The 2014 Head of the Charles Regatta is this weekend, October 18 and 19, but you’re likely already in prep mode. Whether that means deciding when to go and how to get there, hunting out the best bridge to watch from or taking it all in by map, the Head of the Charles is fast approaching and, this year, the festivities will be extra special as the Regatta celebrates its 50th anniversary.

To provide some color to the Head of the Charles this weekend, we’ve done the duties of gathering together the cast of characters you’re bound to run into at the Regatta (other than the obvious teams of rowers). You want to be on your toes the entire time, after all, and it’s also fun to try to spot every stereotype, given that watching boat after boat go by can get a little boring. Oh, and obviously be sure to look out for Olympians – that’s a given.

So, slip into your Sperrys and settle in: Here’s who you’ll meet this year at the 50th Annual Head of the Charles.

The Overly Enthusiastic Parents

So, your son or daughter has made it all the way as a collegiate rower. We’re very proud of them, too, Mom and Dad. These parents are ruthless, and will do anything to make sure they have the best spot for photo opps as their kid finally rows by the bridge they’ve been camped out on since dawn. They’ve made signs, they’ve brought everyone from Cousin Ned to Grandma Betsy, and they’ll make it very clear to everyone around that that’s their baby out there! Whatever you do, do not engage in conversation, unless you want a recount of every move their little rower has made in the trek to becoming the fifth seat in Cornell’s Mens Eight boat. Don’t get in their way, either: Hell hath no fury like a mother whose view you’ve compromised.

Probably wearing: Head-to-toe gear from the college they’re rooting for, sensible shoes, maybe even a button with their kid’s face on it.

The Swag-Touting Startup Street Teamer

If you’re not careful, you’ll head home from Head of the Charles with branded sunglasses, water bottles, promo codes and other sorts of junk falling out of your pants, jacket and boat shoes. The startup scene is bustling in Boston, and the new companies see the Regatta as a way to get the 400,000 spectators on board with their sick new product or service. They’ll be sending street teams out on the field to spread the word about (insert buzzy, one-word name here), and how it plans to disrupt (insert currently unchanged industry here). Whatever you do, don’t make eye contact with these 20-somethings.

Probably wearing: A T-shirt with the company’s name printed in a modern, minimalist logo, jeans and the smile of not-yet-uncrushed dreams.

The Alum Who’s Still Living in the Glory Days

How do you know someone used to row for Harvard? At Head of the Charles, they’ll be sure to tell you, with an air of smugness that was their attempt at modesty. This person can be found lingering around the Alumni Tent, drinking beers (because now he can, he’ll announce) and bragging about his previous PR on the Charles. He’ll hunt down rowers and try to give them tips on their technique, go on about how he wishes he still had time to get out on the water and incessantly bring up Head of the Charles ’95.

Probably wearing: The same crew jacket from college (can you believe it still fits?) and a class ring.

The Drunk Harvard Fan

Harvard’s football team faces Lafayette at home on Saturday, October 18, at 1 p.m., and the Lower Allston stadium more or less looks over the Charles River. A storm is brewing, you guys, and drunk and rowdy Harvard fans are bound to flood the Head of the Charles likely both before and after the game. After all, what’s a better place to tailgate than a 400,000-person party? Beware of the bros who are lined up along the river, cheering hard for the rowers with intoxicated abandon as they hide their beer cans in their hoodies.

Probably wearing: Crimson body paint, no shirt.

The Person Who Has No Idea What’s Going On

Somehow, there are people in the city who might not have any idea that the Head of the Charles is happening this weekend, or maybe they simply underestimated how big of an inconvenience it might be to usual pedestrian traffic patterns. They’ll be attempting to visit Harvard Square or the Esplanade for a Saturday stroll, and end up in a thicket of slow-moving crowds, looking both horrified and intrigued at the same time. After feeble attempts to shove by and elbow through, they’ll resurrect to trudging along with the crowd, huffing and texting a friend that “there’s a TON of people on the esplanade for some reason?” *Distraught emoji*

Probably wearing: Impractical shoes, the impatient air of having somewhere better to be and having had to be there 10 minutes ago.

For our complete Head of the Charles coverage, click here. We’ll see you on the river!