Best Places to Visit in Maryland
Maryland is a state that blends coastal charm, rich history, and natural beauty, offering something for every type of traveler. From lively waterfront cities and historic landmarks to peaceful mountain escapes, Maryland is full of destinations worth exploring.
I’ve strolled along bustling harbors, explored charming small towns, and discovered scenic trails that showcase the state’s diverse landscapes. Whether you’re planning a family trip, a romantic getaway, or a weekend adventure, Maryland offers plenty of things to do and places to visit. Here are the ones I recommend, and I think you’ll enjoy them too.
1. Nautical Nostalgia in Annapolis
I drove one hour northeast from Washington, D.C. into Annapolis, Maryland’s capital and a seaport with colonial roots.
When I first arrived in Annapolis, I instantly felt the magic of this vibrant harbor town, located right on the Chesapeake Bay near Baltimore and Washington, D.C.
Walking through the cobblestone streets lined with colonial buildings was one of the most exciting experiences, and I loved how every corner felt like discovering a hidden gem from America’s past.
My absolute favorite spot was the U.S. Naval Academy—this historic and spectacular campus was filled with monuments, gardens, and museums that truly captured the spirit of Annapolis.
I found myself relaxing by the waterfront, watching sailboats glide across the bay, and it was the best kind of weekend getaway vibe—romantic yet also perfect for a family adventure.
Some of the coolest moments came from exploring the boutique shops and unique restaurants along Main Street, where I enjoyed fresh seafood and unforgettable Maryland crab cakes.
I thought the State House was especially interesting, as it’s the oldest U.S. state capitol still in use, and standing inside made me feel part of something extraordinary.
One of the most underrated experiences was simply wandering near Ego Alley, where boats pulled up right by the dockside cafés—it felt joyful and lively, like a little festival every evening.
Whether I was sipping coffee at a cozy café, taking a romantic sunset cruise, or admiring the historic charm, Annapolis gave me the coolest mix of history, beauty, and fun.
For me, it’s one of the best destinations in Maryland and an unforgettable place to visit again and again.
Later, at HERE, I browsed tables of locally made jewelry, ceramics, and linen goods. The space was bright and full of life, with artists chatting beside their work and the scent of lavender soap and fresh coffee in the air. I left with a hand-poured candle and the feeling that I’d seen two sides of Annapolis in the same afternoon, its roots, and its spark.
2. Baltimore: Harbor Charm & Crab House Comfort
I drove 50 minutes northeast from Washington, D.C. into Baltimore, Maryland’s largest city and a historic port on the Patapsco River.
When I visited Baltimore, I realized right away this city is one of Maryland’s absolute best destinations, sitting right on the beautiful Chesapeake Bay and near the Atlantic coast—it’s a place where water, history, and culture all meet on the costa.
One of my favorite experiences was exploring the Inner Harbor, which felt like the vibrant heart of the city, filled with cool attractions, restaurants, and the most spectacular waterfront views right on the costa.
I loved visiting the National Aquarium, an amazing and underrated gem where I found myself face-to-face with sharks, tropical fish, and even playful dolphins—it was one of the most joyful parts of my trip.
Walking around Fell’s Point was another highlight for me; this historic neighborhood had cobblestone streets, lively pubs, and the kind of old-world charm you don’t often find right here on the East Coast costa.
I thought the American Visionary Art Museum was truly unique, showcasing unusual and creative works that made Baltimore feel like the coolest art city right on the costa.
Savoring a plate of iconic Maryland blue crabs was the best foodie experience, and enjoying them with Old Bay seasoning right on the waterfront felt like a dream come true.
I also loved how Camden Yards offered such an exciting baseball experience—it’s one of the most beautiful stadiums in the country and sits so close to all the action downtown.
For me, Baltimore is a brilliant idea for a weekend getaway—romantic, family-friendly, and filled with some of the most exceptional experiences you’ll find anywhere along the costa.
3. Trailheads and Quiet Streets in Hagerstown
From Harpers Ferry, West Virginia, it was a 40-minute drive north into Hagerstown, where the Blue Ridge meets the Cumberland Valley.
When I made my way to Hagerstown, Maryland, I found it to be one of the most underrated gems in the state, tucked away in the scenic Washington County near the Appalachian Mountains and the West Virginia border.
I loved exploring the vibrant Hagerstown City Park, which felt like the absolute best spot for a joyful afternoon with its lake, walking trails, and the amazing Washington County Museum of Fine Arts right here on the grounds.
One of my favorite experiences was wandering through the Hagerstown Cultural Trail, a cool and creative walkway that connects the downtown district to the park while showing off unique public art installations.
I thought the Maryland Theatre downtown was such a spectacular place to catch a performance, and it gave me the exciting feeling of being part of the city’s thriving arts scene right here in Hagerstown.
For history lovers like me, the proximity to Antietam National Battlefield was a dream—it’s just a short drive and offered one of the most meaningful and interesting experiences in the entire region.
