More than 750 years ago Rakvere Castle was also named Wesenbergh.

During the tsarist period, the same street was called Peterburi and during first German occupation, it was named after Prince Heinrich. Since the beginning of Estonian independence, the street has a proud name of Tallinn. First wooden house at the current place of a brick building was built by Russian church priest Stepen Roždestvenski. By the end of 19th century there has been a bakery and pastry shop, spirit cellar and a shop in this building.

Later the building belonged to Mr. G. Kansbergh, who was the mayor of Rakvere for a brief time. In 1907 Mr. Kansberg built a two-story brick house – current Hotel Wesenbergh. Shops were on the ground floor and apartments on the second.

In the final years of The Estonian Republic in 1937 there was a police station in the building and a local perfect had an apartment on the second floor. In 1940 the house was nationalized, prison cells for those who got arrested were located in the court yard. 1941 the building was damaged during the bombing and stayed in ruins until the end of war. After the war it was renovated and in 1948 guesthouse Oktoober opened its doors.

1993 Restaurant Wesenbergh was opened. It seated 80 people.

1994 Hotel Wesenbergh was opened, which accommodated 28 people.

2001 The extension was built, that added room for 40 more people. Also the luxurious A. Pärt suite was completed.

2003 Villa Wesenbergh was built, that separately accommodates a company of 20 people.

2005 Kuur-Saal was opened, that is a great party venue for up to 120 people.

2013 The Wesenbergh restaurant and lobby were completely renovated

2018 All rooms were renovated.