Annapolis: Places to See, Things to Do

A Daytrip or Long Weekend

Less than an hour from Bethesda, Annapolis presents an exciting opportunity for a road trip, especially in the holiday season. A historically and culturally significant town, Annapolis wears many hats in both the past and present–our nation’s first capitol following the Revolutionary war, today it’s Maryland’s state capitol, as well as a college town, a sailing mecca, and a major tourist destination and foodie town.

  Despite its many roles, the waterfront town retains the charm of its local character. Nestled on the Annapolis Harbor at the mouth of the Severn River, the local character can be enjoyed as a change-of-pace daytrip, a weekend of adventure, or a romantic getaway. At just the right distance for a spontaneous getaway you head to Annapolis to get away from crowds or to find one. Whatever your goal, here is a brief list of events and places to help you find a bit of unforgettable fun in Annapolis.

An Officer and a Midshipman: The USNA

Annapolis: Places to See, Things to Do

Place to see: The Naval Academy

Annapolis is home to two very unique institutions of higher learning: the United States Naval Academy and St. John’s College (more on the second later).  The storied Naval Academy has been producing the future leaders of America’s navy since its founding in 1845.  Sometimes simply referred to as “Annapolis,” the Naval Academy is arguably as well known as its Army counterpart to the North. The campus of the Naval Academy, however, possesses its own unique grandeur–all it takes is a glimpse of the stately Bancroft Hall to see why the Naval Academy attracts droves of tourists each year. A daytrip to Annapolis should certainly include a tour of the Yard, and while there you should also stop into the USNA Museum and take in the long history of American naval leaders along with the Naval Academy’s role in shaping them.

A Light at Sea: The Light Parade

Annapolis: Places to See, Things to Do

Thing to do: Annual Eastport Yacht Club Light Parade

Light displays are a staple of the holiday season— let’s face it flashing lights and glowing snowmen in tableau are the look of the season. Nonetheless, even with lights everywhere the annual light parade of Annapolis stands out. Ask anyone, and they will tell you that a major highlight of the holidays in Annapolis is the light parade. Annapolis never lives up to its nome-de-plume as sailing capital of the world more than when the fleets of glowing boats sail up and down Annapolis Harbor. Always a fun and festive experience, this event is one the whole family can get behind, and which brings out a mix of tourists and locals to enjoys the sights. Dress warmly, though, it’s December and the winds on the harbor are chilly and brisk!

Dock of the Bay: City Dock

Annapolis: Places to See, Things to Do

Place to See: The Annapolis City Dock

To walk from Main Street to the City Dock is take a route dating back to the Revolutionary War. Today, there’s a lot more to do in this area than walk in the footsteps of George Washington. The City Dock is vibrant heart of town, where you’ll find many of Annapolis’s biggest events along with bars, restaurants, and boutiques for shopping. Once you’ve eaten your fill and shopped, there are still more things to do in the City Dock.  Ego Alley is a place to find seafarers in all sizes of pleasure boat enjoying the waves. In warmer months it’s the perfect location for people or boat watching.


A Shot for the Cup: The Annapolis Cup

Annapolis: Places to See, Things to Do

Thing to do: Annapolis Cup Croquet Match

Earlier we mentioned the second institution of higher learning that calls Annapolis home, St John’s College. Though occupying just 36 acres, next door to the Naval Academy, St. John’s is hardly in the shadow of the larger institution. A private college with a quirky all-primary source curriculum enrolls around 500 students, St. John’s was actually founded a few years before Yale, making it the third oldest college in the country. Each spring St. John’s students meet the Naval Academy midshipmen in a croquet match for the Annapolis Cup. St. John’s has only lost 7 times in the match’s 34 year history, and over time the congenial picnicking and lawn game has grown into a ticketed event attracting thousands. Still each year the Annapolis Cup is as much about the crowd as the match. In keeping with event tradition, jazz-age inspired looks intermingle with naval dinner dress.

. . .And there’s Chocolate: Chocolate Binge Festival

Annapolis: Places to See, Things to Do

Thing to do: The Chocolate Binge Festival

As if the previous places and events were not enough to merit a visit to Annapolis, there is also chocolate. . .lots of chocolate. This event serves several purposes, first it supports the Annapolis Arts Districts and the local Annapolis nonprofit We Care and Friends. Secondly, the festival marks the lighting of the West Street Light Canopy, which will light this area of Annapolis through the holiday season. Third purpose is, of course, chocolate. Just over two dozen local chocolatiers and vendors participate along with local artisans for a day of family oriented fun that includes a fire-pit for marshmallow roasting and other activities.  If you’ve got family coming into town and looking to keep several generations entertained—chocolate is hard to beat.

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