Check out the Wolfeboro Chamber of Commerce website - www.wolfeborochamber.com - for scheduled fairs and special events throughout the spring, summer, and fall seasons.
The Great Waters Music Festival - www.greatwaters.org - hosts a schedule of weekly performances for all ages from May through August.
And of course, don't forget to join the Friends of the Wolfeboro Community Bandstand at Cate Park for music (and always dancing!) under the stars every Saturday evening from 7-9PM. The town docks will be full of boats and the ice cream is plentiful!