Szczytno, which is located on the Olsztyn – Ełk line, and used to be a railroad junction until Polish Railways closed minor connections stemming from the town towards Czerwonka and Wielbark.

The first mention of the fort, eponymously named Ortulfsburg, was a document from September 1360, after Ortolf invited Polish colonists from nearby Masovia, among whom the settlement became known as Szczytno.

In 1454 King Casimir IV Jagiellon incorporated the town and region to the Kingdom of Poland upon the request of the anti-Teutonic Prussian Confederation.

[3] With its inclusion in the Ducal Prussia in 1525, which remained under Polish suzerainty, it lost its importance as a border fortress and began to decline.

Prussian King Frederick William III and Queen Louise arrived in the town on 23 November 1806 while fleeing French troops during the Fourth Coalition.

[8] The town was briefly the seat of the Prussian government, and Frederick William released his Ortelsburger Publicandum — a series of constitutional, administrative, social and economic reforms — there on 1 December 1806.

[7][11] Ortelsburg was almost completely destroyed at the beginning of World War I by troops of the Russian Empire, 160 houses and 321 commercial buildings burned down between 27 and 30 August 1914.

[12][14] The initial plans for the reconstruction of the town were based on Bruno Möhring's work but carried out by several local architects.

[12] The East Prussian plebiscite of 11 July 1920, which was held according to the Versailles treaty under the supervision of Allied troops, resulted in 5,336 votes for Germany and 15 for Poland.

[18][19] During the interwar period, Polish-speaking residents of the region organized Samopomoc Mazurska ("Masurian Self-Help"), an organisation for the protection of Poles in southern East Prussia.

The first group of Poles expelled from former Eastern Poland, which was annexed by the Soviet Union, arrived to Szczytno in June 1945 from Volhynia.

[7] The nearby Szczytno-Szymany International Airport, as well as Stare Kiejkuty, a military intelligence training base, came under scrutiny in late 2005 as one of the suspected "black sites" (secret prisons or transfer stations) used in the CIA's program of so-called extraordinary rendition of accused terrorists.

The existence of the nearby training base and the record of CIA-registered affiliated aircraft having landing at Szczytno-Szymany have been unequivocally confirmed, but the Polish government has repeatedly denied any involvement of these facilities in extraordinary renditions.

[27] Among the historic sights of Szczytno are the ruins of the castle, the pre-war town hall, which houses the municipal and county authorities, as well as the Masurian Museum (Muzeum Mazurskie), dedicated to the history, ethnology and culture of Masuria and Szczytno, a Baroque Evangelical church, the pre-war Polish House (Dom Polski), which was the center of social and cultural life of the local Polish community during the times of Germanisation and the well-preserved old wooden Masurian House (Chata Mazurska).