There’s a festival every month in Annapolis. Some favorites: Annapolis Restaurant Week, which offers up prix fixe menus and a chance to eat at some of the town’s fanciest restaurants on the cheap; May Day, where local businesses put out gorgeous, themed flower baskets with the hopes of taking home the top prize; the Halloween Festival on Maryland Avenue, complete with dog costume contest; the Maryland Renaissance Festival, which features a full-size Renaissance village and tons of performances, shops, and delicious food vendors; the world-class Annapolis Film Festival; and our winter favorite, the Midnight Madness shopping extravaganza.

Love watching the productions of the King William Players? Expand your drama horizons with shows from the Annapolis Shakespeare Company, the Ballet Theater of Maryland, Live Arts Maryland, the Annapolis Opera, the Colonial Players Theater, and the frequent offerings from the Maryland Hall for the Creative Arts. If you happen to be around over the summer, check out a show in the Annapolis Summer Garden Theatre. (And don’t forget—nearby Baltimore and DC are teeming with opportunities to see shows.)

If you want to take to the stage yourself, there are also opportunities to take classes in performing arts offered by the Maryland Hall for the Creative Arts.

Walking down West Street, it feels like you run into an arts space every few steps—whether it’s the Annapolis Collection Gallery, a space devoted to acclaimed local artists across mediums or the fancier Rams Head On Stage, a music venue that draws national names. The Maryland Federation of Art, headquartered in Annapolis, showcases local art and artists in its Circle Gallery and other local spaces. Many restaurants in town, too, act as unofficial galleries and performance spaces, hosting live music every weekend (from jazz and singer-songwriters to traditional Irish sessions and punk rock) and showcasing local works on the walls. Want a more hands-on approach? Take a lesson at Art Farm Studios or get on stage at an open mic night at the Metropolitan.

Look—we all love Target, but there’s just something special about going into a little boutique and checking out a curated collection of items. Main Street and Maryland Avenue are the perfect places for a little retail therapy. Hunt for gold at antique and vintage shops, find something to wear to the next Waltz Party at one of many boutiques, buy some non-Program reading material at a bookstore, or enjoy a selection of wares from all over the world at the new fair-trade shop on the corner. If you do need to do the big box thing, Westfield Annapolis is a massive mall with 210+ brand-name stores, and nearby Annapolis Town Center has the classics: Target, Whole Foods, Bed Bath & Beyond, and more.

Annapolis offers a ton of options for Johnnies to explore, but if you’re looking for something with the Johnnie stamp of approval, you’ve got to hit Old Fox Books or Galway Bay. Old Fox Books is a charming bookstore on Maryland Avenue with a great selection of texts (including brown-paper wrapped “mystery date” books), a great coffee shop with a wide variety of tasty options, and the cutest back porch in the world—there’s even a magical little fairy garden where kids’ storytime is held. For Graduate Students, the must-hit is Galway Bay, an Irish pub that’s also located on Maryland Avenue and is the perfect place to grab an after-seminar pint and keep the conversation going.