A 186 km loop
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Scenery first, traffic last, with checkpoints that make sense on a bike. Out of Lisbon and back again: 186 km, roughly 3 h 23 in the saddle. Long stretches are under trees.
Lisbon is built on hills, as the old joke goes, to give the trams something to do. The city rises from the north bank of the Tagus river on seven hills, a tumble of tiled houses, church domes and steep cobbled lanes, with yellow trams creaking up the slopes, and the great red suspension bridge, the 25 de Abril, spanning the estuary. In 1755 a huge earthquake, followed by a tsunami and fires, destroyed much of the centre and killed tens of thousands, and the flat grid of the Baixa district was rebuilt afterwards under the Marquis of Pombal. The hill quarters of Alfama and Mouraria, which came through, still have their medieval twists and turns.
The city's character lies in small things. Fado, the melancholic music of longing, comes from cellars in Alfama and Bairro Alto, and the best places are small and quiet. Tiled walls cover buildings in blue, white and yellow. At Belém, just west of the centre, the Tower of Belém and the Jerónimos Monastery commemorate the age of exploration, when Portuguese ships sailed to India and Brazil, and a bakery nearby sells custard tarts, the pastéis de Belém, made to a recipe that is a close secret. Cod, grilled sardines and strong coffee fill the rest of the day.
The ride out of town toward the Atlantic is a favourite. The N247 follows the coast west from Cascais, passing Guincho beach, a windy surfing spot backed by dunes, and then reaching Cabo da Roca, the westernmost point of continental Europe, a cliff of about a hundred and forty metres above the ocean. Inland lies Sintra, with its palaces hidden in misty hills. Roads are generally good but busy, and the cobbled streets in town are very slippery when wet, so take care on tram tracks, which can catch a front tyre. Wind and sea fog are common on the coast.
Fuel is easy to find, though on the city's one-way streets finding parking can take time. Motorway tolls are electronic, so check how to pay if you plan to use them. Late spring and early autumn are the best seasons, and August brings crowds and heat.
Óbidos is a village in a box: a complete medieval walled town, whitewashed and flower-bordered, on a low hill over the plain. You enter through a gate decorated with blue and white tiles and then follow one long, steep street of cobbles to the castle at the top. The castle is now a hotel, which says something about how the Portuguese treat their history. The whole place is small enough to walk end to end in twenty minutes, and nearly all of it is pedestrian.
There is a charming story behind its status. In the thirteenth century King Dinis gave the town to his bride, Queen Isabel, as a wedding present, and for centuries afterward Óbidos belonged to the queens of Portugal. It was once a port, too, since the lagoon beside it, the Lagoa de Óbidos, used to reach much further inland before silt filled it in. Today the town is also known as a book town, with shelves in old churches and market buildings, and for ginjinha, a sour cherry liqueur drunk here from a small chocolate cup.
The riding to Óbidos is mostly gentle rural roads across farmland, orchards and low hills, with the long aqueduct and the walls of the old town appearing over a rise. It is a calm approach rather than a thrilling one, and the real action is on the coast, a few minutes west, where the road meets the Atlantic. In summer the town is crowded by midday with coaches, so the best time to see it is early in the morning or in the evening when day-trippers have gone and the stone turns warm. The cobbles inside the walls are slippery, particularly when wet, and a motorbike is best parked outside.
Óbidos itself has around eleven thousand residents across its municipality, and the nearby spa town of Caldas da Rainha, five kilometres away, is the larger place, with fuel, supermarkets and a ceramics tradition worth a look. Caldas was founded by another queen, Leonor, who built a hospital there beside hot springs in the fifteenth century. Back in Óbidos, find a table near the walls and try the cherry liqueur, though one is plenty if you are riding on.