The Art of the Long Weekend

I don’t like to be rushed. Sometimes I will rush by choice, but I don’t like to have rushing forced upon me. So going out of town on a long weekend needs to be strategically planned so that there is no rushing but also no boredom. Three days is too little time for a real vacation. All you’re looking for here is a little breather, a little break from the everyday.

The key is to go somewhere no more than two hours away. This allows you to get there early enough on Friday night (or Friday afternoon, if you’ve got one of those forgiving workplaces with early dismissal before a long weekend) that you’ve got time to settle in and have a nice, leisurely dinner, and to get home on Monday early enough that you don’t feel like you’re racing right from vacation back to the office.

(Aside: My esteemed colleague here at Go Go Go would say that no road trip should ever be longer than two hours. Having grown up with two-week-long road trips with my family every summer, I have a much higher tolerance for that sort of thing. But for a weekend trip, she is absolutely correct. Two hours. Two and a half, maybe.)

Now that you’ve got a radius to work within, you have to consider what you actually want to do. We’re based in Chicago, so within two hours we could get to Milwaukee for a brewery tour, a little bit of art, and some better-than-average brunch. Starved Rock State Park is another option, heading south for camping and hiking and maybe a pontoon trip. Or you could swing around to New Buffalo, Michigan, to see the lake from the other side, search through antique shops, and of course lose a ton of money at the casino.

This beautiful lake is exactly two hours from Chicago in Potato Creek State Park, Indiana.

It’s easy. Find your town, draw a circle, and then just pick a direction. There’s probably something there at the end of the road.

And then the most important part about the long weekend: you have to balance between the twin ideals of a) relaxing and b) doing enough stuff so that when your coworkers ask on Tuesday, “What did you do for the long weekend?” you’ve got an answer that’s not, “Ehhh… I re-watched the entire run of Party Down.” If you’ve got one “thing” you plan to do each day (brewery tour, art museum) and then one other thing you could do that day (river boat trip, neighborhood festival), you’re all set. In between that you’ve got to eat, so find a couple of good options for each day, one breakfast-y and one dinner-y, and then allow yourself to go someplace completely different if something else catches your eye. Also, allow for sleeping in late and taking a nap—the things you’d love to do any day of the week but can’t.

As Americans, we’re kind of screwed in the vacation and holiday department. Most of us only get two or three long weekends throughout the year that aren’t big family holiday obligations. So make the most of that extra time. With a little bit of planning, you’ll have fun, relax a little, and inspire awe and jealousy among your coworkers come Tuesday.