Venlo is mentioned in 9th-century documents as a trade post on the Meuse, halfway up the river between the heartland and the sea. It got city rights in 1343 and joined the Hanseatic League in 1375, an alliance more often associated with northern German ports than with a Dutch border town. Its strategic position made it a target for siege after siege; the most consequential was the assault of 1702, led by the great Dutch military engineer Menno van Coehoorn, after which Venlo passed into the Generaliteitslanden of the Dutch Republic. From 1839 to 1866 the city occupied a geopolitical curiosity, lying outside the German Confederation while completely surrounded by it, an island of Dutch sovereignty inside a German sea.

Between 13 October and 19 November 1944, Allied air forces tried thirteen times to destroy Venlo's road and rail bridges over the Meuse. Every attempt failed. Cutting the bridges would have severed German supply lines and trapped the retreating Wehrmacht on the wrong side of the river. The raids killed about 300 people in Venlo, leveled much of the medieval city, and never quite hit the bridges. In the end, the retreating Germans themselves blew them up to slow the Allied advance. The destruction was so thorough that the city center had to be rebuilt almost from scratch in the 1950s. A few survivors, the Stadhuis and the Romer house among them, still hint at what was lost. The city also lost its small Jewish community in the Holocaust; the prewar population had grown to around 248 as German Jews fled across the border, but only 32 remained by 1951.

By the late 1990s, Venlo's city center had a drug problem. The Q-4 Project and the Tango initiative pushed the largest coffeeshops to the outskirts, where they still operate, and the historic center quieted down. The pivot worked. In 2003, Venlo was named the Greenest City of Europe. In 2012 it hosted Floriade, the world's largest horticultural exhibition, which is held once every ten years. In 2013, the city won Best City Centre of the Netherlands on the strength of investments in the Maas Boulevard, a rebuilt railway station, and a central traffic tunnel. The reinvention is not subtle. Where bombs once fell on bridges, manicured public squares now host bands during Zomerparkfeest, the four-day August festival that occupies the city's main park.

Modern Venlo runs on logistics, horticulture, and quietly important corporate addresses. The printing-equipment giant Oce, now part of Canon, is headquartered here. So is Cimpress, the parent company of Vistaprint. Amway's European headquarters sits in Venlo, as does Office Depot's continental office, and in 2017 the international online retailer vidaXL moved its headquarters and massive warehouse here. The reason is geography. Two German autobahns, the A40 and A61, put Dusseldorf, Duisburg, Cologne, and the Ruhr within an hour. Greenport Venlo, one of the Netherlands' five designated horticultural clusters, links across the German border into the Niederrhein agro-belt; together they form Europe's largest horticultural region, feeding a market of roughly 30 million people.

Venlo's signature festival is not Floriade or Zomerparkfeest but Vastelaovend, the local form of Carnival celebrated six weeks before Easter. The streets fill with costumes, brass bands, and a dialect that is its own argument against Dutch standardization. The city's football club, VVV-Venlo, has played at De Koel Stadium since the early days of professional Dutch football and continues to bounce between the Eredivisie and the Eerste Divisie with cheerful unreliability. The city has also produced a notable run of public figures, from the polarizing politician Geert Wilders, born here in 1963, to the actress Chantal Janzen and the Renaissance painter Hubert Goltzius. The Maaspoort theater, the Limburg Museum, and the Museum van Bommel van Dam fill out the cultural calendar. The cafes along the rebuilt boulevard look out over the same river that once carried Hanseatic cargo and Allied bombs, and the bridges, finally, have been rebuilt for good.