The historical Dobrzyń Land covers an area marked by the Vistula, Drwęca and Skrwa rivers. The Slavic ancestors, who inhabited this region as early as in the 6th century, valued it for favourable climate, fertile soil, abundant wildlife, forests with plenty of animals to hunt, and lakes and rivers  providing them with fish and drinking water. Numerous islands and penninsulas on local lakes proved perfect for settling, offering natural protection from unwelcome visitors. Today, archeologists continue to uncover traces of Mesolithic hunters (8000-4400 BC) and first Middle Neolithic farmers (3500-2500 BC) in this area. In the second and first millenia BC the land was inhabited by tribes with rich spiritual life, the creators of cultures recognised by pottery shapes (e.g. funnel-shaped cups and globular amphorae) and pottery ornaments (e.g. linear  pottery, corded-ware pottery).

Nowogród near Golub-Dobrzyń, situated on a conical steep hill at Lake Grodno, may serve as a good example of how a convenient location attracted  a succession of peoples. Three or two thousand years ago this hill was a peninsula or an island. Later,  human settlements were turned into a farmland, which today is covered with shards of pottery typical of the Lusatian culture (ca. 1500 BC) and the Iron Age.  That was when the Slavs arrived. Their defensive  settlement, representative of the early Middle Ages, survived until the 13th century, when modern towns and villages, distinguished by brick buildings and fortifications, were founded under the Chełmno Law (Kulm Law) and  the Polish Law. 

Similar settlements, surrounded by palisades and earthen ramparts, emerged between the 8th and 13th cc. on both sides of the Drwęca river, a natural border between the Dobrzyń Land and the Chełmno Land, the neighbouring districts of the Duchy of Mazovia. Their construction ensured protection from the attacks of Prussians, Lithuanians, and Ruthenians. Even today it is obvious that those settlements communicated through visual signals to warn one another about approaching enemies, relying on smoke during the day and on fire at night. In the Dobrzyń Land archeologists found traces of 30 early-medieval settlements, which provide evidence that this part of Mazovia was already densely populated and well-developed at the dawning of of the Polish state. From the 11th c. the Dobrzyń Province was owned by the Mazovian line of the Piast dynasty residing in Płock. At that time Dobrzyń was a defensive town and a seat of castellany. In the 12th and 13th cc. the heathen Prussians, still  resisting Christianity, organized rapacious expeditions to Mazovia. This prompted Duke Conrad of Mazovia to use the  Prussian Order of the Knights of Christ to support the Christian mission already undertaken by the Cistercians from Łekno in Wielkopolska (Greater Poland). Settled in Dobrzyń in 1228, the members of the order were commonly referred to as Dobrzyń brothers or 'dobrzyńcy'.

