Maryland may be small in size, but it packs a punch when it comes to history, culture, and natural beauty. From the bustling waterfront of Baltimore to the serene shores of the Chesapeake Bay and the rugged mountains of Western Maryland, the state offers a little bit of everything. Whether you’re drawn to its rich colonial past, its vibrant food scene (hello, crab cakes!), or its outdoor adventures, Maryland’s diverse regions make it a destination worth exploring.
Regions
The state is characterized by a variety of landscapes, including mountains, beaches, forests, and urban areas. While they have spent a lot of time in Maryland, neither the Family nor the Dinks have visited all 5 regions. The one region neither have visited is The Western Region.
- Central Maryland: Home to Baltimore, Maryland’s largest city, this region blends historic charm, cultural landmarks, and vibrant neighborhoods, from the Inner Harbor to Fell’s Point.
- Capital Region: Encompassing areas like Annapolis and the Maryland suburbs of Washington, D.C., this region offers a unique mix of political history, waterfront beauty, and easy access to the nation’s capital.
- Western Maryland: Known for its rugged mountains, scenic state parks, and historic towns like Cumberland and Hagerstown, this region is a haven for outdoor enthusiasts and history buffs alike.
- Southern Maryland: With its peaceful waterfronts along the Chesapeake Bay and deep colonial history, Southern Maryland offers charming small towns, fresh seafood, and important historical sites like St. Mary’s City.
- Eastern Shore: A paradise for nature lovers, the Eastern Shore boasts scenic beaches, quaint coastal towns like St. Michaels, and iconic destinations like Ocean City — perfect for a relaxing getaway.
The Same
Both the DINKs and the family have plenty of ties to the Northern Virginia area, which has made Maryland a frequent destination over the years. From regular trips to Baltimore’s Inner Harbor and the beaches along the Eastern Shore to exploring charming small towns, historic sites, and scenic parks, Maryland has become a familiar and favorite place to visit. Each trip offers something new, whether it’s indulging in iconic crab feasts, taking in a baseball game at Camden Yards, or venturing into the rolling hills and mountain trails.
The Baltimore Metro:
Baltimore has become a frequent stop for both the family and the DINKs, thanks to its convenient location and vibrant personality. Whether it’s work trips, quick getaways, or visits to family in nearby Northern Virginia, there always seems to be a reason to spend time in Charm City. From its historic waterfront and world-class museums to its lively neighborhoods and incredible seafood, Baltimore offers something for everyone — making it a city we’re always happy to return to.
Check out The Dinks and the Family’s contrasting experiences in our blog below.
Ocean City:
Ocean City, Maryland, is a beloved coastal resort town located along the Atlantic Ocean. Known for its pristine beaches, lively boardwalk, and array of attractions, Ocean City offers a classic beach vacation experience for visitors of all ages. We visited it together so there is a lot of similarities. Check out our blog below to learn more.
The DINKs
We had the chance to visit a cousin who lived in Annapolis, giving us a perfect excuse to explore this beautiful and historic city. We loved strolling through the charming streets, admiring the colonial architecture, and soaking in the waterfront views at Annapolis Harbor. Of course, no visit was complete without stopping for lunch at a local brewery, where we enjoyed good food, great beer, and the laid-back coastal vibe that makes Annapolis so special.
Annapolis
- Maryland State House: The State House in Annapolis is the oldest state capitol still in continuous legislative use, and it served as the temporary United States Capitol from 1783 to 1784.
- United States Naval Academy: The Naval Academy, established in 1845, is a prestigious institution located in Annapolis. Visitors can explore the campus and attend events such as the Blue Angels air show during Commissioning Week.
- City Dock: Annapolis’ waterfront City Dock area is a bustling hub of activity, offering boat tours, waterfront dining, and scenic views of the Chesapeake Bay.
The Family
We often stay at Hyatt hotels as they are the best value for hotel points. We found the Hyatt Regency Chesapeake Bay and truly enjoyed this family-friendly hotel overlooking the bay, especially over Independence Day weekend.
The Chesapeake Bay:
There’s nothing quite like watching fireworks light up the sky over the serene waters of the Choptank River, and the Hyatt Regency Chesapeake Bay offers a front-row seat to the show. Whether you’re sitting out on the resort’s expansive lawn, relaxing by the fire pit, or even floating in the pool, the reflections of the colorful bursts dancing on the water create a magical, picture-perfect moment. Pair it with a local craft beer or a classic Maryland crab feast, and you’ve got an unforgettable Eastern Shore experience.
Summary
From the serene shores of the Chesapeake Bay to the bustling streets of Baltimore and the scenic trails of the Appalachian foothills, Maryland offers a little bit of everything. Its rich history, vibrant cities, charming small towns, and stunning natural beauty make it a destination both the Family and the DINKs have returned to time and again. Whether it’s savoring fresh seafood, strolling historic harbors, relaxing on sandy beaches, or discovering hidden gems in the countryside, every visit has offered something new to explore. With so much variety packed into a relatively small state, Maryland continues to surprise and delight—making it a favorite stop along the East Coast and a place we’ll no doubt keep coming back to.
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