The old town of Kuressaare is compact enough to cover in an hour and worth an hour of your time. Lossi Street runs from the main square toward the castle and is the main promenade of the historic core — wooden houses in faded pastels, low-slung and unpretentious, with carved wooden detailing on the older ones. The neoclassical town hall on the central square dates from 1670 and is still in use; the weighing house beside it now serves as a tourist office.
The central square has a handful of cafes with outdoor seating and hosts occasional markets. The town wears its history lightly: the German name Arensburg, used for centuries, gave way to Kuressaare in 1917, then Kingissepp under the Soviets, then back to Kuressaare after independence. The names changed; the streets did not.