Winschoten received city rights in 1825, the last municipality in the Netherlands ever to do so. By that point the designation was largely ceremonial — a courtesy paid to a town that had quietly become the commercial center of the Oldambt district. The flag, adopted by municipal resolution on 23 May 1973, shows three horizontal blue-and-white stripes with a red outline of a fortress in the middle, nine embattlements wide. The coat of arms depicts Saint Vitus, whose name turns up everywhere in town — on schools, sports clubs, the Catholic parish that Alfred Tepe built in neo-Gothic brick in 1880. The high altar inside that church traveled from a demolished church in Nieuwe Pekela. Winschoten is in the habit of inheriting things from places that have closed.

In the early eighteenth century thirteen windmills stood inside Winschoten's town boundary, enough that locals called the place Molenstad — Milltown. Three remain. Molen Edens at Nassaustraat 14 is the oldest mill anywhere in the province of Groningen, built in 1763 on the instructions of Jurrien Balles and Antje Gerbrands. Molen Berg on the Grintweg, raised in 1854 by J.D. Buurma to grind grain, was unusual for its time — its sails carried movable blades like venetian blinds instead of the traditional canvas. Molen Dijkstra on the same Nassaustraat went up in 1862 and stayed in the Dijkstra family until 1953. All three are now owned by the municipality and operated by volunteer millers on Saturdays. The other ten came down quietly during the industrial revolution. Steam was faster. Diesel was cheaper. A windmill is a poor competitor in a market that does not care about wind.

The town acquired two unflattering nicknames over the centuries. One, mentioned earlier, was Sodom — apparently coined by Jewish residents shocked by the drinking and revelry they observed among Gentile neighbors. The other, tellerlikkers, plate lickers, allegedly came from the local custom of devouring meals so completely that the dish itself needed cleaning. A bronze statue on Oldambt Square commemorates this — a man at table, plate raised, dog finishing his shoes. Both nicknames are still in use, though Sodom now appears mostly in local-history columns. Tellerlikker, by contrast, is something people in Winschoten still call themselves, half-mockingly, the way Bostonians call themselves Bean-eaters. Self-deprecation outlasts almost everything else in a small town's vocabulary.

During the Second World War, Winschoten was used as a transit point for the deportation of Jews from northern Netherlands across the German border. The trains east left the railway station that had opened in 1868 to serve the Groningen–Winschoten–Nieuweschans line. Of the 493 Jewish inhabitants registered before the war, only twenty returned. The Jewish school, the synagogue, the kosher butcher — all the institutions that had given the town its Yiddish-tinged dialect — disappeared in those years. What remained was the language itself, words like sjoel (synagogue) and gabber (friend) folded into Gronings and used now by speakers who do not always know where the words came from. The cemetery on the edge of town is one of the few physical traces left. The dialect is the other.

Every September, on the second Saturday of the month, Winschoten hosts De RUN — the oldest ultramarathon in the Netherlands, founded in 1976. The course is a ten-kilometer paved lap repeated ten times through the town. The standing 100 km record, set by the Belgian ultrarunner Jean-Paul Praet in 1992, is 6:16:41 and has held for more than three decades. Runners who do not want the full hundred can enter a 50 km variant or a ten-by-ten relay. For one Saturday a year, a town better known for shopping and ageing demographics becomes a place where strangers in lycra circle the windmills and the church and the plate-licker statue, hour after hour, until darkness or success ends the day.