The 5 Best Day Trips From Washington, DC

Annapolis, the capital of Maryland, is chock-full of prestigious historic sites
Annapolis, the capital of Maryland, is chock-full of prestigious historic sites | © Mira / Alamy Stock Photo
Chloe Byrne

Washington, DC is the pulsing hub of the federal government, what with emblematic landmarks such as the White House and Supreme Court taking center stage. Named after America’s first president and founding father, the capital city has a current of political and historical energy flowing throughout its streets that draws over 20 million visitors annually. If you’re looking to escape the crowds for the day, you can easily do so with the seaside and sun-dappled wine country located just a matter of hours away by car.

Annapolis

Jutting out into the mouth of the Severn River, Annapolis has a rich maritime history. Its thriving shipping industry attracted many wealthy merchants who lay down roots with grand mansions – and many of these 18th-century structures still stand today. The Maryland capital is peppered with prestigious sites, including the red-brick Maryland State House, Romanesque St Anne’s Church and Beaux-Arts Naval Academy that sits on the waterfront.

1. Original Annapolis Seafood Crawl

Tours, Activities

Home of the oyster-roasting and sock-burning traditions – where locals celebrate the spring equinox with a feast of oysters (and by burning their worn winter socks) – Annapolis is the perfect place to tuck into the renowned seafood of Chesapeake Bay. On this tour, you’ll be whisked round the city on an e-cruiser, learning about its absorbing history and sibling rivalry with the community of Eastport. You’ll also stop at a number of local restaurants along your journey, giving you the chance to sample seasonal seafood such as oysters, clams, mussels and crabs – all locally caught.

Baltimore

Chesapeake region

In fictional terms, the Chesapeake region has a less than savory reputation – being the setting of the famous Hannibal book, film and TV series. In reality, however, the coastal region is better known for its mix of busy ports, dense forests and native wildlife and flora. Most notable among these are the blue crabs and oysters that have transformed it into a hub of the seafood industry.

3. Chesapeake Region Wine Tour

Tours, Activities

Quench your thirst and curiosity on this wine-fueled exploration of Maryland’s Eastern Shore. Taking you around the best wineries that Chesapeake has to offer, the tour delves into the inner workings of vineyards and introduces you to the local vintners who run them. As you learn about the craft of winemaking, you’ll also get the chance to sample some of the reds and whites. Upgrade to include a cheese plate or charcuterie board to enhance the taste even more (and soak up some of the vino).

Frederick

The striking skyline of Frederick looks like the zig-zag of a heart monitor, set with the pointed spires of its historic churches. The city is filled with fragments of its Civil War past – immortalizing the conflict with sites such as the Monocacy National Battlefield and National Museum of Civil War Medicine. Go for a rummage in the old-world treasure trove of the city’s 200 antique stores to find grand mementos, including grandfather clocks and authentic armoires.

4. Walking Tour of Frederick – the Crossroads of Maryland

Tours, Activities

History buffs will be entirely in their element as they follow historian guide Don through a city awash with evidence of its battle-worn past. The semi-professional photographer will demonstrate his passion for the subject as he leads you, rain or shine, round Frederick’s most historic sites. Stops include an Evangelical Lutheran church, the bucolic stretch of Carroll Creek Park and colonial City Hall – a storied structure with a collection of legend-has-it mysteries to delve into. As the rich heritage of the city is chronicled in engaging detail, you’ll learn of its transformation from German settlement to revitalized city.

Mount Vernon

Named after the sprawling estate of George Washington, Mount Vernon is one of Baltimore’s oldest neighborhoods and a designated National Historic Landmark District. Its towering centerpiece is the original Washington Monument, set among manicured Beaux Arts parks lined with stately homes. The area offsets an affluent suburban culture with historical institutions such as the Neo-Renaissance Peabody Library and a vibrant LGTBQ nightlife scene.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.

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