Driving east from the Portuguese capital, the first hilltop castle settlement you’ll hit is also one of the most impressive. Montemor-e-Novo, or simply Montemor for short, has been a settlement from the time of the Romans, and its castle has been renovated and expanded by successive generations of Arab rulers, Christian monks, and Portuguese royals since then. Today the town is a prosperous agricultural hub with a surprisingly happening arts scene, and gastronomic festivals throughout the year. Montemor makes a pleasant half-day stop to or from Évora.

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