top of page
  • Writer's pictureLisa

Eat, Shop, Stroll, and be Nautical: Annapolis

Maryland's state capital disguised as a quaint harbor town and perfect day trip from DC.

As people dwelling in the capital of the the greatest nation in the world, Washingtonians sometimes have a tendency to live in a bubble. This bubble could apply to many things (People don't talk about politics everywhere? Your sister has never tried Ethiopian food? That town your friend's wedding is in doesn't even have Ubers?) but one thing we tend to forget about are the excellent capital cities within driving distance: Richmond and Annapolis.

This post is about Annapolis, just a 40-minute drive from DC. I've spent a lot of time in Annapolis over the years, between a college internship, spring and summer day trips with family, and even my bachelorette party. Here are just a few of the things to try in Maryland's capital on a nice spring or summer day.

Where: Annapolis, MD

Get there: ~40-minute drive from DC

Do: Cruise on the Bay, see a musical at the Annapolis Summer Garden Theatre, visit the state house, stroll and shop around town, visit the Amish Market, tour the U.S. Naval Academy

Eat/drink: Ice cream at Kilwins or Annapolis Ice Cream Company, stuffed baked potato at Potato Valley Cafe, Cafe Normandie or Iron Rooster for brunch, Federal House for dinner, Dock Street Bar and Grill or O'Brien's for casual drinks


Take a cruise around the harbor (with some drinks!) with Watermark Cruises' Queen Anne.

See a great community theater musical at an even greater price with the Annapolis Summer Garden Theatre. The theater is outdoors and it's a very cool experience. Even last year when we went and it started to rain, they brought the cast and audience together inside for an impromptu, a capella finale--and it was awesome! We try to go to at least one show every summer now. Plus, you can bring in your ice cream from across the street!

Visit the Maryland State House and see if you can stroll around inside. Sometimes they have free concerts in the atrium. (You can also force a stranger to take a picture of you and your friends from across the street.)

Annapolis has a lot of local shops and boutiques that are fun to shop in as you roam the cobblestone streets.

Drive a few minutes outside downtown and you'll discover an awesome Amish Market, full of homemade food and open on Thursdays, Fridays, and Saturdays.

Tour the U.S. Naval Academy. They offer guided walking tours to the public.


Grab some ice cream from Annapolis Ice Cream Company or Kilwins.

If you are in Annapolis for a weekday lunch, definitely treat yourself to one of the stuffed baked potatoes at Potato Valley Cafe.

Dock Street Bar and Grill is a reliable, no-frills pub for American food and drinks.

Try Federal House for a slightly classier meal.

O'Brien's is good for seafood by day, drinks and dancing by night.

Annapolis is the closest you get to a summer getaway this side of the Bay Bridge--try leaving our capital for another one this year!

86 views0 comments

Recent Posts

See All


bottom of page