Italian hit parade: A small town in Puglia comes alive for one of the world's oldest festivals

President Obama made his way towards me, grinning insanely and waving his arms. He was dressed, leprechaun-like, in a green suit and hat, and surrounded by dancers in glitzy outfits. Hundreds of cameras flashed from the crowd tightly packed along the parade route and people cheered and clapped as the great man approached.

As the 50ft papier-mâché effigy bore down upon me, I couldn't help but marvel at the ambition of this annual undertaking. Every year, Putignano, an otherwise unremarkable town of 30,000 people in the southern Italian region of Puglia, plays host to one of the oldest and longest carnivals in the world.

The carnival, which dates back to 1394, officially begins on Boxing Day and builds in the weeks leading up to the grand parade on the evening of Martedi Grasso (our Shrove Tuesday, which takes place on 16 February this year). During this period, barely a day passes that isn't marked by a traditional celebration of some kind, including three smaller, daytime parades on each of the Sundays before Lent.

Masked dances and outdoor concerts are held in honour of particular groups: Giovedi dei Pazzi ("Thursday of the mad") is for single people, while Giovedi dei Cornuti celebrates, or rather sympathises with, the cuckolded.

It's cold at this time of the year in Putignano, but that doesn't stop tens of thousands of people from the surrounding area donning brightly coloured wigs, painting their faces and lining the cobbled streets of the centro storico to celebrate the last night of fun before Lent begins.

There are plenty of other attractions nearby as well: Ostuni, a medieval hill town about an hour's drive away, is known as La Città Bianca (the White City) for its brilliantly whitewashed buildings. I spent a lazy afternoon strolling the labyrinthine streets of the old town, warming up with cocktails and live jazz at Caffè Cavour, a bar featuring an underground cave interior converted from a 12th-century oil mill.

Lying about halfway between Ostuni and Putignano is Alberobello, a town celebrated for its trulli: traditional Pugliese cone-roofed dwellings designed to be easy to build and dismantle. Legend has it that when tax inspectors came by the little houses would be taken to pieces, leaving nothing worth taxing.

The parade, though, is the highlight. Last year, I arrived by car and was ushered into a makeshift car park on the outskirts of the old town and asked to pay €5 for the privilege by a decidedly unofficial-looking character. A short walk later I found myself in the middle of what was effectively one enormous passeggiata, as extended families strolled around together in their fancy dress and finery in the hours before the parade began.

Stalls selling mountains of pick'n'mix sweets and clouds of candyfloss proved impossible to resist as I made my way through the crowds on the lookout for the perfect spot from which to watch the parade.

The aroma of porchetta – roast pork flavoured with herbs and garlic – wafted through the night. Slices of this traditional street food were loaded into panini and served hot to the chilly crowd (along with plastic cups of surprisingly palatable red wine, which cost just 50 cents). The action was supposed to start at 7pm, but it didn't get going until 9.30pm, meaning there was plenty of time to sample what was on offer.

The parade began with bands, street entertainers and groups of revellers in elaborate fancy dress, including some in costumes in the shape of trulli; and a walking celebration of local cuisine featuring costumes made of tables laden with whole dinner services. They were followed by hundreds of small children wearing mildly offensive costumes based on the traditional dress of cultures from around the world (including a troop of six-year-olds in brown body-stockings and grass skirts representing Africa).

Finally, the carnival's star attractions appeared, making their way slowly down the parade route: gigantic papier-mâché floats built from scratch every year by competing teams of craftsmen. They had been constructed in the preceding four months – the last few weeks of which were spent working practically around the clock. These allegorical creations range in theme from economics to politics, depending on the inspiration of the master cartapestaio (papier-mâché artist) and are all on a scale that has to be seen to be believed.

The winner of the much sought-after Primo Premio, with prize money of over €22,000, is announced to a crowd of ecstatic revellers in Putignano's freezing main square at the culmination of the parade.

Last year's winner was an enormous Noah's Ark filled with animals representing members of the Italian parliament. It was satirising the corruption in the nation's politics that allows the lawmakers to reap huge financial rewards through backhanders and tax privileges: the idea being that these individuals are the chosen few, and everyone else drowns in the flood of recession.

This was master cartapestaio Deni Bianco's third consecutive win and only the fourth year the 34-year-old had entered the competition with his own team. The longest-serving master craftsman, Franco Giotta, who in 2009 entered with a float satirising the economic chaos since joining the euro, has been competing for over 50 years, winning the Primo Premio 22 times; Deni Bianco has a long and illustrious career ahead of him.

Travel essentials: Puglia

*Ryanair (0871 246 0000; ryanair.com ) flies from Stansted to Bari and Brindisi, which are 50 and 70 minutes' drive from Putignano respectively.

*Caffè Cavour, Ostuni (00 39 0831 301 709).

*Puglia Tourist Office: viaggiareinpuglia.it