It’s very, very unlikely that the pill organizer will cause any problems, but since you’re trying to anticipate all contingencies, I would suggest that a border crossing with any unlabeled item containing an assortment of prescription pills is not the best idea without some backup documentation, which could consist of bringing the original bottles with the prescription labels, or alternately the information sheet(s) provided by the doctor, hospital, or pharmacy with your name on it listing the medications. Not something to be paranoid about, but having that immediately at hand could save some time and hassles in the unlikely event any questions are asked. Most likely, you’ll just be told to have a nice day, eh? 
So why doesn’t Big Pharma produce individual, daily dosages in blister packs for travelers? I swing by the pharmacy, pickup a vacation length +2 day supply, and head off on my world jaunt.
Um, my pharmacy would do that for a small fee! But when I’m traveling internationally I stick to the letter of it, “original labelled bottles”, to avoid any difficulties. One country might be okay with blister packs, but the next country may not, so I don’t take the risk.
On the way back, don’t bring any flowers or plants. Our niece was held up for an hour waiting for someone to come and inspect them, confiscate them and throw them in a trash barrel.
Realistically, if you’re an American citizen trying to enter the United States without the proper paperwork, you’re likely to eventually be let in. You’re an American citizen, after all. Not having the paperwork is really only like to be a PITA, especially if (unfortunately) you’re not Caucasian.
Heck, some years ago the US customs let in a psycho carrying a bloody chain-saw, which he had just used to dismember an elderly couple in New Brunswick.
His papers were in order.
Interesting things happen at that border there. My mom spent her first two years riding the international streetcar between St. Stephen/Milltown/Milltown/Calais in a basket six part-days a week. At the ripe old age of six, the bunny that she won for dancing on roller skates with a full wine glass on her forehead was confiscated on the Canadian side.
I wonder if they thought it was moose, deer or bear blood, or if they were just bloody stupid.
We had a couple of threads about it at the time.
Here’s the relatively restrained MPSIMS thread, with discussion of probable cause, communications between Canadian and US LEOs, and so on - reasonably restrained, including discussion of how blood stains can sometimes be mistaken for rust: You Can’t Take A Finger Nail Clipper On A Plane, But A Bloody Chain Saw Is OK
And here’s the much longer Pit thread, where people were a bit … less restrained: Keeping US Borders Safe
Any reason the Grand Portage MN / Pigeon River(?) crossing isn’t listed?
I know not every road has a CBP station, but there is one there.
(Some googling says it is busy, but long waits are rare)
Brian
(who has only crossed at SS Marie, on a bicycle)
This site is supposed to include wait times.
Not all crossings keep track of and post wait times; Pigeon River is one of them. It really does exist, albeit lost in time, lost in space . . . and meaning (it was moved downstream from the Outlaw Bridge – built without either Canadian/Ontario or American/Minnesota approval – to be closer to Gitchigumi). Usually it is quite quiet, except when it isn’t, for there is so little traffic that a sudden surge in traffic (for example, outbound skiers, outbound fishermen or returning revellers), or an officer calling in sick, can double your wait time. Paying duty inside is somewhat slow, and depends on the volume of traffic. The Canadian officers are OK (although one once demanded Sven and Ole’s pizza to let me through ). The local American officers are OK (aside from the one who deliberately and tragically shot himself dead at work last year – I wish I were joking, but sadly I’m not), but in recent years they have rotated come-from-afar officers through the post who sometimes are wound a bit too tight.
Morning rush hour southbound during ski season is Saturday and Sunday mornings 8:30-10:00 am EST when you might wait two to five minutes. Take care for winter storms, for they can be fierce along that part of the North Shore.
Morning rush hour southbound on lovely summer weekends is Saturday and Sunday mornings 9:00-10:00 EDT when you might wait five to ten minutes minutes, particularly if there is a festival in Grand Marais.
There is no evening rush hour southbound.
Rush hour northbound in fishing season in the mornings is 9:00-11:00 am CDT when you can expect to wait ten minutes or more.
Rush hour northbound on lovely summer evenings is 10:00-11:00 pm CDT when you can expect to wait five or ten minutes as Canadians return from Grand Marais.
