While Bourton-on-the-Water is not, in itself, a beehive of events, there are numerous events and festivals taking place year-round in the general region of the Cotswolds, for example, the Frampton County Fair in September in Frampton-on-Severn. The 2nd Annual Gypsy Horse Fair takes place in October in Stow-on-the-Wold, a mere four miles from Bourton-on-the-Water. After checking out the Horse Fair, check out Cheltenham Racing at the Paddy Power Open in November (if you're there that long).

Another event in October is Day Out with Thomas at the Gloucestershire Warwickshire Railway, as children's story character Thomas the train and his friends celebrate two days of fun with their fans.

Imagine strolling Bourton-on-the-Water's 15th and 16th-century streets and playing Santa on the first of December's Victorian Evening late night Christmas Shopping event. For cheeseheads, the Great British Cheese Festival takes place in Cheltenham in late September, with tastings (extra-sharp cheddar, please), workshops, and a cheese-toss.

Farmer's Markets take place throughout the year in Stroud, Stow-on-the-Wold, and several other locations near Bourton-on-the-Water. Here's a handy Farmer's Market schedule. Guided walks also take place throughout the year, with Bourton-on-the-Water often as a starting point, destination, or visiting point.