They did not develop the expected activity but joined forces with Teutonic Knights (the Order of Brothers of the German House of Saint Mary in Jerusalem), whom Conrad of Mazovia invited to Poland at the same time. This inevitably led to trouble because the Teutonic Knights asserted the right to the Dobrzyń Land as a dowry obtained earlier from Conrad of Mazovia. Conflicts instigated by Teutonic Knights demanding rights for several regions in Poland made  the Dobrzyń Land a bulwark against the Teutonic threat. All Polish kings from Władysław Jagiełło (Ladislas Jagiello) to Stanisław August Poniatowski placed the crest of the Dobrzyń Land on great seals of the Polish Crown among the crests of the most important provinces of Poland. 
The crest is also found on the tombs of Władysław Jagiełło and Kazimierz Jagiellończyk (Casimir Jagiellon) in the Wawel cathedral. For 300 years of the First Polish Republic the Dobrzyń Land was incorporated  into the Inowrocław Voievodship. Sejmiks (regional assemblies) of  the Brześć and Inwrocław voivodeships in Kuyavia were held in Radziejów and did not address the matters  connected with the region stretching on the other side of the Vistula River. 
In 1352, after the death of the last Duke of the Dobrzyń Land, the castellan of the Dobrzyń Land became the chief government official in the region. He performed the duties of a voivode while the Dobrzyń Land constituted an independent administrative unit almost equal in rank to a voivodeship. The starost's office and the court were seated in the old Teutonic castle in Bobrowniki and sejmiks were held in Lipno.The Second Treaty of Toruń (1466) brought harmony and stability which continued for the rest of the 15th and the entire 16th century. The towns founded in the Middle Ages (Dobrzyń – before 1239, Górzno – 1327, Rypin – 1345, Bobrowniki – 1403, Skępe – 1445)  developed into trade centres while landed properties belonging to knights and monasteries strengthened economically. Forests offered favourable conditions for the development of hunting, bee-keeping and many branches of forest industry including tar-burning and charcoal and birch-tar production. The Vistula and the Drwęca were used for floating wood and transporting manufactured goods and agricultural products to Toruń and Gdańsk. The treasure of the Piwo family (discovered in the old settlement in Skrwilno) – mainly silverware and jewellery –  may serve as a good indicator of  the high social and economic status that knights enjoyed at that time.
 Years 1601-1660s were marked by Swedish invasions, fires of castles, towns and villages, and deadly epidemics. 
Then the following period of economic growth and cultural revival was brought to a halt by the Great Northern War. Between 1700-1721 the Dobrzyń Land was systematically devastated by the Swedish, Saxon, Russian, and Polish troops sweeping through this territory. 
The inhabitants of this land participated in all Polish uprisings. In 1920, during the invasion of the Russian Bolsheviks they stood up to defend Poland's independence, achieved barely a year before. During the Second World War (1939-1945) the Germans, who incorporated the Dobrzyń Land into the Third Reich, deprived the Polish people of their rights, took cruel repressive measures and launched a displacement policy. 
Many intellectuals, teachers, social activists, and clergymen who were recognized and denounced to new authorities by  German inhabitants, were brutally tortured and murdered during the first months of the Nazi assault. The Nazis continued the extermination of the Polish people until the end of their occupation. The Museum of the Dobrzyń Land in Rypin, housed in a former Gestapo headquarters, presents a fearsome exhibition of German crimes. However, many members of  patriotic organizations (the largest of which was the Home Army) put up determined resistance to the Nazi rule. 
Statues, obelisks and plaques commemorating national heroes can be seen in all major places in the Dobrzyń Land. On cemeteries you can find graves of the participants of national uprisings including the Kościuszko Uprising 1794 (in Świedziebnia,  Trutowo, Wielgie), the November Uprising 1830-1831 (in Obory, Skępe, Górzno), and the January Uprising 1863-1864 (in Radziki Duże, Rypin, Chrostkowo, Szczutowo, Tłuchowo, Wąpielsk, Trąbin, Ligowo, Skrwilno, Skępe, Sadłowo). Those who defended Poland from the Bolshevik invasion in 1920 are commemorated in  Skępe, Dulsk, and Ostrowite. A cross near the dam on the Vistula (joining Kuyavia and Dobrzyń), commemorates the martyrdom of Jerzy Popiełuszko, the chaplain of the Solidarity trade union, and symbolizes Polish struggle with the communist regime. 
Wayside brick or stone shrines and wooden or metal crosses can be found in almost every village. Dates as well as religious and patriotic invocations engraved in them confirm their documentary value. Perceived as symbols of the Polish spirit, they were ruthlessly destroyed by the Germans in the autumn of 1939. However, the local people, for religious as much as for patriotic reasons, hid the remains of the shrines and crosses. When the Nazi occupation was over the Polish symbols of faith were reconstructed meticulously.The Dobrzyń Land is the homeland of two contemporary Poles who made important  contributions to Poland and the world: Lech Wałęsa (born 23 September 1943 in Popowo in the Lipno District), a heroic leader of the Solidarity trade union,  major political figure, President of the Third Polish Republic (1990-1995), Nobel Peace Prize Winner (1983), and Leszek Balcerowicz (born 19 January 1947 in Lipno), an outstanding economist, major political figure, finance minister in Tadeusz Mazowiecki government, who executed his plan of transforming the socialist planned economy into the social market economy (a deed of unprecedented historic value). He was awarded an honorary degree by 11 universities in eight countries.