The development of digitalization is a crucial aspect of agricultural progress, and expediting the establishment of digital systems is a significant driving force behind high-quality agricultural advancements in the current era. Utilizing data from 16 cities within Shandong Province in China between 2014 and 2020, we created an assessment system to measure the degree of agricultural digitalization, utilized the entropy technique to assess the level of digitalization, scrutinized the general trends and time-dependent features of each city, and then utilized the obstacle degree model to pinpoint the primary hindrances to digitalization in agriculture. Lastly, the ESDA method was utilized to examine the differences in spatial distribution among regions and the spatial characteristics of agricultural digitalization at different stages and levels. Overall, the degree of agricultural digitalization can be categorized into three stages: deceleration and upswing (2014–2015), steady fluctuation (2016–2017), and high-level upswing (2018–2020). From the perspective of obstacles, the main hurdles to agricultural digitalization are e-commerce transaction volume and the total amount of telecommunication business. To accelerate the development of the entire agricultural industry chain, it is required to leverage the strengths of high-value areas and reinforce the coordination mechanism among various departments while hastening the construction of rural infrastructure in low-value areas. Additionally, it is necessary to improve inter-regional communication and cooperation to nurture different regional development models in line with local conditions.