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.
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.
Eventually an imposing, 102-foot-high aqueduct popped onto the horizon, announcing our arrival in the next medieval village: Elvas. Surprisingly, the 4.5-mile-long structure — which still brings water to the city — is not a Roman remnant, but was built by royalty in the 1400s. We checked into our lodging — a cavernous 17th-century military hospital — and made it to the well-preserved castle just before closing.
Elvas’s history seemed to mirror Castelo’s — the Romans came here first, then the Moors, then Portugal’s first king, Afonso Henriques, took over in 1166. Nudged against what’s now the Spanish border, the twice-walled town was also built with defense in mind. Inside the castletower, Neves pointed out the vertical slits through which soldiers once flung arrows at invaders.
I walked the cool, empty rooms and narrow passageways connecting the turrets, trying to imagine the royal dramas that had taken place here over the centuries: the 1382 peace treaty between Portugal and the neighboring Spanish kingdom of Castile, the wedding of future king Joao IV to Luisa de Gusmao in 1633, the reception for Philip II of Spain when he was crowned king of Portugal in 1581.
The next day we entered marble country, stopping for lunch in Vila Vicosa — a marble-producing town that was a hub for the Dukes of Braganza, one of the most esteemed houses of Portuguese nobility in the 15th century. Cristina Henriques, co-owner of PortugalBike and Neves’s wife, prepared us another scrumptious picnic — a daily lunch is included with the guided tour — with delicacies such as local sheep cheese and homemade hazelnut cake.
Touring the city afterward, it seemed to me that pretty much everything in Vila is made of marble, from lampposts to the slate-blue 16th-century Ducal Palace. I was disappointed that we didn’t tour it, instead visiting a marble museum. But the day’s highlight was walking our bikes right into a working marble quarry, our skintight shorts attracting a few curious looks. We peered over the edge of the 250-foot chasm as the machines broke apart slabs that will later be shipped all over the world.


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A walk across the Scottish Highlands

The stone obelisk and huge banner that marked the start of the trail would have been obvious on their own, but the dozens of backpackers surrounding them made them impossible to miss. I’d been told that the West Highland Way was the world’s most popular hiking trail. And suddenly, I believed it.

I’d set out to walk the 169 miles from the suburbs of Glasgow to the city of Inverness, across the West Highlands of Scotland. With two of the biggest lakes and some of the wildest country in Europe, it was a hike that seemed right for someone with two or three weeks to spend on the trail.
My route might have been long, but it was clearly marked and well documented. Starting in suburban Milngavie, I would walk the West Highland Way 96 miles to the town of Fort William. There, I’d pick up the Great Glen Way for the final 73 miles to Inverness. I planned to cover 10 to 12 miles a day.
The first mile was a paved path with streetlights; you could follow it night or day, fair weather or foul. Soon, though, the streetlights stopped, the pavement became gravel, and then the gravel became dirt. It was the same for trail markers; the first was that stone obelisk. But a few miles farther on, the markers became fewer, and as the afternoon rolled by, they pretty much faded to small, stylized arrows on wooden posts. It wasn’t a problem, though. All I really needed to do was to follow the bootprints. There were seemingly hundreds of them.
Though the West Highland Way is a footpath, it’s not always a wilderness trail. In fact, my first stop was the Glencoe Distillery. Entering the crowded tasting room with my backpack, I was given a free shot of whisky. And later in the day — after miles of walking through pastures filled with grazing livestock — I had a slice of chocolate cake at a trail-side tea shop.
On stretches like these, you don’t just barge across fields and through herds of animals; instead, you have to open and shut gates and follow the marked and well-trod way across whatever landscape it leads you through.
This British walking is as addictive as crack cocaine: the cool, soothing air; stops at rural pubs and tea shops; hostels filled with backpack-bearing hikers; B&B rooms with a candy bar left as a gift for you; and footpaths that bring you in close touch with mountains, lakes, fields and villages. Walking in Great Britain always has an upside; a rainy day on a Scottish trail is better than a sunny day at your desk. You don’t have to camp (although many people do), so you don’t have to lug around any camping gear. And if you’re still lugging too much, popular trails like these have bag-carrying services that will move your pack from place to place for you.

For the first night, I’d reserved a room at a bed-and-breakfast inn near the town of Drymen. It was classically British: clean, with a hot shower and, on top of the dresser, my own private kettle with tea bags, instant hot chocolate and milk. Breakfast the next morning was the “full Scottish,” with eggs, black pudding, potato scone, cooked tomato and toast. It was so huge that it nearly put me right back to sleep.
After another day of agriculture, pastures full of sheep, managed tree farms and fields of heather, the trail reached Loch Lomond, hugging the lake’s shore for more than 20 miles. Scrambling over rocks and roots, spending one night in a hostel bunk and another in a luxury hotel (with a plastic tray in my room for muddy boots), I made my way past Britain’s largest lake and was soon climbing into the mountains and wishing that the trail would make up its mind about how challenging it was going to be.
Sometimes, it would be level and well graded for a mile or two, then shoot almost straight up. Or maybe it would run through fields of grazing animals, then suddenly enter a forest. A mile of gravel could easily become mud, and there were those moments when you’d think that somebody had artfully surfaced the footway with manure.
I was never alone on the trail. Hikers from every corner of the world were on it with me, and by the end of the first week, I’d come to know quite a few of them. Margret, an Australian doctor, was impeccably fit and had hiked all over the world, while two Dutch sailors with cheap gear and no preparation managed to keep up, offering explanations such as, “We don’t need water bottles, we take all our hydration in the form of beer in the evenings.” This, of course, horrified the doctor.
Sometimes, I’d see somebody once and never again. And then there were the people who wound up in the same pubs, shops and even hostel bunkrooms as I did, day after day. We were an ad hoc caravan making our way across the countryside.
There was always a fairly wide assortment of accommodations available. Backpackers’ hostels are cheap, cramped and cheerful. Official Scottish Youth Hostel Association hostels are a bit more spacious (but still reasonably priced), bed-and-breakfast inns are the most common, and luxury hotels are an occasional treat.
Few small-town overnights were as interesting as the one I spent at Bridge of Orchy. The village is well-named; it has a pub, a train station, an informal campground — and the bridge. Those seeking a bed have the choice of a hostel in the train station, lodging at the pub or a historic hotel. I chose the train station; meals were served in the ticket office, and the coed bunkroom was done up like an old European sleeping car, with a built-in reading light and curtains for each bed. As is typical at hiker hostels around the world, we thought we were staying up late talking gear and comparing blisters, but actually everybody was asleep before 10.

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