Historically this area was originally settled during the Bronze Age by the Gauls, but subsequently conquered by the Romans who established a defensive fort and colony where Menaggio now sits. The town was linked to by a major Roman highway, the Via Regina, to other parts of the Empire over the Alps and the Southern territories.

Because of Menaggios' strategic location on the Via Regina, during medieval times, Menaggio was surrounded by walls (remnants of which still exist),towers, castles and various other fortifications, which historians visit this region of Lake Como to explore.

Centuries later citizens of Menaggio were actively involved in a process (the Risorgimento) a process that in 1805 culminated in the annexation of the region of Lombardia by the Kingdom of Sardegna.

Menaggio remained an important strategic through WW1 and WW2, and one can still find modern day fortifications dating from both wars in the immediate vicinity. Mussolini, the Fascist dictator who allied Italy with Germany during World War 2 was eventually discredited. He attempted to escape into Switzerland, whose border is just 18 kilometers north of Menaggio, but was caught by partisans and executed.

By the end of the 19th century, Menaggio, like other of the principal towns on Lake Como, had become a well-known tourist retreat, attracting the very wealthy who built marvelous lakeside villas, many of which have now been converted to comfortable, sometimes grand, lakeside hotels.