Home to tasty blue crab, the oldest state capitol building in continuous use, and the U.S. Naval Academy, Annapolis is rich in history and cultivating a blossoming food scene. It wasn’t until my daughter accepted her appointment to the academy in 2018 that we started making frequent visits to this quaint harbor town. With every trip, we discover something new and unexpected, like Old Fox Books & Coffeehouse, more like the home library of your dreams than a store (pictured below).
Main Street activities start at Church Circle and make their way down to City Dock, where boats of all sizes come to park and the passengers hop off to grab a meal and catch up with their “mids” (midshipmen is the term used to describe students at the academy). Here you will find some staple chains (Starbucks, Dunkin Donuts, Chipolte, CVS) mixed in among the tourist traps and boutiques offering their local wares. You will find some of my favorites around the newly reopened Market House-a collection of indoor eateries offering healthy and seasonal fare.
Up for something a little sweet instead? A few hundred feet away you will find Sofi’s Crepes, cooking up sweet filled thin pastries or more savory cheesy goodness handed to you hot, in a tin foil sleeve. We never miss the chance to fuel up here, especially when it’s chilly out.
Set aside a half a day to tour the academy. The visitor’s center is impressive and it can easily take an hour or two to get your introduction to this impressive establishment. Sign up for the docent led tour that takes you through the different buildings, from Bancroft, the world’s largest dormitory, to the chapel, whose basement holds the remains of John Paul Jones in one of the most ornate caskets I’ve ever laid eyes on. At every turn, the staff is extremely knowledgeable and if you’re really a nautical history buff, pencil in a few more hours for the Annapolis Navy Museum at Preble Hall. If you happen to visit between Monday and Friday, treat yourself to lunch between 11 and 2 at the Alley, an otherwise members only eating establishment on campus.
“I wish to have no connection with any ship that does not sail fast; for I intend to go in harm’s way.”
John Paul Jones, Naval Commander
Depending on the length of your stay in Annapolis, you can check out the capitol building, take in a live show at Ramshead Tavern, or hop the water taxi to the other side of the bay to watch the sunset while dining waterfront. There are plenty of fine dining options and a handful are seafood focused serving regional specialties.
Or, venture further out of town in search of the true crack and eat blue crab experience like the one at Cantler’s Riverside Inn, where the wooden tables provide family style seating and the guests wear bibs while they gobble up seafood and corn as soon as it’s thrown down. Head downstairs to the dock to watch today’s catch come in and get sorted while taking in the view. Need a spot for a late night drink…it’s S.O.B. (Sailor’s Oyster Bar), a very small, cozy space with a fantastic selection of top shelf libations, as well as an offering of fresh oysters on the half shell and tinned fish plates that I can’t seem to replicate here on the west coast. They make an old fashioned just the way I like it, Bulleit Rye, orange peel and a maraschino cherry.
Stay- Graduate Annapolis or Hilton Garden Inn
Eat- Breakfast at The Iron Rooster, lunch at Sailor Oyster Bar, and for dinner, take the water taxi from city dock to The Chart House (ask for a table at the window for the view) or Lewnes’ Steak House
MAKE THE TRIPS 
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