I do like the idea of ferry rides as a group. And anything up north in the summer sounds nice too. Has a fest done the Roanoke yet? I know that requires a very short overnight there, but I've been wanting to cover it.
Milwaukee and Detroit are probably good fests too as there's always something to ride in Chicago or a quick roundtrip on an Illinois train. I was just thinking the Cincinnati streetcar is a nice run, but I'm not sure how that could work with such horrible calling times and 3 day a week Cardinal service.
Chris, I've done the Lake Champlain Ferry circle tour in both directions several times... mostly involving the Adirondack at the seasonal Port Kent, NY station and the Vermonter at Essex Junction, and once involving a now-defunct Thruway bus between Burlington and Rutland hooking up with the Ethan Allen Express. Certainly I would not mind doing this again with a group. It is a scenic trip in the Adirondack and Green Mountains as well as the boat ride across the lake. However in thinking about what might be within a couple of years, the Ethan Allen Express is supposed to be extended to Burlington, whose Union Station is just steps from the ferry dock. Waiting to ride an extended Ethan Allen would provide us with even more new trackage (in addition to what one would get if they have not been on the Adirondack or existing Ethan Allen) and it would eliminate the need for an hour bus ride or a hired car between Burlington and Essex Junction to access the Vermonter.
I recommend this be done in the clockwise direction for now, as the walk in Port Kent is downhill and because the southbound Adirondack can be delayed at the border. The way Penny and I did it, to avoid an early morning departure on the Adirondack from New York, an extra night in Albany was added, going up the afternoon/evening before on an Empire Service train.
What Penny mentions about hotels in downtown Burlington is true -- they are quite pricey. They are pricey in July and maybe a little less so when we went in June. With more people it might be worthwhile to share Uber/Lyft and go out to where the bulk of the hotels are along Williston Road (US 2) in South Burlington. For those dedicated to the Hilton chain there is a Doubletree where that road crosses I-89. It's a busy commercial area.
Next, to deal with Roanoke. I am surprised that many in our circles have not yet ridden this Lynchburg-Roanoke segment; I went and did it in its infancy on a cold November weekend. It is best done on a weekend, as the weekday version of the train departs RNK a bit too early in the morning to be comfortable. I would not at all mind doing this again, either on a Friday out and Saturday back, or a Saturday out and Sunday back. One would not see much on the trip towards Roanoke given it's at night, but the views are better in the morning when heading towards the Northeast. I suppose this could be a trip based on Washington, DC or we could meet aboard the train at various stops. Doing this would be a self-sufficient trip, meaning there is not really much else to pair it with (unless we were to wait for the Silver Line extension to Ashburn, VA).
To Cincinnati. Yes they do have a nice streetcar ride, with the entire route shaped like a Figure-8. It is definitely worthy of a visit. And now here comes the H word. However, getting there is near impossible. It is correct that the thrice-weekly nature of the Cardinal, plus its poor calling times, work against a group visit like we would want to do. Before the demise of the Hoosier State, which along with the Cardinal provided not only a daily rail service between Chicago and Indianapolis but also a 2-hour Thruway bus connecting between Indy and Cincy, there was a viable possibility if folks did not mind the bus ride. When I went to Cincinnati in 2017, as long as I had to arrive by bus, I attacked it from the north, taking a Thruway connection from the Capitol Limited at Toledo. And we all remember that this side trip to Cincinnati and the severe delay incurred by the Cardinal caused me to miss the Kansas City portion of the MTRF trip that year.
Addressing Milwaukee and Detroit.... Milwaukee works any day of the week as there are multiple Hiawatha trains. Chicago-Detroit has 3 Wolverine frequencies, but only the midday one really works in order to have decent calling times at both ends. Detroit's streetcar is worth it, and it is convenient as it passes the Amtrak station. In discussing this with Steve, it may be better and more fun to wait for Amtrak to roll out its new rail cars on the Midwest lines.
Coming back to Steve's mention of the ferry between Long Island and Connecticut... Penny and I did this too several years ago. Counter-clockwise is better here. The Port Jefferson LIRR station is roughly 1 to 1-1/2 miles from the ferry, and for those who would walk it, downhill is obviously better than the alternative. A group could also do the Uber/Lyft route. On the Bridgeport end of the ferry, the train station is right there, and there are more alternatives there, either MNRR or Amtrak, to get one back to New York City, or wherever else they are headed. Another possibility that can be done anytime.
Steve also mentions a round trip to Montauk on the LIRR. This is a standalone full day round trip. There are not many options throughout the day that would allow for such a round trip in full daylight, and one also should be prepared to skip lunch/bring snacks. The trips are quite long and they likely will drag on past lunchtime but get us back to Manhattan around dinnertime. Nothing to eat at the Montauk station. Basically we would depart NYP around 10:30 AM and be back before 6:30 PM. Eight hours with about 1/2 hour layover in Montauk.
Doing the Port Jefferson-Bridgeport trip and the Montauk trip together would mean two full days, and a hotel stay in the NYC area in between if not before and after as well. July can be pricey... very much unlike previous stays in January. I am not adverse to such a journey but these are things to keep in mind. An open mind to stay outside the city in NJ or Connecticut or northern suburbs might be helpful.
Final thought: July doesn't have to be anything big. Last year when we did Toronto, it was 4 days involving Canada, plus we added two more in NY State to keep the calling times decent. It appears that I've established precedent to do 3 fests a year, so September is still ahead of us and that being in a more comfortable time of year we can do something in the South like Texas. What is planned for that trip involves 10 days starting & ending in Chicago (potentially with visits to El Paso, Fort Worth, Oklahoma City, and Little Rock), plus several more for those living on the east coast.