Madeira in September 2026: The Festivals Worth Planning Around
September is grape harvest season on Madeira, and the island's festival calendar reflects it — wine events run almost every week. But it's also one of the busiest months for patron saint festivals, with several of the island's largest religious celebrations landing in September.
Madeira Wine Festival (continues)
The island's main wine festival, which started in late August, runs through 13 September. The Madeira Wine Lounge in Funchal's Praça do Povo continues with tastings, food, and live music, while the Estreito de Câmara de Lobos leg — live grape picking, a pickers' parade, and grape treading — is the more hands-on part of the festival throughout the month.
Columbus Festival — Porto Santo
A week-long festival on Porto Santo built around Christopher Columbus's historical ties to the island — he lived there in the 1480s, and his first child was born on Porto Santo. Held in Vila Baleira, it includes music, exhibitions, parades, and street parties, with a re-enactment of Columbus's arrival in the harbour as the highlight.
Trans Madeira
A five-day enduro mountain bike race that crosses the island from north to south and east to west, running from late September into early October. Competitors — capped at 120 — cover around 200km across 25 stages, climbing roughly 2,300m a day.
Grape and Farmer Festival — Porto da Cruz
A harvest festival in Porto da Cruz, a town known for its dry red wine (vinho seco). Features a parade with folklore groups, traditional costumes, decorated floats, and a look at historic winemaking equipment, alongside wine tastings.
Apple Festival — Ponta do Pargo
A harvest festival in the rural village of Ponta do Pargo, built around the region's apples — well-regarded enough to have been mentioned by regional writers for their aroma. Includes the usual food and drink stalls and draws visitors from neighbouring parishes.
Apple Cider Festival (Mostra da Sidra) — Santo da Serra
A festival celebrating Santo da Serra's tradition of apple cider making, with a small procession, a demonstration of the apple pressing process, and music and activities built around the harvest theme.
Harvest Festival — Quinta do Furão
An annual wine harvest event at Quinta do Furão in Santana, with hands-on activities including grape picking, winemaking, and tastings.
Classic Car Race — Caminho dos Pretos (Monte)
A classic car race along one of the region's most scenic routes, through the Monte parish above Funchal, known for its speed trials and a closing awards banquet for participants.
L Concerts (Concertos L)
A recurring concert series at Estalagem da Ponta do Sol, with four dates in September. The lineup spans rock, jazz, indie, and traditional music, performed by local, national, and international artists in a clifftop setting over the Atlantic.
Faial Festival (Festa do Faial) — Santana
A patron saint festival honouring Our Lady of the Nativity in Faial parish, combining a religious procession with national and regional musical acts, traditional Madeiran food, street festivities, and a fireworks display.
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Your Madeira Guide