I think it would be a fun little trip. Block Island is a totally different world when it's not filled with SUVs from the tri-state area.

There is a handful of good year round restaurants in Old Harbor. Flying is a cool option too, especially for a special occasion. It's a little pricey but the view can't be beat (http://blockislandsairline.com/index.php/block-island-flights/).

http://blockislandsairline.com/index.php/block-island-flights/