Arts + Entertainment
You can’t read your Program books all the time (okay, well, you probably could). When you want to get off campus, Annapolis is at the ready with a thriving arts and entertainment scene. See a play, catch a show at one of the many music venues, indulge in a little retail therapy, check out the art in one of the 25+ galleries, or stop by classic Johnnie spot—Old Fox Books. The West Street Arts District is the cultural hub of the city, but there are plenty of arts offerings on Main Street, Maryland Avenue, and down at City Dock. The best part? It’s all within walking distance. Oh, and don’t miss out on some of the city’s great cultural festivals—three words: Chocolate. Binge. Festival.
Festivals
The Maryland Renaissance Festival. The Oyster Festival. The Chocolate Binge Festival. The First Sunday Arts Festival. Annapolis Film Festival. Restaurant Week. In Annapolis, every season is festival season.
There’s a festival every month in Annapolis. Some favorites: , which offers up prix fixe menus and a chance to eat at some of the town’s fanciest restaurants on the cheap; , 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 which features a full-size Renaissance village and tons of performances, shops, and delicious food vendors; the world-class ; and our winter favorite, the shopping extravaganza.
Theater
All the world’s a stage—and Annapolis has several to boast about.
Love watching the productions of the King William Players? Expand your drama horizons with shows from the , the , Live Arts Maryland, the , the , and the frequent offerings from the . If you happen to be around over the summer, check out a show in the . (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.
Art + Music
With more than 25 galleries and just as many music venues, Annapolis is a hub for all kinds of art.
Walking down , it feels like you run into an arts space every few steps—whether it’s the , a space devoted to acclaimed local artists across mediums or the fancier , a music venue that draws national names. The , 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 or get on stage at an open mic night at the .
Shopping
A bevy of boutiques makes Annapolis a great spot for guilt-free shopping (but there’s a big mall, too.)
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. 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, 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.
Johnnie Favorites
These spots are time-tested hangouts for students of St. John’s. See why.
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. 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 , 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.
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