Did it in 2016 during my build-up to IM Canada, which was a mistake for reasons not really pertinent to your post. Although obviously extremely difficult, it's a fantastic event – very well run, great scenery, and great roads. How you prepare depends somewhat on your goal for the event. The common denominator is going to be doing as much mileage as you reasonably can do, with a consistent weekly long ride in 4-6 hr range (the event will take you longer, but a 7-8 hr ride is overkill, except maybe once or twice).

If you're looking to stay with a group or ride the climbs/KOMs hard, then you need to be able to do repeated 5-15 min efforts at FTP to VO2 max intensities and do them in the course of a 7 to 9 hr ride. For basically the entire course, you're either hammering up a climb at some insane grade, or descending the mountain you just climbed. So this means both dedicated interval sessions at durations and intensities that match what you plan to do on the climbs, and then later incorporating these sessions into your long rides. I wouldn't worry too much about not being able to simulate the terrain with your outdoor riding. Unless you live in Garrett County, MD, you're going to have a hard time matching the terrain anyway. Most of the climbs aren't very long, but they are all very steep and they come at you relentlessly. I don't think there are too many places like it.

On gearing, your 34x28 is adequate but maybe not ideal. I got by with a 36x28, but if I did it again I would want a 30 or 32. My friend who is super-strong (50-54 National Road Race Champ) did it with a 34x32, I think.

Good luck!

The event is happening in 2018, so you can rest easy there.

As you've got a Tacx Neo you can reasonably approximate the grades, so I would subscribe to Cyclops Virtual Trainer for the winter and ride the actual DD route segments. It is a pretty good simulation of the actual ride to video of the actual route, although the dreary, gray day the video was taken doesn't nearly do justice to the actual beauty of the region. The CVT simulation caps the pitches at something like 12-13% so there are definitely times where the road is steeper than the CVT trainer simulation, but you'll certainly get to know the course and a good sense of what it's like. I know there's a guy from Texas who has ridden 3 years in a row now and who trains exclusively to these videos and every year he comments that the actual ride is harder but that training to the CVT simulation is invaluable. I don't know; to me the trainer is insufferable however you go about it.

http://garrettcountygranfondo.org/trainer_vids.htm


As far as gearing goes, if your rear derailleur takes a 32 then put it on. In all the years of SavageMan and Garrett County Gran Fondo never have I heard someone express regret of having put on a crazy granny climbing gear, while the lament of having failed to do so is a common refrain.


The DD is a monster ride. A true epic. Enjoy it! Here's a nice writeup of someone who did it this past year

This is always my favorite event of the year. I don't think it's absolutely necessary to train on hills to be prepared to tackle this ride. If you can get in some long rides with hard intervals it will help simulate the day.

I rode this year with a 52/36 with a 28 in the back and it was fine. If you can fit a 32T, it might be nice to have a that bail out gear and you can keep spinning up the hills for longer.

For this ride, I'm either in my 34x28 or in my 50x11. If I had a 30 or 32 in back, I'd put that on (remember to think about whether your RD can handle it).

If you're in a flat area, you probably have wind. Practice riding while standing into strong headwinds. Your triceps and shoulders will thank you.

And look forward to it! It's a great ride.