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9 Things Thought Catalog’s Chelsea Fagan Wants You to Know About Annapolis

From Maryland's state dessert to must-visit restaurants and stores.
Photograph of Chelsea Fagan by Andrew Propp.

Chelsea Fagan had barely left her Annapolis home when she began writing for Thought Catalog, a four-year-old web magazine geared toward millennials that today draws about 20 million US readers a month, according to Quantcast. (People.com gets 14 million.) Fagan promptly became a recognized authority on topics like “How to Ruin a First Date” and “4 Drunk Conversations I Need to Stop Initiating,” meditations that informed her 2013 book, I’m Only Here for the WiFi and that have marked Fagan, 25, as a voice of the sharing generation. (“I write my stuff, and sometimes yours,” reads her Twitter bio.) Though she now lives near Thought Catalog’s headquarters in Brooklyn, she gave us a characteristically unapologetic tour of the Maryland capital.

Start with a meal

“Not to take away from the crabs and corn and Old Bay, but I like seeing Annapolis go from a toy-box sailing town to a destination along with Washington and Baltimore. Vin 909 Winecafé is one of the restaurants really trying to change the culinary landscape. It feels good to come back and see things getting better.”

Photograph of The Pink Crab by Kristen Campbell.

Don’t think it’s all yachts and preppy kids

“In high school, I was in a lot of community theater at Colonial Players, like The Battle of Shallowford and The Busie Body. I identified with the people there more than the WASPy types at Annapolis High.”

But the Pink Crab is kind of irresistible

“Lilly Pulitzer is the Limited Too for adults. I love bright colors, so I naturally gravitate to it. It’s a love/hate thing.”

While in the capital, consume the official dessert of Maryland

“The multilayered, cream-filled Smith Island Cake is one of my favorite desserts of all time.”

Join the morning shift for sunrise at City Dock Café

“After high school, I worked at City Dock Café down by the harbor and started at 5:30 AM. I could see the sun come up over the water. It was a nice way to start the day.”

Everyone should date a “mid” at least once

“I love myself a midshipman. It’s a rite of passage.”

Smith Island Cake. Photograph by Flickr user Jane Thomas.

Then go find a Johnnie

“The very popular St. John’s date would be to go to Annebeth’s, around the corner from the college. It had food, booze, and DVD rentals. You’d get an obscure film, some cheeses and ice creams, and go sit on your couch.”

Carry two fake IDs

“I had two Ohio IDs, knowing they would get taken. The bouncer at Armadillo’s Bar and Grill took one and put it on the wall.”

When you’re legal, hit Pusser’s

“Pusser’s Caribbean Grille has these drinks called Painkillers—it’s like a Chinese restaurant, picking your level of spiciness from one to five. Here, you pick your level of drunkenness. And when you’re 21, you’re like, ‘Six!’ ”

This article appears in the November 2014 issue of Washingtonian.

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