It's always hard to predict exactly when the best time of year to visit a town is, as it often depends on the travelers own preference. However, based off of the impressions of those who have been to Maidstone several times, it is often the case that visiting in the spring and summer is the best time of year to go. Visiting in the fall is also a good choice, but you won't be able to see as many of the festivals and activities if you visit later in the year. If you visit in the winter you will have to deal with the cold and often times unpredictable weather. If you come to Maidstone in the spring or summer you should pack with clothes that will keep you comfortable. If that includes shorts and t-shirts, that is fine. You should also bring a pair of pants and a light jacket for night though. Also, if you want to go out to nice restaurants or clubs at night, bring some nice clothes as well. If you visit in the fall or winter, you should definitely bring warm clothes, as it can get quite cold, especially at night.