Top 10 lessons learned from a five-day bike and poker trip

Last week, I took a five-day, four-night bicycle trip around Massachusetts and New Hampshire. On three of those nights, I stayed at friends' houses and played in their home poker games.

It might sound like a strange idea to a lot of people, but for about a decade, I've dreamed about taking a cross-country bike trip and playing in home poker games along the way. Anyone who has spent any time reading my column over the past nine years knows that I love home poker games. I also enjoy cycling, though I'm more of a "get a 1-2 hour ride in for fitness reasons" type of guy than someone who goes out and races.

Combining the two would be great fun and would make a great story, perhaps even generating enough material for a book. What's more American than the home poker game? And seeing the country in 12- to 15-mile chunks every hour would give me a chance really digest the experience and see the nuances of every region I travel through.

Logistics for such a trip will be tough to pull off. Taking 8-10 weeks away from my family would be hard — being gone for just five days last week was pretty tough — but my wife supports the idea, and even thinks tagging along with the kids for a few weeks in an RV to meet up on nights I'm not playing poker would be a great adventure.

I had a blast on my 275-mile tour last week, and while I'm not ready to get my sore butt right back on the road, I'm more excited about the concept of a cross-country bike/poker tour than ever.

The real reason I'm glad I took this mini-tour, however, is that I learned a lot about what I'll need to do to make a longer trip a success. Here are the top 10 lessons I learned from last week's adventure.

10. Get a new bike
My 12-year-old Diamondback Outlook just isn't going to cut it on a long tour. I got it tuned up a week before I left, and by the time I got home, it was in pretty rough shape. I had a rear pannier and a BOB trailer, which are both great for hauling gear, but that bike just isn't cut out to handle all that extra weight. Add the expense I'd incur getting a handlebar setup better suited for long days, and I'll be better off just getting a bike intended for touring.

9. Pack smarter
I was in a bit of a hurry when I left on Tuesday afternoon. I had a few errands to run in the morning, and they took longer than I had expected. I had told the host of the first game I was playing in that I'd arrive at his place around 5:30, and I had 45 miles to go to get there. I ended up rushing around, throwing things into my pack without a whole lot of planning.

As a result, I brought a lot of things I didn't need and left a few things at home that it would have been nice to have. For example, I brought at least three shirts that I didn't wear, and left my Leatherman — which would have made pulling a small metal filing out of one of my tires a breeze — at home.

More than anything, I'll be trying to pack a lot lighter. When I started out, I was pulling 68.2 pounds of gear (including the weight of my pannier and trailer), which made every climb harder than it needed to be. I quickly learned that filling my 10-liter water reservoir to the top was a bit excessive. Filled to the top it weighed 20 pounds, but I rolled through a town just about every hour, and people doing yard work outside were happy to let me top off from their hoses outside their house.

8. Play with people who are excited about the project
I've talked to a lot of people about the possibility of a cross-country version of this type of trip, and most think it's an amazing idea. Many have asked how they could help and offered to get me in touch with friends across the country who have established home games. Getting buy-in from folks who want to be involved in the project makes the prospect of playing with them much more exciting than playing with random people who are just looking to fill a seat in a game.

7. I'm not the story
I spent a lot of time during this trip explaining to people what I was trying to accomplish. As I said above, most were pretty excited about it. After a while, though, I tried to steer the conversation away from my trip. The goal is to get to know the character of a home game — to understand the people who play together and the community they have built — not to spend the whole time talking about how many miles I biked or how sore my legs are.

6. No game is set in stone
My original plan for the trip was to play in a home game every night of the trip. A week or two before the trip, someone who had planned to host a game told me his game had fallen through due to a lack of players. Another game was in jeopardy of falling apart when two players canceled less than 24 hours before the game was set to begin. (We ended up playing five-handed.)

If I end up changing my route on a cross-country tour to get to a game, only to have it canceled, I'm going to have to roll with it. People's plans change, and sometimes a poker night that seems like a sure thing might get called off.

5. Game hosts are pretty amazing
Most people who host poker games (the legal, non-raked kind) aren't looking to make money on the endeavor. In fact, most people probably lose money on the deal. They buy food and drinks to make their guests comfortable and spend untold amounts on cards, chips, tables and chairs. Some have rooms entirely dedicated to poker, and they love to get people together for a game.

The three people who hosted games for me put games together specifically because I was coming to town, and I've had people I've only met through poker forums reach out and say they'd get a game together if my route goes through their town. It's pretty incredible.

4. Schedule more downtime
While I was originally disappointed to not be playing poker all four nights of my trip, the night I spent camping out alone at the Harold Parker Woods was actually one of the highlights of the trip for me. It gave me a chance to reflect on the experience to that point and do some reading and writing.

I also passed a bunch of spots where I would have liked to spend more time. I didn't even dip a toe into the ocean at Hampton Beach in New Hampshire, nor did I have time to stop in and look at Henry David Thoreau's cabin on Walden Pond in Concord, Massachusetts, despite passing right by.

Having time to visit cool places and write and reflect would be an important part of a cross-country trip for me, and I don't want to feel harried into racing from one game to the next just to maximize my time spent on the felt.

3. Play with the grain of the game
One of my only regrets I have from the trip was calling Mini-May late one night when it was just the host and one of his guests remaining. The five-card stud game with a community card and a replace is a staple in our home game, but neither of the two other players in this game had played it before. One in particular made some pretty big mistakes, because he had no idea how to play. He recognized them after the fact and was mad at himself for making them, but I felt bad that I'd convinced them to play the game, and then taken a few pretty sizeable pots off them.

It's one thing to introduce a game to one or two new players at your own home game. It's another thing entirely to do it when you're the only person who knows how to play it.

The goal of my trip wouldn't be to book the largest profit possible (though finishing with a profit would be nice), it's to get to know the culture of different home games across the country and get to know the characters who play in those games.

2. Don't play too late
My paternal grandfather always used to say "Nothing good ever happens after midnight." For the most part, in my life experience, he's been right.

During my trip, I played pretty well in the games I attended. But two major missteps turned what would have been a profitable trip into a losing one. Both mistakes happened after midnight, and both were glaring errors. So bad, in fact, that the one player who witnessed both nicknamed me "Gremlin" and said I shouldn't be allowed to play after midnight.

I won't bore you with the hand histories, but suffice to say, the play was terrible. I was super fatigued from long days riding the bike and not enough sleep, but part of good decision-making at the poker table involves knowing when playing conditions are not in your favor. Playing late at night was not ideal for me, and I should have called it quits earlier on.

1. Do it for charity
While this isn't really a lesson from the trip, people I talked do during my tour helped solidify my plan to play for charity. I'm thinking of crowdfunding my bankroll and donating whatever I have at the end of the trip to a charitable cause that's meaningful to me. I think it's a great opportunity to raise awareness for an issue, while also helping showcase the nature of home poker games in the United States.

I have some ideas in mind, but suggestions are always welcome. Ping me @CasinoCity_AT on Twitter and let me know what you think!