So I made some changes to Doc's route just as an example of what we would have to do to make this work out.
This is on an 8:00PM to 2:00AM time schedule making a six hour full crawl, with two 3-hour mini-routes.Full routePre-Dick's short routePost-Dick's short route
(Note: I removed the Elysian for this example because 8 stops is one too many, but any other bar could be removed instead if that's more worthwhile)
If there's a big turnout, half of the people attending would be going backwards (Starting at Six Arms) and meeting up at Dick's in the center, so half-route people could choose a pass on either side, early or late.
That would basically make the schedule:
(X:XX XX - Group A / Group B )
8:00 PM - The Chapel / Six Arms
8:50 PM - The Stumbling Monk / Linda's
9:40 PM - Cafe Metropolitan / Barca
10:30 PM - Dick's --Midpoint. People leave/arrive.
11:20 PM - Barca / Cafe Metropolitan
12:10 AM - Linda's / The Stumbling Monk
1:00 AM - Six Arms / The Chapel
1:50 AM - Crawl ends/Last Call
Throw in some extra minutes for travel time because they aren't equal distances and it sounds like it could work