The earliest mentions of the Jewish presence in Grajewo date back to 1676. The poll census carried out that year recorded two Jews and their wives among the 35 people living in the town. Towards the end of the 18th century, the Jewish population already formed a subkehilla subordinate to the community in Rajgród.

Historical records from 1800 mention a large Jewish community based in Grajewo – there were 168 Jews among 218 of the town’s inhabitants. The local synagogue supervision was established in 1826, and in 1839, the community already had its own rabbi. Grajewo experienced a mass influx of Jews after the opening of a paved road connecting Warsaw with Petersburg. In 1857, there were 1,459 Jews living in the town, which had a total population of 1,917.

The community continued to develop thanks to the town’s location and its function as a border crossing with Prussia, making use of the central Brzesko-Grajewska rail line connecting the Baltic Sea and the Black Sea. At the turn of the 20th century, the Jewish community constituted the largest percentage of the total population in its history, reaching 70%. Jews mostly made a living from trade, crafts, and small-scale production (rubber products, building materials, mills, distilleries). Nonetheless, the community was rather poor, especially after the tragic fire of 1886, which consumed almost all of the town’s buildings.

The same period was also marked by thriving cultural and social life in the town, both on the part of the Orthodox Jews (who were the dominant force in the local community) and the Progressive and Zionist circles. A branch of Hovevei Zion was founded in Grajewo in 1886. A Hebrew elementary school was opened ca. 1900. There was also a cheder headed by activist Abraham Mordechai Fiorke, who also published a Hebrew-language magazine for children. Zionism was supported by both rabbis serving in Grajewo at the turn of the 20th century. Elijachu Aharon Miłkowski, who assumed the post in 1892, later became the head of a religious court in Tel Aviv. His successor since 1913, Mosze Awigdor Amiel, also eventually migrated to Palestine; before becoming the rabbi of Tel Aviv, he worked in Antwerp. The Bund opened its Grajewo branch in 1902.

For the community of Grajewo and many other Jewish centres, the chaos of World War I marked a period of mass escapes, migration, and a total reorganisation of economic relations, particularly the loss of the Russian and German market. In 1921, only 2,834 Jews lived in Grajewo – 36.6% of its total population of 7,346. The Jewish community constituted a smaller percentage in the town’s demographics, but it continued to be an active, visible group exerting considerable influence on the local life. It owned two synagogues (at Rudzka Street and Powiatowa Street), a cemetery between Rudzka Street and Ślepe Jeziorko, a mikveh at Łazienna Street. The Jewish school network was thriving, both when it came to religious education (cheders) and secular facilities. One of the most influential forces on the local political scene was the Agudath (its branch was opened in 1921), uniting ca. 200 families – mostly Ger Hasidim, that is the followers of the tzaddik from Góra Kalwaria. The Zionist movement continued to grow in power, especially thanks to its youth wing. In 1939, Jews constituted 38.6% of Grajewo’s population, which amounted to 9,173 people.

Grajewo was seized by the Soviets soon after the outbreak of WWII (September 1939 until June 1941). The occupation brought an end to the previous economic model (nationalisation), but also allowed many Jews to find employment in the new bureaucratic and economic apparatus. Control over the town was then taken by Germans, who soon embarked on a campaign of murders, rapes, and acts of violence against Jews. The local ghetto was established in August 1941. Among its prisoners were also inhabitants of Augustów, Szczuczyn, and Rajgród. On 2 November 1942, the prisoners of the ghetto were transported to the camp in Bogusze and then gradually sent out – until January 1943 – to Nazi German concentration camps, where they perished in the Holocaust (a transport to Treblinka left the camp in December 1942; subsequent groups of people were deported to Auschwitz).