The name has older versions: Winethereswick, Winriswic, Wenterswic. The Low Saxon suffix wich or wic meant simply the place where someone lived, the homestead of a man whose name might have been Wenether, Winitar or Winter. The settlement itself was founded around the year 1000, an isolated farming community whose isolation was the defining fact of its life until 1830, when the road from Borken in Germany to Zutphen in the Netherlands was finally pushed through. Some Winterswijk families have records going back to 1284. The Willinks are still here, more than seven hundred years after their first mention in the local archives.

Two things changed Winterswijk in the nineteenth century. The first was emigration. Around 1840, when poor harvests and crowded fields made the Achterhoek hard to live in, hundreds of families left for America, and a striking number of them settled in Michigan. Their descendants still hold reunions. The second was textiles. After 1870 the town became one of the eastern Netherlands' great cloth centers. The Tricot factory employed a large fraction of the population in its heyday. The local magnate Jan Willink, of the same family that had been in town since the thirteenth century, used his textile fortune to fund railways. The line from Winterswijk to Zutphen opened in 1878, built primarily to move the cloth that built the town. The mills are gone now. The rails remain.

Winterswijk was freed in the last weeks of the European war. On 30 March 1945, in the township of Woold just outside town, sixty Sherman tanks of the 53rd Welsh Division and the 3rd British Infantry Division clashed with German defenders. Sixteen Germans and nine British soldiers died in that single engagement. The next morning, about three miles south of Winterswijk, Allied forces fought through one more pocket of resistance reinforced by Dutch fascist militiamen of the NSB. By the late afternoon of 31 March, the first Allied troops reached the Slingestream at the edge of town. The town was liberated. Winterswijk's Jewish community had not been so lucky. The synagogue survived the war, but most of the people who had used it did not. It still stands, opened occasionally for visitors and guided tours, though regular services no longer take place.

Mondriaan is the famous one, but the list keeps going. Willem van Otterloo, born here in 1907, became one of the great Dutch conductors of the twentieth century. Max van Dam, born here in 1910, was an artist of striking promise who was murdered at the Sobibor extermination camp in 1943. Johanna Reiss, born in 1932, survived the war as a hidden Jewish child and later wrote about it from her adopted home in New York. The poet, novelist and critic Gerrit Komrij grew up here and became a defining voice of late twentieth-century Dutch letters. Dick Mol, born in 1955, is the world's leading specialist on mammoths and has identified fossils dredged from the North Sea floor. John H. Corscot left Winterswijk in the great Michigan migration and became mayor of Madison, Wisconsin, from 1893 to 1895.

The land around Winterswijk hides one of the most geologically interesting places in the Netherlands. A working quarry at the edge of town has cut through 240-million-year-old Muschelkalk sediments, exposing fossilized footprints of Triassic reptiles and ancient marine creatures. The wider region was admitted to the UNESCO Global Geoparks network as Geopark Achterhoek-Winterswijk. The town itself is small and walkable: the Jacobskerk on the Marktplein, the old town hall now serving as the tourist office, the brick water tower at the edge of town, the Strijktrio sculpture by Jan Bons that watches over the square. Around it all sit the small forests, streams and hedgerows that the boy Piet Mondriaan walked through before he learned to see them as rectangles.