Reflecting German baroque cabinets of the 17th and 18th centuries and the expressionist style of the 1920s, the wooden Rakvere door has a pointed, raised rectangle in the center.

[1] The earliest signs of a human settlement, dating back to the 3rd, 4th, and 5th centuries AD, have been found on Rakvere's theatre hill (Teatrimägi).

The Battle of Wesenberg, with the Danish and Teutonic knights and local militia on one side and the forces of Novgorod and Pskov on the other, occurred near Rakvere on 18 February 1268.

[1] After the king sold Danish Estonia to the Livonian Order in 1346, a large stone castle was built on top of the stronghold on Vallimägi.

Yet, in 1558, during the first year of the Livonian War, Muscovite troops captured Rakvere, and, in 1574, Sweden heavily damaged the town after the disastrous Siege of Wesenberg.

During the period of independence from 1918 to 1940, Estonia completed its first railway, and Rakvere was at the heart of the crucial Tallinn-Rakvere-Narva-St. Petersburg trade route.

Rakvere Theatre has given Estonia many renowned actors, including Volli Käro, Üllar Saaremäe, Indrek Saar, Ülle Lichtfeldt, and Aarne Üksküla.

The Tallinn-Narva railway passes the city, and passenger trains between Tallinn and Narva, operated by Elron, stop at Rakvere several times a day.

Daily busses connect Rakvere to Tallinn and Narva, too, as well as to many small towns throughout Lääne-Virumaa, including Tapa and Kunda.

There are 19 districts, or neighborhoods, in Rakvere: Kondivalu, Kukeküla, Kurikaküla, Lennuvälja, Lepiku, Lilleküla, Linnuriik, Moonaküla, Mõisavälja, Paemurru, Palermo, Roodevälja, Seminari, Südalinn, Taaravainu, Tammiku, Vallimäe, Vanalinn, and Õpetaja Heinamaa.

Throughout the ages, Rakvere Castle has belonged to Danish kings, knight-monks of the Livonian Order, and the Swedish and Polish states.

The church's interior displays fine craftsmanship, including a Baroque pulpit from 1690 made by Christian Ackermann[20] and the altar wall from 1730 by Johann Valentin Rabe.

In 2020, as part of the EV100 "Good Public Space" program, approximately 700 meters of Pikk Street were reconstructed, making it a pedestrian-friendly, historical thoroughfare reminiscent of the 19th and early 20th centuries.

The so-called Carrot Stairs (Estonian: Porganditrepp) with wider steps at the top and little ones at the bottom lead up to Vallimägi and Rakvere Castle ,[22][23] In 2004, Rakvere's central, or town, square got a new, modern look with architects' Otto Kadarik, Mihkel Tüür, and Villem Tomiste's five yellow domes (or umbrellas or chanterelle mushrooms or medieval turret tops) hanging from white semi-arches on cobbled hills.

In 2010, the sculpture A Young Man on Bicycle Listening to Music was dedicated to Estonian composer Arvo Pärt, an honorary resident of Rakvere, in honor of his 75th birthday[24] The sculptors are Aivar Simson and Paul Mänd.

[25] (Across the street from Freedom School the Municipality of Rakvere is converting St. Paul's Church, also designed by Kotli, into a multipurpose music center in honor of Pärt.