Good Transit is Fun

That’s right, you heard me.

6 minute read

December 18, 2025, 5:00 AM PST

By Joshua Woods


Festively decorated holiday train in Sydney, Australia.

Chayut Orapinpatipat / Shutterstock

This column is a delightful bonus installment of an eight-part series in partnership with Chicago-based transit planner extraordinaire Joshua Woods, who authors Thoughts About Cities. Titled “Transit Planning 101,” it’s the transit planning boot camp you wish you got in planning school. Learn more about Joshua and the inspiration for the column, and read his other installments here

An excerpt from my recent Planetizen column, “What is Good Transit”:

This is by no means an exhaustive list of what makes Good Transit, but a transit authority that provides service that is available, reliable, fast, and safe is probably providing what its passengers would consider Good Transit. 

Honorable mentions:

  • Good Transit is fun. The Kansas City Streetcar Authority hosts the KC Streetcar Holiday Jam annually, with live musical performances on select trains.

So I might have buried the lede a little bit about my being a part time bus driver. Some of the buses that I drive are actually replica trolleys. I’ve even done the whole narrated sightseeing tour gig complete with the ugly headset, and stuck-in-traffic banter. Yes, there is a bell and, yes, I will ring it. Happily.

Two of the types of trolleys you're likely to catch me in
Two of the types of trolleys you're likely to catch me in

There are plenty of good reasons to charter a bus. If you’re planning an event where a good number of people are all going to the same place, a bus might be the easiest solution. You immediately throw out ~30% percent of the utility behind those reasons once you reach for a trolley. Yes, the vehicle is nostalgic and kitschy, but those wooden seats are hell on your back, the thing hits bumps with everything it's got, it’s 90 percent blind spot, and there’s a reason you rarely see them going over 40mph. People rarely want to open the sides to make it an open air experience because it’s either too hot, too cold, or too windy.

Still, after driving trolleys for the past few years, it still amazes me how reliably people go crazy for trolleys. If I pull up in a climate controlled J4500 bus with reclining leather seats and tv screens…

Large white charter bus
…like this one

…I might get a “nice bus,” particularly if it’s a brand new bus. I can pull up late in a trolley in nearly any condition and people go NUTS. Particularly vocal subgroups include kids, parents looking for free/cheap things to do with their kids, older people and drunk people.

Why do people love trolleys? Because trolleys are fun.

More than that, trolleys signal that something fun is about to happen. However serious you think your day is about to be, take it down about 15 percent because you’re about to get on a ridiculous vehicle, and likely do a ridiculous thing.

The company I drive trolleys for also operates regular commuter shuttles between office buildings and the commuter rail stations serving downtown Chicago. These shuttles typically use refurbished transit buses or motorcoaches, but occasionally, we’ll have to throw a trolley on a route to cover for a downed bus (a bus is a bus after all). When this happens, it’s rewarding seeing the passengers, maybe downtrodden by the past 8 hours, perk up when they realize their bus ride to the train is going to be a trolley ride today. Even if it gets a little cold, or their hair does get blown about a bit, once they’re back home, maybe under a blanket with a warm beverage, they’ll probably reflect on the fact that they had an impromptu trolley ride and smile.

Green and yellow trolley moving down street as seen from a crowd on the sidewalk.
The first time I saw the trolley that I would eventually drive
Staging for a shuttle service to/from the Summer Smash Music Festival (this was a mess, but we had fun)
Staging for a shuttle service to/from the Summer Smash Music Festival (this was a mess, but we had fun)
A historical cemetery tour I was chartered for. Fun, if not a little macabre
A historical cemetery tour I was chartered for. Fun, if not a little macabre
A Holly Trolley Bar Crawl in Blue Island ft a very special guest.
A Holly Trolley Bar Crawl in Blue Island had a very special guest.

A lot of the discussion around public transit in the United States centers around providing the transit service that people need or, lately, preserving the service that currently exists, because people need it to get around. In our pursuit of transit that people need, we often overlook the transit that people want. In a moment where we’re asking the public to pitch in a few more of their hard earned tax dollars to save transit, there’s easier political capital to be found leaning into what people want, than projecting a version of what they need onto them. If people want a trolley, then tastefully give them a trolley.

Aside: I think this is where microtransit shows value. It leaves people with a broader view of what public transit can be, and, if done well, a positive association with transit. Throw in a gimmick like cute little electric GEMs around a cute town square, and you’re getting dangerously close to fun.

The limits of a gimmick

I think gimmicks get a bad rap. In its most benign form, a gimmick is just a tool for drawing a little attention. A little razzle dazzle for the people. A tchotchke. For a well run transit authority delivering Good Transit, a tasteful gimmick, like a tourist-oriented route that operates trolleys, or a super artistic bus wrap, or a fully electrified bus route or two, signals that they can provide high quality transit service, with a little razzle dazzle.

Conversely, for a poorly run transit authority not delivering Good Transit, a gimmick signals more of the same...

Shenanigans GIF

If, in your pursuit of making transit fun, you find yourself questioning a gimmick, here’s my guidance:

  • Make sure there’s something worthwhile behind the gimmick. People don’t dislike a gimmick. They dislike being ripped off. At the end of the day, people just want to get there. Someone attempting to rely on transit that is NOT reliably getting them where they need to go, is not going to be amused by a gimmick. Worse still, someone that tried transit on account of a gimmick and found themselves stranded might make up their mind on transit for good.
  • Don’t overdo it. One tchotchke is a cute lens into your background. Fifty tchotchkes are eclectic at best, tacky at worst. To continue with trolleys, some transit agencies, in an effort to make their system feel fun and cool and approachable, will run all of their routes with trolleys. This approach often overshoots fun (especially if the trolley comes hourly) and threatens a maintenance nightmare. Trolleys are a specialized fleet with unique maintenance requirements. They also represent vehicles that might not be interoperable throughout the system. Make sure you have the maintenance bandwidth to support this before making a decision like procuring a fleet of trolleys. In general, if the gimmick threatens Good Transit, it’s not worth it.
  • Make sure your people actually think it’s fun. This gets down to knowing the public that ride the system, and bus drivers that drive the routes. I mentioned earlier that people go nuts for trolleys. I’ll admit, I was being a bit hyperbolic. While most people go nuts when I pull up with a trolley, there are days I pull up and the people get on without a word about it. It just doesn’t do it for some people, and that’s fine. Learn what reads as fun in your community. The fun part? This advocates for experimentation and iteration.

The ultimate example of good transit being fun

I frequently end my I Hope This Helps roundup pieces with “a moment for whimsy,” where I try to share something lighthearted and unserious I encountered that reminded me to leave space for levity. I do this to combat the impulse to assume that serious times require serious solutions that must come from someplace serious. A wise oracle once said, “I learned early on — don’t take life too seriously. There are things you should take seriously like loving yourself, allowing other people to love you, which is a big one. Most of the other things are really not that serious.”

In that spirit, a master class in blending Good Transit, gimmicks, and fun. Disney Transit.


Joshua Woods

Thanks for reading! I am a professional transit planner based in Chicago, IL. I’ve worked at a mix of consulting firms and transit authorities, in both planning and operations positions. Currently the Regional Planning Program lead at the Northern Illinois Transit Authority (NITA). 

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