A few favourite spots:
Stone Circle 
Kenmare Heritage Walking Tours with Anne-Marie Cleary
Maison Gourmet - French Cafe and Bakery
Cleo Gallery - unusual shopping and next door is Style on Shelbourne for a fun outfit
Kenmare Icecream - don't miss this!
Poff's - just off Henry Street for a lovely coffee or lunch break
Times Square delivers first class burgers etc.
Davitt's on Henry Street is known for its consistently good meals
Crowley's is the place for music - 9pm onwards or stop in for a pint
Weavers of Ireland for quality gifts
Alain & Christine's for a special bottle of wine and Christine has such unique cards
Norman McCloskey Art Gallery Kenmare photo courtesy Norman