Hysteroscopy is an endoscopic diagnostic and therapeutic method traditionally performed under general anesthesia but increasingly under local anesthesia. Today, it is considered the gold standard in gynecology. This minimally invasive procedure allows for a detailed assessment of the uterine cavity’s interior and the removal of abnormal changes within it and is applicable to patients of all ages. Background/Objectives: The purpose of the present study was to evaluate pain during hysteroscopy under local anesthesia at different stages of the procedure, identifying which stage is the most painful (GUBBINI Mini Hystero-Resectoscope; Tontarra Medizintechnik, Tuttlingen, Germany). Methods: The study included patients between the ages of 21 and 80 years. They were divided into two groups: the diagnostic hysteroscopy (HD) and the operative hysteroscopy (HO) groups. Pain measurements on the VAS scale were taken at each stage of the hysteroscopic procedure. After each stage, the operator asked the patient to indicate the maximum perceived pain value: after pericervical anesthesia was administered (VAS1), during the installation of equipment (between the removal of the speculum and the insertion of the hysteroscope into the vagina) (VAS2), after insertion of the hysteroscope and visualization of the external orifice of the cervical canal (VAS3), after passage of the hysteroscope through the cervical canal (VAS4), and after completion of the procedure in the uterine cavity (VAS5). The duration of each stage of the procedure was measured with a stopwatch: administration of pericervical anesthesia (T1), time between the removal of the speculum and the insertion of the hysteroscope into the vagina (T2), insertion of the hysteroscope into the vagina until the outer orifice of the cervical canal became visible (T3), passage of the hysteroscope through the cervical canal (T4), and the hysteroscopy procedure itself (T5). Results: The highest pain rating was for the canal passage stage (VAS4: 2.47 ± 2.48 points), followed by the procedure itself (VAS5: 2.12 ± 2.33 points). Anesthesia was also reported as quite painful, while the lowest pain was noted during the assembly stage. Overall pain scores for the entire procedure (VASmax) ranged from 3.5 ± 2.37. Conclusion: In conclusion, we found that the passage through the cervical canal was the most painful moment. Overall, hysteroscopy under pericervical anesthesia was not associated with significant pain. Special attention should be given to postmenopausal patients, as they experience more pain during the passage of the hysteroscope through the cervical canal. This group may benefit from additional pain management strategies during the procedure.