Cycling across southern Portugal in search of history — and a workout

So, on a clear October day, I’m muscling my bike up the teeth-rattling cobblestones of Castelo de Vide, a whitewashed village topped with a 14th-century castle. It’s Day 2 on a six-day historical cycling trip through the Alentejo, a fertile southern region of Portugal studded with well-fortified settlements, some dating from as long ago as the 1st century B.C. I’m a history fan and exercise fanatic, so the intermediate cycling tour — led by Lisbon-based outfitter PortugalBike — seemed ideal for exploring a country I’d long wanted to visit. (And I’ll admit, 175 miles of cycling also meant that I could gorge on Portugal’s famous custard tarts all week long.)

That morning we’d set out from the town of Marvao, which, at 2,828 feet, boasts the region’s highest hilltop fortress. In addition to our enthusiastic guide, Jose Neves, I was riding with two other cyclists — John Reed of England and Werner Peeters of Belgium. With no experience on a road bike, I opted for the more stable hybrid bike, which made me much slower than the men.

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More on this Story

• Cycling across southern Portugal
• Details: Where to go, what to know in Portugal
• Photos: Discovering the Alentejo region

But no matter — Neves kept me in sight, and I fell into a steady pace as we pedaled down roads lined with cork trees. The rusty-red trunks had been stripped of their valuable bark, which takes about nine years to grow back before it can be harvested again. As I rode, I caught the sweet smell of wood smoke on the breeze, and the faint, almost musical jangling of farm animals’ bells echoing from the hills.

I could see why Neves said that cycling in a new country gives you “time to appreciate, to view, to notice the details, to smell, to listen.” What’s more, biking Portugal gets you more bang for your stride — unlike other cycling-friendly countries such as France and Italy, much of Portugal’s history, and even nature, is concentrated. “You only need to ride a kilometer to see many different things,” Neves told me.

When we arrived in Castelo (30 miles down!), I freshened up and headed for the castle’s stone tower. A winding staircase led me to a room with picture-frame views of the red-roofed village, which has been a revolving door for conquerors since the Romans took it in the 1st century B.C. The Moors invaded in the 7th century, and the Portuguese monarchy took over in the 12th.

But perhaps most interesting, Jewish refugees from Catholic-ruled Spain took refuge in Castelo in the 15th and 16th centuries. Today, the town has the oldest synagogue in Portugal, part of a small museum (regrettably, curated only in Portuguese). I wandered the steep paths of the Jewish quarter, admiring the arched Gothic doors and the marble-columned fountain with its purportedly healing waters. That night we dined at a local restaurant — specialty du jour, deer with chestnuts — and I took a liking to ginjinha, a sweet liqueur made from a type of sour cherry.

On Day 3, the landscape shifted from rocky lowlands to rolling vineyards and orchards, including olive, chestnut, pomegranate and orange trees. I often popped out of my bike clips to pick up a porcupine-prickly chestnut or taste a bitter olive plucked straight from the tree. Neves would also occasionally stop and give us mini-lectures on Portugal’s trees. Olive trees, for instance, live up to 260 years — “Older than your country,” he said to me with the equivalent of a wink in his voice. My favorite was a cork relative called azinheira, which reminded me of the African acacia and grows on hilly plains resembling the savanna.