Off to Annapolis

Annapolis is one of my favorite East Coast cities. It’s charming and quaint, and it also happens to be the city where MBH and I first met. We travel up most years for the annual croquet match of the Academy vs. St. John’s College, which has become the kind of citywide celebration & boozefest I can get behind.

A few weekends ago, we took the family up for a long Annapolis weekend, driving up on a Friday so our son could nap in the car and we’d still have time to explore the city with friends. We stayed a bit further from downtown (DTA for those in the know) than we normally do, and I wouldn’t recommend it. We missed being out of the city center, parking became a factor in decisions, and it cut down on the ease and accessibility of exploring a city we love.

We spent the day exploring the Academy, which, since it’s also a national park, is one of the most gorgeous colleges in the U.S. We spent the evening revisiting some well-loved favorites.

With our son passed out for a late nap in his stroller, we stopped at Middleton Tavern for a round of cocktails and a plate of oysters we didn’t have to share.

Saturday was spent reconnecting with old friends in the city.

On Sunday before we headed out of town we decided to stop once more for brunch at Rams Head. To our surprise, the streets were blocked off. We parked a little further away, broke out the stroller, and strolled down a brick lane to see what all the fuss was about, and discovered First Sunday Arts Festival, which happens (take a guess…) every first Sunday in town.


It was gorgeous. Most restaurants, including Rams Head, added extra seating outdoors, cafe-style, to take advantage of the foot traffic and the perfect weather. We eagerly snapped up a table, only to realize that it meant our son had walking access to every booth within our line of sight. Once he realized he could get away, and explore, there was no stopping him.

He found a set of stairs nearby and insisted on climbing them – over and over and over again, while MBH and I traded off on sitting down and eating brunch with chasing him around the market square.

After a really excellent crab cake brunch (because what else would you honestly get in Maryland) we moseyed through the booths and back to our car, and trekked the long way home, stopping partway so our son could get out and stretch his toddler legs beyond enjoying the spectacular view of the Chesapeake Bay the whole way home.


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