When trying to figure out the time differences, the Canadians in that area are one hour ahead of the Minnesotans in that area, 'cause that’s how the Mounties always get their man.
The smart money is on fueling up during the day or early evening in Thunder Bay or Grand Marais. For gas the only places between Grand Marais and Thunder Bay that are routinely open are at the Grand Portage Trading Post (where you can get convenience store food and nuke it) that closes at 9 pm S-W and 10 pm R-S about seven miles south of the border (with one hell of a hill each way for cyclists, but with a great view of ON, MN and MI from the top), and Ryden’s Border Store that closes at 8 pm about a mile south of the border where you can cache via mail/FedEx/UPS and pick up when you pass through (the Grand Portage Trading Post is also getting into offering this service). If you want a lovely meal, make reservations for the Nanabijou at the mouth of the Brule River in the summer about twenty-six miles south of the border, or any number of places in Grand Marais without reservations, such as the Gunflint Tavern.
Prophetic words – a fellow passed away cycling up that hill yesterday. 
Fun stories about the definition of weapons when crossing the border:
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My wife put forward that we had bear spray as we were going backpacking.
Canadian border guard: Are you planning on using it as a weapon on people?
Wife: No
Canadian border guard: Good. Then don’t and we won’t consider it a weapon, and we’ll let you leave Canada. -
A colleague at my company with a strong Russian accent but a naturalized U.S. citizen was crossing the border to go camping in Canada.
Canadian border guard: Do you have any weapons? guns? knives?
Russian american: I’m going camping so I have an axe…
4 hours later (literally)
Canadian border guard: Don’t declare something as a weapon unless it is or you intend to use it as such. Enjoy your stay.
So be honest but don’t overshare!
Canada has some interesting weapons laws. For regular civilians, It is illegal to carry any object at all with the intent to use it against a person should self defense be necessary. Really. You can’t carry anything for self-defense. That’s it.
The legality of carrying anything is based upon intent (unless it’s outright banned, like switchblades, or regulated, like guns, etc), as you showed.
So, no problem. You are carrying that 14" hunting knife in a nightclub because you are planning to open some letters later, right? Not really. It comes down to what the police and then the courts think was your intent. You can state your intent and they may buy it or they may not. Get a good lawyer.
Strangely, you are allowed to carry weapons for self defense against animals. People, no, but animals, yes. So, if you are a mail carrier you can carry pepper spray to defend against dogs. But not people. And, provided you are a lawful gun owner, you can carry a firearm in the woods strictly for predator defense. But not people defense.
Even stranger is this scenario: It is legal to carry a 12" knife on your hip if you intend to go hunting and are planning to use it to prepare game. If you stop at the gas station on the outskirts of town and you are attacked by a lunatic and do not have the option to retreat, you are allowed to defend yourself to the degree necessary to protect your own life, even if that means killing the person. If necessary, you can use said knife to do so.
So, in Canada it is not necessarily illegal to carry an item that could be used as a weapon, and it is not illegal to use that item as a weapon in self defense, if you must. But it is illegal to anticipate the necessity of self-defense as a scenario that could plausibly befall you and thus plan for it. You can’t combine the two. Strange. Strange, because it is perfectly reasonable to conclude, “You know, I’ve probably got 50-some years left on this marble and the likelihood that, through no fault of my own, I will need to legally defend my life during that time is not zero. Unlikely, but not zero. And I don’t like that.”
You can, however, legally anticipate and prepare for other equally unlikely events. Like buying insurance for you home against a house fire.
I live in Canada and when I go mountain biking I carry bear spray in a holster on my chest. It’s like a little fire extinguisher. Can’t miss it. I ride right from my house, which is located in a 100% urban neighbourhood, to the start of a trail that winds for miles through bear-populated forest. The police do not respond well to those carrying bear spray in urban spaces. But, it is my intent to use it for a legitimate purpose and should I get stopped on my way to the trail I should be ok. I think…
Canadian legal-types, do let me know if I got any of this wrong.
You did not get anything wrong on the legal niceties.
No, I think you’ve got it pretty much correct. Basic everyday things that could be used offensively against people, are only considered weapons if you intend them to be. As you note, there are exceptions (“I’m backed into a corner, and all I have is a _____”), but intent matters.
