Monktoberfest is one of my favorite conferences to attend. Fresh off the plane, I wanted to share why this is one of the conferences I don't miss if I can help it.
It's far off the beaten track#
It happens in Portland, Maine, in the fall. For folks coming from anywhere west of Chicago or across the Atlantic, there are no direct flights. You can take two flights, or one flight and a bus ride, or one flight and a train ride.
This means travel is a total pain in the butt, but also that the attendees really want to be there. Monktoberfest happens for three days every fall, and it's put on by the good folks at RedMonk, a boutique analyst firm focused on developers. The developer-focused ethos runs through the whole conference, from the talk topics to the way sponsors are handled to the plentiful coffee to the 10:00 a.m. start time.
If you do attend, plan to arrive mid-day Wednesday so you can join the harbor tour. It's super touristy but a fun way to step into conversations while seeing some of the beauty of Portland. And many folks take the whole week and work remotely, or extend their trip over the weekend after.
It's discreet#
You don't know the agenda or the speakers until you show up, though you know the talks are going to be polished, offbeat, and on technosocial topics. They're even secretive about when tickets go on sale. This is relatively unique among tech conferences, which are usually pretty upfront about what attendees can expect.
It adds an air of serendipity and exclusivity, but also fosters community. Similar to the hike to get there, the fact you have to actively pursue tickets without any idea of the speakers means you have to want to go for other reasons, such as the reputation and the other attendees.
One of the organizers described it as what Rands would call a "welcome to our home" type of conference, where part of the point is, as Rands' article mentions: "each conference is a reflection of the care of these organizers".
There are no sponsor booths#
I once talked to our events person about sponsoring Monktoberfest. Her first question was, "How many leads do you think we'd get?" I begrudgingly answered: "zero." There are no booths, just a sponsor shelf with a minimal swag. There's no badge scanning, no spectacle, and no prizes. They do thank sponsors multiple times and display logos on a poster board, but Monktoberfest is 100% a brand-halo conference.
The answer from the events person was basically "Wow, sounds cool. But we can't do this out of my budget." Fair!
For me, the minimal impact of sponsors is a welcome difference. I can focus on interaction with other attendees and the talks. I know how important vendors are for conference sustainability and I take time to visit them; I've learned useful things by visiting sponsors at conferences.
Some folks find sponsor conversations energizing and useful, and others find them distracting or draining. Monktoberfest caters to the second kind of person.
That said, one of this year's sponsors significantly improved my impression of them. The brand halo effect can work, but it's a long, long play that requires hard work as much as money.
The food and beer are amazing#
This isn't just a conference about tech. It's also about beer and food, and both are fantastic. Lunch was a nice conference lunch, but typical. The dinner is another story. Each time I've attended, it's been a buffet of amazing food, beautifully presented. I'm talking sushi, oysters, fancy grits, tacos, and more.
There's also a beer expert at dinner. Ryan shows up with a long list of beers, all interesting, many local. The line to get a beer is long, but that's because he's willing to take time and offer you advice on what you should get; he's practically a cicerone.
The experience is unlike any other conference or event I've attended. Should you not be into beer, there was wine too. I also chatted with an attendee who didn't drink and he said there were non-alcoholic options such as seltzer and soda.
The attendees are great#
There are three categories of attendees: first-timers from the local area, first-timers from elsewhere, and regulars who use the conference as a reunion.
The local first-timers bring a less technical point of view to the conference, even though they are often involved with tech. This year I talked for a while with a non-technical founder who was from Maine. She and her co-founder had used Claude extensively to build an MVP for their edtech application, but finally found a development team to build out the vision in a more sustainable way.
The first-timers from elsewhere go through the travel filter I mention above and tend to be engineering leaders who know RedMonk by reputation.
The last group is responsible for one of the unique aspects of Monktoberfest. The regulars mean that when these folks see each other, there are plenty of smiles, in-jokes and references to past talks. They also foster a culture of thoughtful conversation and respectful attention. But it can also make things a little awkward. The bonds between people who've attended Monktoberfest many times and shared experiences can be slightly off-putting to a newcomer. The first time I attended I felt like a spouse at a high school reunion.
But when I fought my introversion and struck up conversations, people were welcoming and happy to chat. There's also a Monktoberfest Slack where newer attendees without the network can learn about after-hours activities. I recommend joining it.
Since this most recent conference was my second time attending, I felt more comfortable. I had some great conversations with people I'd never met. I also caught up with some former co-workers or attendees that I'd met last time and interacted with online since.
Monktoberfest has an explicitly blessed "hallway track", full of conversations about what is working and what isn't. The long breaks, small conference size, and the well-attended dinner foster discussions. So do the talks.
The talks#
Can you believe you've read this far and I haven't mentioned the content, which is typically front and center when it comes to conferences? I'm doing the speakers a disservice, to be honest. Let's remedy that.
Monktoberfest is a single-track conference, and the talks are all technosocial in nature. As far as I can tell, there isn't really a conference theme other than "be thought-provoking".
What does that fancy word, technosocial, mean? You'll hear talks of interest to nerds and technologists, but they won't be super tactical or focused on a specific technology. No topics like "check out the latest cool library for Rust" or "when should you consider JMS vs Kafka". They're thought-provoking bigger-picture talks instead, tying technical concerns to wider perspectives, such as health, ethics, or society.
To give you a taste of what I mean, topics this year included:
- burnout and how to avoid it
- what technologists owe others when they build AI
- educating the next generation of developers
- endometriosis and the state of womens' health
- what towns in Maine can teach us about identity
While it is hard to narrow it down, I had two favorite talks this year.
One was an impressive, funny rant about systemic complexity and the abstractions that give software such power. I know, I know, seems dry and boring but trust me, it wasn't. The other discussed community efforts to build a bike bus for schoolchildren and how they can inform SREs' efforts to improve legacy software systems.
If I had to pick one takeaway from this year, it's that AI is being recognized as a powerful tool for building software but not a cure-all. Just as there's a backlash in the USA against data centers and the overweening aspects of AI companies, attendees had reservations about AI in the workplace and in society. There was discussion of the many ways AI can be helpful as well as ways it can be problematic and even distressing.
If you want to get a feel for topics over the years, here are the YouTube playlists for past conferences:
You can also glimpse the conversation between attendees by viewing the #monktoberfest hashtag on Bluesky.
Should you go?#
Are you looking for a conference in a remote, beautiful part of the United States? Do you want your mind bent with big-picture talks with a technical tinge? Do you like insightful chats with people from both tiny startups and giant companies like Oracle, AWS, and Google? Then Monktoberfest might be worth the trek.
