Asklemmy

I don't really have any ideas, but I want to warn you, you might be about to get into a fight you can't win. The town is probably so picturesque as the result of tradition and liberal application of ordinances. Don't let that discourage you, I'm just saying to keep that in mind when making plans.

Let me know when your karaoke/trivia night is?

Also, welcome to Ottawa.

Three words:

Bizarre public art!

Walk around in a bigfoot costume at night.

I live in a small city of like 33k, and basically, why is it a snooze fest? Because the population is mostly 9-5 and with families or older people. There is stuff to do, but it isn't centered around the 20 somethings. That kind of thing is for the bigger cities or college towns.
I can tell ya that for someone like myself, the bar scene doesn't fit who I am today. It fit me back in my 20s, but that's because I wasn't super healthy, mentally. Something to think about

9 and 10 are early ?

Off the top of my head:

1. Start researching your local ordinances and bylaws. Like someone mentioned here, there might be a reason your town dies after 2200.
2. Think about the kind of things you want to see in terms of nightlife. Does that mean live music? Block parties? Techno night at the clurb? Kink stuff (seriously)? Theatrical performances? Hash and coffee socials (sort of a joke, but thinking through the logistics of such a thing has been my daydream du jour recently)? Etc.
3. Find others who would be interested in the kind of stuff you'd like for nightlife activities. Start talking $ and logistics - are there any grants you could try and apply for? Fundraising activities? Where are you going to do this stuff? What do you need in terms of insurance? Do you need to address any pesky bylaws, and can start working with your local government to try and tackle that? And so on.
4. Make a plan and act.

The big starting point is really just defining one or two things you want to see, and working to get to the point where you see them. In the course of this you might be surprised by what you find (someone mentioned good ol' Ottawa, ON as an image of the place you're describing - but there's actually a decent amount of stuff, both above- and underground, you can find when you start poking around).

How close are these surrounding towns? What's the population, particularly for the demographics you would appeal to?

Often, it's not worthwhile to bring your favorite culture to your home. Just go to the culture where it already exists. Often, these quiet, boring places are populated by people that WANT to live in a place that's quiet and boring. It doesn't make much sense for anyone to move there if they don't.

I know a dude who moved to the town I live in. He couldn't find a place where people like him hang out. So he created one. It grew into a bar. A lot of people loved that place. He just recently closed it after 13 years.

Do you feel making friends is hard because your lifestyle is not common there? I can't quite tell what you're saying OP.

If you can manage to get some space somewhere or get people to contribute space, you could have artists in residence. Often artists want to get away and just have a chill place to focus for while, like a week. They can show what they made in a small personal exposition.

Grow mushrooms and give them away

Bring neighbours together. One step at a time.

The problem with a lot of small projects in towns is that they cater to a certain crowd - but there are often not enough people to sustain that momentum for a longer period of time. And it's sometimes used to keep people away. (Aka the soccer fans go to their club, the old folks to bingo, the Christians to their "clubhouse", the D&D to theirs. And in the end small bubbles form)

So organise something that caters to "basically everyone".

I once lived in a neighbourhood that suffered from exactly this problem until a few people (one had actually a research background in this matters) started a small initiative which did exactly this: bring the neighbours together with some things people hardly can be opposed to. First they rented a proper Pizza oven and did a "pizza festival". They "sold" the dough,tomato sauce and baked the pizza, but you had to bring your own toppings (saved them from the ongoing debate about that). Someone volunteered to get the older folks to the location (a cul de sac). Proceedings did not go to any cause beside the festival itself, they only covered their cost.

Next time they organised a outdoor movie night with a -intentionally non-confrontational- movie from the 80ies.

Etc. Etc. Other neighbourhood followed with similar concepts.

Now multiple neighbourhood bought a mobile pizza oven together and gifted it to the city so that it can be used by every neighbourhood. Etc.

But this was their way to bring people together beyond their interests/hobbies.

And it worked.

A club what are your interests? Create a club based around something you're interested in.

Let your best friends show you to everyone in town wearing a salmon suit.

Sounds ultra white. Make a bunch of not white friends and bring them there. That'll make things pretty interesting