A 387 km loop
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Scenery first, traffic last, with checkpoints that make sense on a bike. 387 km round from Milan - plan on about 7 h 02 of riding. The stops in between: Roasio and Aosta. The highest point is about 2,400 m. Much of it runs through woodland.
Milan does not try to charm you, and that is part of its charm. It is Italy's business capital, a city of fashion, finance and design that works hard and dresses well. At the centre stands the Duomo, a Gothic cathedral begun in 1386 and not finished for about five centuries, a forest of white marble spires and statues, and you can climb onto the roof among them. Beside it, the glass-roofed Galleria Vittorio Emanuele II is a nineteenth-century shopping arcade, and beyond it La Scala opera house.
In the refectory of Santa Maria delle Grazie, Leonardo da Vinci painted The Last Supper in the 1490s, and booking is essential if you want to see it. In the south, the Navigli canals, partly designed by Leonardo's era engineers, now line with bars and restaurants, and the city's aperitivo tradition, a drink with a spread of snacks, is at its best here. The yellow trams of the old city rattle along rails that are treacherous for motorbike wheels, especially in the wet.
South of the city lies the abbey of Chiaravalle, a Cistercian foundation from the twelfth century with a tall tower, standing in the fields at the edge of the suburbs, a peaceful contrast. The ride to the Venetian walls of Bergamo, built in the sixteenth century, leads north-east across the Lombard plain, where fog can hang thick in autumn and winter, then up into the foothills of the Alps. The roads are busy, so go early on a weekday, and be ready for a mix of motorway and small country roads.
Fuel is easy across the region, with plenty of stations on the ring roads, and bike parking is common in the centre, though the old core has traffic limits that you need to check. Try risotto alla milanese, golden with saffron, and ossobuco, braised veal shank, and finish with a slice of panettone, which comes from here. The city is quietest in August, when many locals leave for the sea, and liveliest in spring and autumn.
Roasio sits on the last low hills before the Alps, between Gattinara and Biella in northern Piedmont, a village of around two and a half thousand people spread across a few hamlets, with vineyards on the slopes above and the flat rice plain of Vercelli stretching south below. On clear days, Monte Rosa rises enormous and white to the north-west, and it is hard to concentrate on anything else.
This is a quiet wine corner with a great grape. The Nebbiolo, the variety behind Barolo and Barbaresco further south, is grown here too, on soils of porphyry and old volcanic rock, and the local wines, Bramaterra, Lessona and above all Gattinara, are elegant, firm and long-lived, though much less famous than their southern cousins. Roasio lies inside the Bramaterra zone, and the small producers in the area often sell from the door. In autumn, during the harvest, the lanes smell of crushed grapes.
The riding is excellent and still under the radar. The roads climbing north from the plain towards the Valsesia and the Biella hills are narrow and twisting, through chestnut woods, vineyards and small villages, with tight bends, short steep climbs and good views back over the plain. The surface is generally fair, with patches and gravel in places. Head west towards Biella and you reach the Ricetto di Candelo, a remarkable medieval fortified village built to store grain and wine, and beyond it the road climbs to the great sanctuary of Oropa in the mountains. Head east and you are soon in Gattinara, a town with a long main street, arcades and a tower on the hill above, the Torre delle Castelle, a landmark visible for miles.
Roasio has a fuel station and small shops, and if you need more, Gattinara is about six kilometres away, with supermarkets, bars, restaurants and wine shops. Coffee in a bar in the village is a simple pleasure, and you may find yourself chatting with old men who have farmed these hills all their lives.
The best times are spring, with wild cherry blossom and fresh green, and autumn, with gold and red leaves and the smell of wine. Summer can be hot and humid on the plain, with sudden thunderstorms in the afternoon, so ride early and keep an eye on the sky over the mountains.
Aosta is a Roman town with the Alps standing around it like a stage set. The Romans founded it in 25 BC as Augusta Praetoria, after subduing the local Salassi tribe, and they laid it out on a neat grid that still shapes the old centre. The Arch of Augustus, the Porta Praetoria gate, and the remains of a theatre with a surviving wall nearly twenty metres high stand among cafes and shops, and snow-capped peaks rise at the end of every street. It has been called the Rome of the Alps.
The reason for all this is the pass. The Great St Bernard, at about 2,470 metres, is one of the oldest crossings of the Alps, used by Celts, Romans, medieval pilgrims and, famously, by Napoleon's army in 1800. At the top, on the Swiss border, the hospice founded in the eleventh century by Bernard of Menthon has sheltered travellers ever since, and its monks kept the large rescue dogs that took the saint's name. The road from Aosta climbs the valley past old stone villages and the new tunnel entrance, then leaves the tunnel traffic to wind up through hairpins to the pass, with stone avalanche galleries and steep meadows. The old road is only open in summer, usually from June to October, and weather can bring snow even in July, so check conditions. Surface quality is generally good but narrow, with tight corners and occasional rough patches.
Valle d'Aosta is a small, autonomous region where French is an official language alongside Italian, and the food reflects the double heritage. Fontina, a soft, nutty cheese made from the milk of cows grazed on high pastures, is the signature, and it appears melted in fonduta, baked in soups and stuffed into cutlets. Local rye bread, cured lard from Arnad and sturdy red wines from steep terraced vineyards fill out the table. Castles crown many of the nearby hills, and those at Fénis and Aymavilles are especially fine.
Aosta is a town of thirty thousand with fuel, restaurants and hotels, and plenty of parking near the centre. Fill up here before heading into the mountains, because the stations get sparser the higher you go, and prices in Switzerland are higher. Carry your passport for the border and check whether you need a Swiss motorway vignette if you plan to continue on motorways. Warm clothes are a must for the pass, even on a sunny day.