Some might say it would be silly to take a month-long cross country road trip with the New River Gorge Bridge as the main objective, but it’s an option I’m considering. I’ve always wanted to experience that place. The bridge and the gorge are famous to rafters, climbers and BASE jumpers, but I just think it’s a magnificent structure in a beautiful area of the country.
I know a couple who did this. They took their restored Cadillac convertible and traveled from Dallas to Southern California. Their rules were: No maps, No plans, and No interstates. They did it over the course of a few weeks, just wandering backroads in a generally western direction.
I did something roughly analogous to this once. I’ve mentioned on the SDMB that I sometimes deliver airplanes to new owners, and I decided one time to do it differently. About 5 years ago I picked up a Cessna in the PNW and wandered home to DFW without any reservations or detailed* plans. I had 5 days to get it back, so for each leg I just picked a small airport (mostly) at random and flew there. Sometimes I’d buy gas and fly a little further, or if it looked interesting I’d bum a ride into town. I had no hotel reservations and relied on rides from strangers to get to and from the airport. Surprisingly, it worked out fine and I never had any trouble finding rooms or a ride.
Answering the OP’s question, I’ve done quite a few of the things I wanted as a kid/teen. Operated a large crane, “driven” a large boat (48,000 tons, 650 ft), scuba dived (only once – I hated it), rafted the Grand Canyon, and flew a restored B-17 bomber.
There are a few odd ones left though.
-I want to see the “Blessing of the Fleet” in either Biloxi or Pass Christian
-I’d like to see the annual motorcycle gathering in Sturgis (not a motorcyclist, but I think it would be interesting to watch)
-Travel the Gulf Coast ICW (Intracoastal Waterway), spending a few months poking leisurely thru the harbors and towns**
*To the pilots; I did file a flight plan for each leg, once I’d decided where to head to next.
**Already bought the boat. Currently outfitting and testing for the trip (simulating it by spending nights on the local lake, measuring fuel mileage, how long I can run the generator per night, how long a tank of fresh water lasts, etc. I hope to do the trip in 2020).
I’ve traveled a fair bit, both across this country and internationally. But, I’ve never been east of Montreal. One day im hoping to get to the east coast for a visit, but also as a jumping off point for a road trip up and along full length of the North shore of Labrador. It’s not exactly well travelled but there are some amazing communities and it’s a remarkable route.
(Not exactly silly, but I’m not so sure it will ever get done !)
I want to train like an Olympian for any event and maybe try out for the Olympics. I also want to go on an awful date and escape through the bathroom window (like in the movies). Finally, I’d like to live and work in a huge city, simply because I feel that I’m cut out for city life and I’d like to get that ambition out of my system.
Edit: I’d also like to drive a fancy sports car and drive cross-country for a full week (not in the sports car, though.)
I would really rather see a live one.
I also want to swim in all five Great Lakes. I’ve done Superior and Michigan, so 40% of the way there.
I’d like to hike the Camino de Santiago but I’m running out of time…
(Hey, at least it’s not Pamplona…)
Edit: Oh, and climb Kilimanjaro, but ditto.
Well, depending. You could stay home and have a hamburger and a frankfurter, for practice. 
Once you’re there, if you’re not completely comfortable in the German language and want to follow this plan of adding “er” to the end of the town to order a sausage, then I suggest you not go to Donaueschingen or Niedereschach until at least the third day. And you might find yourself prejudiced against asking for a Rottenburger. 
I want to go around the world. By my definition, I would need to go to a place that is directly opposite of a place I had previously been. For example, I’ve been to Hong Kong and the point opposite to that is somewhere in north Argentina.
I want to go to Longyearbyen, Norway. The northernmost settlement with a population greater than 1000. There are daily flights from Oslo.
Easter Island…my parents subscribed to NatGeo and Smithsonian, so even as a kid, I devoured those magazines, there was a NatGeo spread on Easter Island that gave the whole history, good and bad, and had a pull-out insert map of the all the Moai…
What a diabolical thing to say…I like it…go on, we’re listening…
You might want to be careful with Berlin, too.
I’ve ridden on the Via Rail “Ocean” route, from Montreal to Halifax, four times. It’s awesome. The Canadian trains kill the Amtrak ones in terms of comfort and quality (the Amtrak people work very very hard and they do their best, but problems with the US rail industry ensure that Amtrak will perpetually be a third-stringer.) Via Rail is another story. Their sleepers are like miniature hotel rooms compared to the Amtrak compartments (the long-ass hallways that two people can’t pass each other in are kind of a pain in the ass, but there’s nothing to be done if you want the extra space in the compartment.) Everyone who can afford to should ride on that train, it’s spectacularly cool.
I want to see the annual bison round up in Custer State Park or Badlands National Park.
I want to see a night blast at Crazy Horse Monument.
I want to find one of the places that lets you rent earth moving equipment for an hour or two, and play in a great big sandbox.
I want to buy a new vehicle. Never could justify it in the past, used vehicles worked just fine for me. With my retirement from the big airplane company just around the corner, I am going to make it happen.
Also would like to drive a race car at Daytona. That will never happen. 
I want to see the Northern Lights. Not badly enough to spend possibly an extended trip in ice/snow or really cold weather to see them. If they were more predictable so I could see spend a weekend in Nome and be assured to see them I could do that.
or the Southern lights
Ditto for Rottweil…
My bucket list: I want to see attack ships on fire off the shoulder of Perseus.
They are notably shy and stealthy, but I managed to do this (in Benalla, VIC) a year ago. We waited quietly on a certain bridge that a certain platypus would cruise under most evenings around dusk. Got to see him / her four times.
As for kangaroos - yeah, they’re common as muck. Probably easier to find than white-tailed deer in the eastern US - and at least as common dead, by the side of the road.
Ooh, yeah, sorry – you’re lost, bub. See, look at this map of the Alnitak metro area, damn, can you help me unfold this, it’s huge, so, you see this truckstop here? That’s the Tannhäuser Gate, where you should’ve taken a left. Then you’d be just off the shoulder of Orion.
It could, if you were able to make a trip down there. I give you the Richard Petty Driving Experience.
I want to orbit the Earth. Unless some great disaster happens, with the way things are going it looks like there will be an intersection point between my net worth and the cost to take a short trip to LEO sometime in the next 20 years. I can hold out that long.