I've had a number of small experiences that have helped shape the way I view life and my practice. These are mostly from talks and readings that were emotionally or spiritually moving for me. I cannot say I remember all of them...that's impermanence for you.
There is one time in which I was listening to a talk given by Ajahn Brahm of the Thai Forest tradition. Allow me summarize...
Ajahn Brahm told a story about a Samurai who would ask everyone he met the nature of the realms of heaven and hell, or if they even existed. People gave him a number of answers, which he was never happy with. He finally asked a monk, who told him, "You're too stupid to understand!" After a while of this harsh speech, the samurai was so angry and on he verge of killing the monk that he finally said, "Samurai, that's hell." The samurai understood the monk's words based on this experience of anger. He bowed to the monk with deep gratitude and tears in his eyes. The monk then said, "and that, samurai, is heaven."
This moved me to tears as well and it was a sort of renewed sense of understanding for me. It reminded me of the teaching of ehipassiko, "come and see", but also offered me comfort in devoting myself to the Dhamma. On a similar note, I've had my own direct experiences of insight from time to time. One of particular importance was during a meditation session at a tea shop near my school. This was the first time I had practiced in the presence of others, though I cannot say that influenced me all that much. After about 15 minutes of anapanasati, I had an experience I've never had before during my practice. My perception instantly expanded and I felt as though I became part of an enormous amount of space. I cannot say I understood what I was experiencing, as it is difficult to define it as either empty or full. It was just a strong expansion of peace.
Then again I could have just been going crazy, haha. In either case it was a wonderful experience that helped support my meditation practice and took away a certain amount of uncertainty I held before. At the same time I see it as a good tool to remind me that I should not hold on to and try to simulate such experiences, but rather to continue my efforts in the present moment.