I am soon going to start on a journey across the US's longest road, Route 20, starting in Boston, and ending in Newport, OR. What interesting and cool stops would you recommend me making along Route 20?

Give me some answers I won't usually hear, as I am already going to places such as Yellowstone.

Additionally I plan on taking Route 40 or Route 50 (dubbed the "Loneliest Road") back home. Which would you recommend?

>>2806189
I don't think rt 40 goes anywhere that scenic - there's a nice brewery that sells pizzas and maple syrup and honey off of it somewhere in Western Maryland I wanna say near Cumberland that I've been to a few times.

Rt 50 is ok - stop at farmer's daughter butcher shop if you can - try to be there 11-3 for lunch
I recommend the city ham for meats - the pates are also nice.
It's a "real" butcher shop i.e. they sell cuts they chop up in house.

What you WANT imho is rt 48/55 to go westbound
From boston you would have to get over to 81 south - I recommend cutting through Eagles Mere or Del Water Gap
then you get on 48 west (also called 55) in the direction of Wardensville - and then from there it opens up into multi lane divided highway through the mountains - nobody will be on it - you have it to yourself - and sadly its not multilane the whole way - just till davis wv then buckhannon westward - davis has access to blackwater falls, dolly sods (drive up fr 75 (seasonally- this won't work in winter) - park where it says bear rocks - there's actually signs now I think of where to go - you walk on the edge to easy views - wear pants - it will be cold and there's heath bushes that hurt

there's also an overlook right off 48 just past davis before parsons on the right (westbound) that's nice for a photo - buckhannon has audra state park (trail along a river and swimming) then it goes west to charleston and then to lexington ky where you have the red river gorge 45 min away and then I don't know where it goes but you wanna route yourself through the mountains cuz that's the pretty bits - I haven't been west of there so can't help.

As for NY state I recommend picking out some gorges/state parks there's lots of them with views waterfalls - watkins glen, letchworth and rochester ny itself has waterfalls in it - tho its kinda a sketchy place - but don't miss upper falls - just realize there's a tiny parking lot next to the brewery which is the actual public parking

>>2806187 (OP)
That's a great cross-section of the country. I think you should take little detours to see Lake Ontario and part of the Michigan side of Lake Michigan.

The Midwestern plains are deathly boring on the interstate, but on the US highway you can get into the groove of hopping from town to town over the course of a day's driving. Yeah, it gets desolate in Nebraska and Wyoming, but that's part of the continental experience.

>>2806202
>watkins glen
Would recommend this state park. I hear letchworth is bigger, but watkins glen was pretty dope imo and not that long of a walk (depends on which side you start on) Also in Ithca there's a fairly big waterfall just off one of the streets that's worth dropping by. Takes all of like 5 minutes and is on the way to the east side of watkins glen.
>>2806187 (OP)
Can't speak to US-20 but in Nebraska I went through (most of) NE-2 which was a pretty nice drive with some decent views. I went form Dunning to Alliance then cut north to US-20. Just be aware there's not a lot of gas stations out there, i saw probably 3 maybe 4 along NE-2. I'd imagine US-20 is similar. In Nebraska too the NW corner of US-20 is very nice views of the bigger hills and forests it has.

The Wyoming portion is going to have some dull moments but also some very beautiful scenery. I've driven a lot of Wyoming now and it's quite a wildcard of all sorts of shit imo. Very good state. Also US-20 will lead you up Boysen State Park which is worth stopping at as you go through the canyons. It's a super nice drive. A day down in Teton's is also worth it if you can spare the time while at Yellowstone. Just be aware in summer it's fucking PACKED so parking is pretty tough by any of the popular trailheads. If you want to hike any of it get there very early, otherwise just take the drive through.

In Idaho most of that drive is pretty lackluster. Craters is okay, nothing too insane compared to other places you'll see. If I were you I'd cut north into the scenic mountain routes and zigzag your way through Idaho rather than take 20 which is mostly along them on the flat plain below.

For Iowa also I'd go a bit south on US-30 at least for for the west side to see the Loess Hills