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The starting point for hiking the tallest mountain in Colorado, Mt. Elbert, is ensuring the dad won’t die. Ideally he is not too old and not in might-need-an-airlift kinda shape. Luckily mine found a second wind in life and has been working out constantly. Once you are confident the dad won’t die, it is wise to consider one’s own health. Ideally you can walk/run several miles, have hiked before, and live near mountains. If you aren't, just send it. With enough stupidity and ability to endure suck much can be achieved.
A couple of months before you plan on going start baiting the trap. Slip in subtle phrases like “I’ve wanted my whole life to hike with you” or “you’re in such good shape, I’m sure it would be easy to hike a mountain”. Get the dads’ confidence up. Lure them in slowly and softly.
For those with red-blooded dads from the flatter states, aka the Midwest, I highly suggest not playing the nature card. Nature is a foreign and unappealing concept to them.
Once the prey has been caught and the trip has been set it is now your part. Coordinate and plan everything. Ideally look at Breckenridge or Leadville due to their proximity to Mt. Elbert. Write out a list of gear needed. Get the snacks. Bring lots of water and hiking poles. Always bring hiking poles. Find and map the route. Plan the drive. Do it all.
It is key to act the adult on this occasion. You must be the leader and stoic personality. The hike will hurt. Both of you will not be prepared nor acclimatized. Ignore this and all legitimate, helpful advice. This is basically a soft-core suicide mission. Prepare the night before with breakfast of some kind and get everything ready. Wake up early, give the hike plenty of time.
Once you both have set feet onto the hiking path take a moment to celebrate yourself. You’ve done more than most on making this happen. Let the hike build slow and get the legs prepared. Ignore the healthy, fit people around you, let your inner Midwesterner tell you how much to push. Once the hike really starts hurting, do not engage the dad complaints like “I just don’t know why you like this”, “Im scared of heights, “Beaches are way better than mountains”. Ignore ignore ignore. Just keep pushing.
Upon summiting take three pictures, one of the scenery, one selfie, and one with your dad, then prepare to leave. Likeliest the dad will not want to stay at the summit and will want to leave. Again, they do not understand nature. This is okay, mission has been achieved. Leave the mountain as fast as possible. At this point both of you are probably in a lot of pain and grumpy. It may be wise for the younger and/or fitter person to jump ahead of the Dad and give each other space.
Once at the car, accept the burden of driving and speed your way back to the hotel. Say good job, quick, and take a nap. The dream of hiking with your dad has been achieved. Congratulations.