Ah! It's definitely neat that you go the easier way before getting your starter and a harder way after - it's like the beginning of Kalos, but parts of the same Route instead of a Route 1 that's totally empty, haha.
I have a few suggestions to offer, though!
The first thing that sticks out to me is that your Route is
really wide-open - I would definitely tighten the borders you have so players are reined in a little closer to the main path! Since it's already a pretty long Route, you want to be careful that players who are driven off-course still have somewhere to go, like a small detour to navigate around grass and then come back to the main path, or a small side path that leads to an item, rather than the entire already-large route being open.
Narrowing it down a little also helps you as the developer to make sure players don't miss things - for example, right now, if you place any NPCs, it's extremely likely that players won't notice them; there's no grass that players have to go through, but also no reward for going through optional grass; and any Trainers you place can be easily walked around with no alternatives. Usually, it's best that if you have avoidable Trainers or grass, there's still some benefit to facing them (like giving the choice between a Trainer or grass, rather than making neither one necessary, or placing an optional Trainer to block an item, rather than letting you just walk around them or not having anything past them!).
As it stands, it looks like you'd have a hard time cutting players off from any particular part of the route, so it makes the whole thing feel like you can just walk in a simple line to the end!
My suggestion here: for the east-west segments, try not to give the players more than six to eight tiles to walk vertically (you can alternate if you want it to look natural and not like a straight line), and for the north-south segments, try the same and give players only eight to twelve tiles to walk horizontally - a limit like that would help you give direction, so any detours you make (for optional Trainers and items, for instance) will stand out more to players and be more manageable for you as the developer rather than giving players a sense of not having any direction. (Side note: the reason different directions should have more or less room is because of the screen size - you have more room side to side than up and down, so the path widths usually reflect that!)
Another thing is that all of the grass is optional! Again, this usually works better if players have something to seek out on the other side of the grass, or in the middle of the patch; if, as you have it, they can just walk all the way around it and there's nothing that forces them to pass through it, most people will just skip it entirely! If you do narrow down the main path, I would put some grass directly on it so players have to go through it - at least eight or so tiles would be good in my opinion! (The first Route usually has a fair amount of grass that you're obligated to cross!)
I do kind of agree that the plantlife, although you tried to make it more natural, does lean more towards confusing than pretty - especially on the top right, where there are a lot of gaps that the players can walk, so it's more intrusive to comfortable movement in that area than it serves as a barrier from moving at all.
If you want to scatter your trees a little more, I would do something like Kalos (
example), where there's a
darker kind of grass where the player can't walk - it's visually distinct from normal grass and it's consistent, so players learn pretty quickly that they can't walk there, while you can scatter your trees rather than turning them into walls. It's a win-win, really! And I think it works better than having a different kind of border on every side of the map - especially since some of the tiles you're using (like the log and stumps you pointed out) aren't
meant as cohesive wall-barriers, but individual obstacles, the spacing between them makes it a lot weirder for a player than something that isn't broken up like a designated "unwalkable" grass tile or wall of trees.
Last thing! I don't think it matters what order you map your areas, but I think it helps a lot if you sketch them all out before you start mapping any of them so you have a clear idea of how much to space things out. For instance, part of why your paths are so wide is probably because you weren't sure where they would connect - if you sketch out all of the connecting areas together and have a better idea of where the maps will connect, you'll have a much easier time narrowing those paths to make them work for gameplay!
