Heritage towns in Comunidad de Madrid (Madrid Region)

Chinchón's Plaza Mayor — a ring of timber balconies and arcaded facades that has hosted bullfights, executions, and Orson Welles — makes this Madrid province town one of the most distinctive squares in Spain.

A medieval walled town in the Sierra de Madrid where a Gothic-Mudéjar castle, a nearly complete circuit of Muslim-origin walls, and a river-spanning defensive gallery survive in remarkable condition above the Lozoya valley.

A town whose limestone quarries built half of Madrid, whose plaza mayor hosted medieval royal courts, and whose castle ford was crossed by Hannibal himself — Colmenar de Oreja carries an outsized history for a quiet Castilian town on the Tajo.

Founded in 1499 by the city of Segovia to hold disputed borderland, Navalcarnero grew from five farmers into a Madrid-province town that was burned four times and fought over in the courts for over a century.

A planned royal industrial town east of Madrid, its circular plaza, factory façade, and castle-palace preserving the full ambition of 18th-century Bourbon reform in stone and brick.

A former seat of the Military Order of Santiago in the Madrid region, its keep, monastery, and parish church standing together as a declared Historic Site with roots stretching back to the 11th century.

A royal seat on the confluence of the Tagus and Jarama rivers, Aranjuez holds a Renaissance palace built by the architects of El Escorial, vast formal gardens, and a human history stretching back to the Palaeolithic.