Portillo

The road climbs through wheat and pine until the plains suddenly drop away. At 850 metres, Portillo’s stone walls appear like a ship’s prow above the meseta, the castle keep catching the late-afternoon light exactly as it did when medieval scouts scanned for Moorish raiders. Inside the single-lane gate, tyre-width stripes of whitewash warn unwary drivers: wing mirrors have died here. Park on Calle Ronda, leave the car, and the town’s 500 souls get on with life at their own unhurried cadence.

A castle for 45 minutes, views for the rest of the day

Entry is €4, cash only, and the custodian prefers exact coins. Expect a forty-five-minute circuit: spiral stairs to the battlements, roof-top 360° over ochre fields, a single vaulted room with a dusty display of chain mail. Then the place is yours to sit on, lean against, photograph from every angle. In April the storks clatter overhead; in October the stone glows tobacco-brown. Arrive before 11:00 or after 17:00 and you’ll share the ramparts only with swifts and the occasional Spanish couple from Valladolid doing the same thing.

Below the walls, the town tumbles down a knob of rock. Streets are barely two metres wide, paved with river pebbles polished to glass by centuries of hooves and, more recently, Seat Ibizas. House doors open straight onto the gradient; grander mansions squeeze coats of arms above the lintel, some freshly repainted, others blurred by frost and forgetfulness. Laundry flaps from wrought-iron balconies, and the smell of pine resin drifts up from the Sierra de la Paramera somewhere beyond the horizon.

Plaza life and Tuesday cheese

Plaza de España is the living-room. Elderly men occupy the same bench every morning; the bar on the corner pulls cortados at 70 cents and will refill your water bottle without fuss. Tuesday is market day: three stalls, one of them selling nothing but local queso de oveja—firm, nutty, half the price of Manchego in Borough Market. Buy a wedge, add a loaf from the bakery on Calle San Pedro, and you have picnic rations for the pinewalks later.

The sixteenth-century church of Santa María closes between 13:30 and 17:00, Spanish lunchtime being sacred. When the doors reopen, step inside for a hybrid Gothic-Renaissance retablo and, if you're lucky, a pensioner who will switch on the lights for a euro tip. Portillo never feels like an open-air museum; it feels like someone’s aunt has stepped out to water the geraniums.

Walking without the sweat

You don’t come here for alpine thrills. You come for horizontal miles under a huge sky, broken by the soft roll of cereal fields and the occasional granite outcrop. The Cañada Real Leonesa, an ancient cattle highway, skirts the town; follow it south-east and within twenty minutes the tarmac gives way to a sandy track scented with thyme and resin. Forty-five minutes farther is a stone shepherd’s hut—roof gone, walls shoulder-high—perfect for that cheese sandwich. Turn back when you’ve had enough; the trail is way-marked by painted dashes on pine trunks, though mobile signal is patchy, so screenshot the route on Google Maps before you set out.

Mountain-bikers use the same web of lanes. Gradient is gentle but the wind can be spiteful; what looks flat on the profile feels like a false flat into a hair-dryer when the levante decides to blow. Pack a gilet even in May.

Roast lamb and early nights

Food is meat, beans, more meat. Restaurante Foodsion (Calle Castillo 7) does a half-ration of cordero asado for €14—enough for two if you add judiones, the local butter-bean stew the size of conkers. House red from Rueda is served in plain glasses, no tasting notes required. Vegetarians get tortilla or salad; don’t expect quinoa. Kitchens stop taking orders around 21:30, and by 22:15 the square is quiet enough to hear the castle flagpole rope clanking against the mast.

Getting there, getting out

Fly to Madrid, pick up a hire car at Terminal 1, and you’re on the A-50 within ten minutes. Two hours later the sat-nav loses its nerve as the road narrows to a single track; you’re close. There is no petrol station in town—fill up in Arévalo, ten kilometres back. Buses from Madrid exist but involve a change in Valladolid and a timetable that treats weekdays and Saturdays as optional; by the time you arrive you could have driven to Santiago.

Stay the night or press on? Segovia’s aqueduct is 55 minutes west, Ávila’s walls roughly the same north-west. Chain hotels cluster beside the A-50, yet Portillo itself offers two small guesthouses—Casa Rural El Castillo and La Casa del Tío Valentín—both under €70 for a double, both spotless, both with owners who speak fluent gesture. Breakfast is coffee, toast and tomato; ask for mantequilla if you miss butter.

The honest verdict

Portillo will not change your life. It will give you a castle you can photograph without tourists photo-bombing, a plate of lamb you’ll still remember in a Derbyshire pub months later, and a reminder that rural Spain is neither theme park nor hardship post—just everyday life happening at altitude. Come for the slow roads, the roof-top wind, the Tuesday cheese. Leave before you start recognising the dogs by name; the place deserves its anonymity, and the drive back to Madrid is prettier at sunset anyway.