Another example, not quite like your bear spray example, but something else to consider: I never had any problems carrying my baseball bat openly to office-league baseball games. Oh, I could do a number with that bat–but only to innocent baseballs. Never to a person. That was never my intent. And I never had a problem carrying my bat, even on my way to my car in the mornings, when I went to work.
I’m not sure what the regs are these days, but the last time I checked (a couple of decades ago) mid-sized bear spray cans were OK (big enough to do the job against a bear), but wee little ones to tuck inside your purse or pocket were not (sized for carrying by people for use against people).
Last week Ryden’s had a note on their website warning of a 1.5 hour wait for fishermen entering Canada. I asked the person in charge of the the Canadian side and was told that the rush hour delays the last couple of weekends were about 10 minutes, so put the Ryden’s notice under Trump fake news. Probably just folks caught trying to being guns into Canada without the proper paperwork having to go through thorough search of their persons, vehicles, boats and gear that takes quite a while, and then being turned back to the USA where Ryden’s would be their first stop where they could tell the free world about the Canadian border.
Today I came across an excellent article in Northern Wilds about the Outlaw Bridge Border history—The story of the Outlaw Bridge - Northern Wilds Magazine which was built by Thunder Bay and Duluth folks who were not willing to wait any longer for their governments to build a bridge, so they just went out and built one themselves. ". . . no one wanted federal officials to know about the bridge until it was a “fait accompli.”
Heh, one time on a highway near the southern border there was a checkpoint (i think mainly to look for illegal immigrants even though it wasn’t at the border), where the guard outside the counter made a motion with just his index finger making the “pull forward” motion. To me, that signals “keep pulling forward until I tell you to stop”, so I continued to move forward slowly, but then he kept doing the same one finger motion, but quicker and more forcefully, as if he was getting annoyed that I wasn’t speeding up, so I continued to move, but still very slowly until I was completely past him just in case he did want me to stop. I would have just kept going at a faster rate if he had made the same motion with his whole hand rather than just one finger.
The OP has presumably long-since made the discussed trip, but having just visited Canada ourselves:
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Read up on the possible border crossings. Some Dopers did us a solid and suggested an alternate to the one we’d have used by default (I-89) and reroute as needed. Our crossings (to Canada: westernmost one in Vermont; back to US: an out-of-the-way crossing into northwestern Maine) were both trivially easy. The only other time we crossed the border was about 10 years back - Peace Bridge both ways, I think. Northbound was fairly quick; southbound there was a bit of a backup.
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Prescriptions: I had all mine in pill organizers in my purse, supposedly a no-no, but I also had prescription bottles for all of them in an outside pocket of my suitcase. If they’d gotten snippy about the organizers, I had enough of a supply in the prescription bottles. A hint for the future: if you get your scrips in bulk in mail-order, get a small supply locally, and keep the bottle - that way you can take enough for the trip in that bottle and leave the bulky ones behind.
I don’t know what criteria the border agents use to decide to do a more detailed inspection of the vehicles - assuming you’re not on any Do Not Fly list or similar. Maybe it’s random, maybe it’s when they’re bored, maybe it’s every 10th car or whatever. In any event, we were waved on after the cursory questions: “bringing any tobacco / alcohol, any medication other than personal use, any gifts / souvenirs, any excess cash” and so on.
Passports:
Actually, the law was implemented in 2006 or later. Our trip to Niagara Falls was in 2006 and we did not need passports (though as we had them, we used them anyway).
There is also something called a passport card which is less expensive than a full-on passport; it can be used to travel to Canada and certain Caribbean places by car or by sea, but not by air. It is valid identification for travelling in the US by air, if you are in a state whose license doesn’t meet the newer RealID rules. Of course, if you use such a card for domestic travel, be prepared for highly-trained TSA agents to refuse to accept it.
Gasoline: I think it wound up being something like 4.00 a gallon (if my mental conversion was right) in Canada. We happened to fill up in northern Vermont before crossing over, barely used the car at all in Quebec (except to drive from Montreal to Quebec City), and did not need fuel again until we were back in Maine.