid, he designed a diagonal "wagon wheel" street pattern with a central park and four diamond-shaped rose gardens at the cardinal points.

His surveyor reportedly thought it was a terrible idea. Ladd did it anyway. The diagonal streets create blocks that are technically irregular — your GPS will sometimes struggle with intersections that don't quite align — but the effect is a neighborhood that feels different from the moment you enter it. You're not on a grid anymore.

The rose gardens were formally planted in 1909 under park superintendent Emanuel Mische, with over 3,000 roses of sixty varieties in a stained-glass arrangement. The neighborhood was placed on the National Register of Historic Places in 1988.

Paadee, a Thai restaurant on SE Clinton at the edge of Ladd's Addition, has one of the best cocktail programs in SE Portland to match its consistently excellent food. Stumptown Coffee has a location on SE Belmont nearby. The neighborhood itself is predominantly residential — the surrounding streets (Clinton, Division, Hawthorne, Belmont) provide the commercial options.

Walk the full circuit of the rose gardens in May or June when they're in peak bloom. The central circle — Ladd Circle Park — has a large central garden surrounded by residential streets and is one of the quieter parks in SE Portland. The diagonal streets mean that every walk in Ladd's Addition eventually surprises you with an intersection you didn't expect.