Upper Old Town is known locally as Toompea derived from the German word Domberg or “Cathedral Hill”. Given Estonia’s relatively flat landscape, this limestone, table-top, hill served as a natural site from which to rule. For centuries, up to the present day, this has been the seat of various governments. Toompea measures approximately 1,300 by 800 feet (400 x 250m) encompassing about 17 acres (7ha). It’s elevation ranges from 65 to 100 feet (20 to 30m) above the surrounding area.

Toompea has several observation decks offering wonderful views of lower Old Town, the harbor and beyond. It’s primary feature is a castle dating to the 13th century (Toompea Hill was used as a stronghold as far back as the 9th century). Toompea Castle is guarded by a tower known as Tall Hermann measuring 157 feet (48m). Other notable buildings include St. Mary’s Cathedral (Lutheran) from the 13th century. This is the oldest church in Tallinn. Stenbock House and Alexander Nevsky Cathedral (Russian Orthodox) are both relatively new dating only to the late 1800s.

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