We have taken several extended family trips and one restaurant my mom always used to want to go to was Rose and Crown. She swears that it's a tradition but for the life of me, I don't remember going there as a kid but maybe I just wasn't paying attention?
However, about 10-12 years ago, I can't remember for sure which trip it was, DW and I tried Raglan Road for the first time. That one has become a tradition and we go once every trip. We always start our trips with a Disney Springs day so we can go to the Christmas shop, find an ornament and order personalization, and do a little start of trip souvenir shopping for things we know we will want (usually a picture frame).
I tend to get something different almost every time, not because I haven't enjoyed what I order but because so many things sound good. Over the years I have had the bangers and mash, shepherds pie, the steak, pork shoulder, chicken sandwich, and fish and chips. However, DW and I both love scallops and we get the scallop forest appetizer every time and always love it. DW has had a few different things and enjoyed them all but given her fondness for scallops and gnocchi, once she tried the gnocchi she has never gotten anything different. She is very picky about gnocchi too and has loved this every single time.
The music and dancers are great too and while the musicians stay on stage in our experience (maybe we've just never seen them wander) the dancers will sometimes make the rounds to some of the side areas of the restaurant. We got a great picture of DD with them around her high chair.
Rose and Crown, on the other hand, has had a few menu changes over the years and things that we had tried in the past aren't there anymore, and it feels to us (just the opinion of one family, bear in mind) that it just isn't as good as it used to be and we haven't gone back in probably 6-7 years now.