The Rock Cafe features a piano bar indoors every night of the week, with a speaker set up for the diners outdoors. the music is generally geared towrards the middle aged sailing & cruising set, but the quality of the performers I heard there was terrific.
Maybe Elton John isn't your thing, but the 2 young UK pianists would've wowed him too with their outstanding keyboard talents. They also took requests, everything from old romantic standards to Led Zeppelin, giving each a unique spin and a fine piano flourish.
Dress Code: This is NOT the Hard Rock Cafe, it's named for the rocks at the Baths. The atmosphere is suitable for anything from nice shorts & shirts with decent sandals to cocktail dresses & suits.
Remember, this isn't road Town or Charlotte Amalie, so it cannot support a wild night life. That being said, I think they do a really good job of entertaining their guests every week on VG. You just have to ask where to go. The bartender at the Bath & Turtle, your dive master at Dive BVI, the receptionist at your hotel...just ask them all, and you'll find out.
E.g., the Bath & Turtle had a live rock band on Wednesday night, Chez Bamboo had live jazz another night, there was a reggae band playing 2 nights running at the Christmas street fair by the Marina. You get the idea. If entertainment matters to you but you are determined to stay on VG, then you should either count on staying near Spanish Town, or stay at the large resort Bitter End Yacht Club, where there's all sorts of entertainment available regularly.
There is no nightlife in Virgin Gorda. OK, so September is the slowest month, but I can't imagine it's any different in high season. I'm not complaining, we weren't looking to dance until 2 am. We did listen to a guitar player at Little Dix Bay's bar after having dinner there and it was very nice, but there is nothing to do after dark.
Dress Code: Almost everywhere shorts and a nice polo shirt are more than fine. I wore pants and a long sleeve dress shirt at Little Dix Bay to feel dressy. Leave your blazer and ties at home.