I am toying with the idea of exploring WDW in late evening, after our younger DD is asleep. DH and I can take turns each night to visit Disney Springs or another resort (we are staying at ASMov with not many late night options).
What would be your top 3 favorite places to go between 9 pm and midnight outside the parks?
I have very little experience with this, but when we were there last year my husband and I took turns walking the boardwalk at night - got some ice cream from Ample Hills, watched the Epcot fireworks from the bridge, walked around the lake looking at the lights. It was really nice.
Jellyrolls on the BW is a lot of fun; 21+, but does have a cover charge. Trader Sam’s at the Poly is a lot of fun as long as you are at the inside bar vs. the terrace (the terrace is nice enough, but nothing really special). And of course DS. Raglan Road is probably my favorite location (whiskey, Guinness, and music), but there are many other places for a late night drink and/or entertainment. If you’re looking for quiet, relaxing, and a touch elegant, the Enchanted Rose that opened where Mizner’s used to be at the GF; the photos look stunning.
We will sleep at home! 
Not surprisingly, these are some of the places I was considering!
I second Raglan Road. It’s my absolute favorite.
This was one of my favorite memories from last year. We also tried to watch YeeHaw Bob at POR (we were staying there) but were just too tired and went to bed.
The bar at POFQ-they have a good Cajun band that plays most nights.
Completely forgot about this one! I think they were closed and re-opened recently?
I found a blog post stating it reopened the beginning of October. There was a comment made that the music had changed to jazz.
There are lots of good options in Disney Springs. We liked Enzo’s Hideaway. The Edison is fun and has entertainment at night but it gets crowded and the service at tables in the bar area was spotty. We ended up going to the bar to get drinks which worked out just fine. The bartenders were great.
AbracadaBar on the boardwalk - haven’t been but it is on my list!
Thank you everyone for your input!
I think we would both enjoy a bar with live music, so Raglan Road, Scat Cats and piano bar on Boardwalk will be at the top of our list.