Discover Serra da Estrela: Medieval Towns, Craft Beer, and Secret Swimming Spots

The centuries-old villages of the Serra da Estrela, in Portugal’s Centro region, provide an evocative road trip experience. Kieran Dahl immerses himself in the magic of the mountains.

After driving up to the summit of Torre, the highest peak in Portugal’s Serra da Estrela mountain range, I felt a childlike urge to climb even closer to the clouds. I spotted a narrow concrete plinth and hoisted myself onto it. Finding my balance, I raised my arms shakily in triumph. “Do you realize,” I called down to my girlfriend, Diana, “that I’m higher up than every single person in continental Portugal?”

Diana rolled her eyes, unimpressed. Never mind that we’d driven up a long, winding road to Torre’s summit. She had been skeptical of my idea to head straight for the mountains. This was, after all, a country shaped by the Atlantic Ocean, featuring coastal cities, balmy beaches, and seafood aplenty. However, I felt vindicated.

All that driving and climbing had left us famished, so we scoured the Centro Comercial da Torre (351-911-546-037), a cramped general store filled with cured meats, sheepskin-lined clothes, liqueurs, and local dairy products. I purchased a loaf of bread, a chunk of tangy cheese, and two seven-ounce bottles of Super Bock, the unofficial beer of Portugal.

Outside the store, sitting on its sweeping back deck, we could hear the skeletal chairlift of the country’s only ski resort idly twisting in the wind until next winter. The aging towers of an abandoned observatory glinted in the summer sun. We enjoyed our peaceful picnic while gazing at the dramatic landscape of the Serra da Estrela.

That morning, we’d driven nearly three hours south from Porto through the Centro region, which stretches across the heart of Portugal from the Atlantic Ocean to Spain. Our objective was to explore the rugged environs of the Serra da Estrela and appreciate the area’s rich history.

In the 1600s and 1700s, the Portuguese-Spanish border was a fiercely contested battleground. Settlements transformed into fortified villages, strategically located on hilltops, with some dating back to the 12th century. Today, 12 of these towns comprise a government-designated network known as the Historical Villages of Portugal.

We hadn’t anticipated white-knuckle driving as part of our adventure. With me behind the wheel and Diana in the passenger seat, we drove 45 minutes down the zigzagging road from Torre, stopping at a 25-foot bas-relief sculpture carved into the side of a mountain. The artwork depicts Senhora da Boa Estrela, the protector saint of shepherds. We parked on the roadside and climbed a small set of stairs to the statue’s base, looking up in awe at the two-story saint.

Our final destination that day was Belmonte, a city of 7,000 built around a Roman-era castle. We checked into the Pousada Convento de Belmonte, a 13th-century monastery transformed into an elegant hotel. The building’s ecclesiastical past exuded weighty stillness. The living room had once served as a chapel, still retaining its vaulted ceiling. Diana and I spoke in hushed tones, akin to being back in Sunday school, and slept soundly in our serene bedroom. In the morning, we admired the sunrise over the jagged peaks of the Serra da Estrela from the stone-lined swimming pool.

Revitalized, we resumed our journey toward the castle, passing houses adorned with flowering window boxes. Little remains of Belmonte’s castle, consisting of just the exterior walls and two crumbling towers. From its ornately carved window, which overlooks the green shades of the Zêzere valley, I tried to picture the medieval past, envisioning the armored knights who once protected the structure. We proceeded to Torre de Centum Cellas, a dilapidated structure from the Roman period. Historians remain uncertain whether it served as a temple, a prison, a villa, or something else entirely. Its open-air ruins resembled a crown, with battlements silhouetted against the purple sky.

In the early evening, we set out for the Quinta da Barroquinha, a charming cottage situated on a seven-acre farm near Vale de Prazeres, ideal for our next two-night stay. The cottage, once a shepherd’s hut, still displayed rough stone walls and a woodstove reflecting its past. After our host welcomed us with a small bottle of locally made olive oil, Diana and I cooked pasta and shared a bottle of Portuguese red on the patio. As we dined, the scattered valley lights gave way to a starry night.

After breakfast the next morning in Alpedrinha—by now, “pastéis de nata” and “café, por favor” had become our daily refrain—we drove up a rocky hill to Monsanto, a village built beneath, between, and atop gigantic granite boulders. The narrow cobblestoned lanes were inaccessible to cars, leading us to walk through the streets while marveling at the stone walls. One house had a roof formed by a globular mass of granite. On either side of another property, boulders compressed it like a corset. One home even had its entrance carved directly into the rock, featuring a low-slung wooden door.

From the impressively preserved ramparts of the castle crowning Monsanto, we could see for miles. Birds floated on the wind at our eye level; the sun was strong overhead, causing beads of sweat to form on our foreheads. Seeking refuge from the heat, we hastily made our way downhill to the cozy Taverna Lusitana. We sat at a tiny minuscule table on its terrace, with carved-out boulder seats, and shared a pizza alongside beers from the taverna’s own brand, Cerveja de Guerreiros. The refreshing mugs soothed our sunburned faces. In the corner of the terrace, an artist sketched the valley, capturing the landscape’s essence along with the village’s barrocais, or “chaos of blocks,” that shape many old towns in the region.

Following our visit to Monsanto, we explored Castelo Branco, a Templar stronghold dating back to the early 1200s. Remnants of its castle consist of a wall and two crumbling towers. The verdant garden, Jardim do Paco Episcopa, infused the experience with vibrant life. As we wandered through the maze of waist-high hedges, we were serenaded by the delicate trickling of fountains, imagining the lives of the first inhabitants.

A short drive away, we arrived at the remote village of Penha Garcia, where a well-worn path led us to the highest point in town. From there, signs guided us on a two-mile tour through a series of narrow streets.

We passed old mills, rocks containing fossils that locals called “painted snakes,” and a natural pool. Lacking bathing suits and towels, the water’s alluring, blue-green tint felt like a mirage. However, looking at the map, we discovered a more secluded body of water, a man-made reservoir surrounded by an empty beach.

A bumpy off-road drive put our rental car to the test, ultimately leading us to this tranquil spot. Alone except for the rustling pine trees, we decided to skinny-dip in the placid pool. While I swam in lazy circles, Diana retreated to the shore to enjoy cheese and smoked sausage. When I looked back at her, she held a large lemon she’d plucked from a tree, as round and large as an apple. The past felt tangible here, on a remote edge of Portugal, in the shadow of an ancient castle.