The first mention of Jews having lived in Winterswijk dates to 1700. The Jewish population of Winterswijk grew over the course of the 18th century; an organized Jewish community, however, did not come into existence in the town until the century drew to a close. The community was officially recognized in 1800.

During the early years of Jewish life in Winterswijk, religious services were held in synagogues in private homes at various locations in the town. In 1847, an actual synagogue building was consecrated in the Jodensteeg (Jews' Alley). The Jodensteeg synagogue remained in service until 1889 when it was converted to house Winterswijk's Jewish school following the consecration of a new synagogue in the Spoorstraat.

Prentbriefkaart van de synagoge met school in Winterswijk, ca. 1914

Postcard of the synagogue and school in Winterswijk, ca. 1914

During the second half of the 19th century, the Jewish population of Winterswijk grew rapidly. At the time, Jews in Winterswijk worked mainly in the textile trade, the livestock trade, and the meat industry. Jews were also active in society at large; a Jew served as interim mayor of Winterswijk during the early 20th century and, in 1919, a Jewish socialist was elected to the town council.

The earliest known Jewish cemetery in Winterswijk was established in the 18th century and was probably located on the Kottenseweg near the Elinkbosje. A second Jewish cemetery, located in the Spoorstraat, was opened at the close of the 18th century and remained in use until 1884 when the present-day Jewish cemetery in the Misterweg was opened. A temporary split in the community during the 1870s resulted in the opening of a small Jewish cemetery near the Venemans Molen.

The Jewish community at Winterswijk was governed by a community board and community council. The Board also administered aid to the poor. Other community officials included a treasurer for collecting and disbursing aid to the Jewish community in Eretz Israel. The Jews of Winterswijk also maintained a number of religious, social, and cultural voluntary organizations. In the years around 1920, several Jewish pioneers preparing for emigration to Palestine trained in the vicinity of Winterswijk. Winterswijk absorbed many Jewish refugees from Germany during the 1930s.

During the World War II German occupation of the Netherlands, the Jews of Winterswijk suffered under the same measures as Jews elsewhere in the Netherlands. In September 1941, following the exclusion of Jewish children from public education, an elementary school for the Jewish children of the region was established at Winterswijk. The school remained in operation until April, 1943. Arrests of Jews in Winterswijk began as early as October, 1941. Deportations from Winterswijk to Nazi death camps via the transit camp at Westerbork began in earnest in November 1942 and continued until April 1943.

The majority of the Jews of Winterswijk were murdered during the war; only a small number returned alive from the camps at the end of the war. A few local Jews managed to survive the war in hiding, most with the help of the Landelijke Organisatie voor Hulp aan Onderduikers (National Organization for Aiding Those in Hiding). The synagogue at Winterswijk was plundered during the war; its interior was destroyed and the building was converted into a gym. The synagogue's Torah scrolls were removed from the building early in the course of the war and were hidden and later recovered.

Jewish life was reestablished in Winterswijk soon after the war ended. The synagogue was restored and its interior was refurnished with accouterments and ceremonial objects from the synagogues of other former Jewish communities in the Netherlands. The Winterswijk synagogue was officially reconsecrated in 1951. A second restoration of the synagogue took place between 1982 and 1984. At present, the synagogue is occasionally open for religious services. The two Jewish cemeteries at Winterswijk are maintained by the local authorities.

A monument in the Jewish cemetery on the Misterweg is inscribed with the names of Jews from Winterswijk deported and murdered during the war. A second monument to the memory of the Jews of Winterswijk was unveiled in 2002 on the Mevr. Kuipers-Rietbergplein is just across from Winterswijk's town hall.

The Jewish population of Winterswijk and surroundings:

The size of the Jewish community over time