I also enjoyed discovering the local restaurants and breweries downtown, which gave me that hidden gem feeling of a cool foodie getaway without big city crowds.
The Premium Outlets here were another favorite stop—shopping with mountain views in the background made it feel like a unique twist on retail therapy.
For me, Hagerstown is one of the best small-city destinations in Maryland, combining history, culture, and natural beauty into an unforgettable getaway right here in the heart of the state.
4. Forest Trails and Covered Bridges in Thurmont
From Gettysburg, Pennsylvania, it was a 30-minute drive south into Thurmont, where rolling farmland meets forested ridges.
Tucked away in the foothills of the Catoctin Mountains, Thurmont, Maryland quickly won me over as one of the state’s most spectacular hidden gems, right here in Frederick County near the Pennsylvania border.
My favorite experience was exploring Cunningham Falls State Park, where I hiked to the tallest cascading waterfall in Maryland—it felt like stepping into a hidden dream right here in Thurmont.
I thought Catoctin Mountain Park was one of the coolest spots, with endless trails, overlooks, and that unusual thrill of being so close to Camp David, a place filled with history and mystery.
Wandering downtown Thurmont gave me the joyful charm of a classic small town, with local shops, murals, and cozy cafés that made the experience feel truly unique and underrated.
I absolutely loved attending the Catoctin Colorfest in the fall—it was an amazing explosion of art, crafts, food, and music, and it turned Thurmont into the most vibrant festival scene right here in the mountains.
One of the best hidden gems was Roddy Road Covered Bridge, a romantic and picturesque spot that felt like walking into a storybook setting.
Nearby, I found cool wineries and orchards where I could sip cider, taste local wines, and enjoy the peaceful countryside views—it was the perfect family or couples’ getaway idea.
For me, Thurmont is one of the most spectacular small towns in Maryland, offering a mix of natural beauty, historic charm, and unforgettable experiences right here in the Catoctin Mountains.
5. Berlin
From Salisbury, it was a 35-minute drive east into Berlin, where restored 19th-century buildings now house boutiques and cafés.
Nestled on Maryland’s Eastern Shore, just a few miles from Ocean City, Berlin is one of the coolest and most underrated small towns I’ve ever explored right here on the Atlantic coast.
My favorite experience was strolling through the historic downtown, where every building looked like it belonged in a storybook—colorful storefronts, quirky boutiques, and charming cafés gave the whole place an amazing and vibrant energy.
I thought the Atlantic Hotel was one of the best hidden gems; this historic inn felt like stepping back in time, and it added so much character to the town’s main street.
Exploring the local art galleries and antique shops was one of the most joyful parts of my visit—I loved how each spot felt unique, with treasures waiting to be discovered right here in Berlin.
What made the trip even more exciting was how close the town is to Assateague Island; within minutes, I was surrounded by wild ponies and spectacular coastal views that felt like a dream getaway.
Berlin also had the coolest food scene, from fresh seafood restaurants to hidden cafés serving homemade pies—it was an absolute best foodie surprise in such a small town.
Seasonal festivals like the Berlin Bathtub Races and Fiddler’s Convention turned the streets into one big celebration, and I couldn’t help but feel the joyful community spirit everywhere I went.
For me, Berlin is one of Maryland’s most exceptional small-town destinations, offering history, fun, and unforgettable coastal experiences right here on the shore.
6. Bay Breezes in St. Michaels
I caught the Oxford–Bellevue Ferry (about 20 minutes, $5) across the Tred Avon River, then a short drive into St. Michaels. With only about 1,000 residents, the town is small but buzzing in summer.
Right on the Chesapeake Bay’s edge, St. Michaels is one of the most spectacular small towns in Maryland, and I found it to be the perfect mix of coastal charm and historic elegance right here on the Eastern Shore.
My favorite experience was walking along the waterfront, where sailboats drifted by and the views made every moment feel like a dream getaway.
I thought the Chesapeake Bay Maritime Museum was the absolute best attraction, filled with fascinating exhibits, boats, and even a historic lighthouse that gave me such a unique and interesting glimpse into the bay’s past.
Downtown St. Michaels quickly became one of my favorite spots, with its boutique shops, hidden art galleries, and cozy cafés that gave the whole town a joyful and vibrant energy.
Savoring fresh crab cakes and oysters at a local dockside restaurant was an amazing foodie highlight—it felt like the coolest way to experience authentic Maryland flavors right here on the water.
I also loved how St. Michaels offered such a romantic vibe, with charming inns and bed-and-breakfasts that made the town perfect for a weekend escape.
Exploring by bike was another brilliant idea—riding through scenic backroads and past historic homes made me feel like I was uncovering hidden gems at every turn.
For me, St. Michaels is one of Maryland’s best coastal treasures, offering history, dining, and unforgettable waterfront experiences all in one magical place right here on the bay.
7. Quiet Roads and Barns in Waldorf
I caught a commuter bus from Washington, D.C. (about 50 minutes, $7). With more than 80,000 residents, Waldorf blends suburban bustle with access to Southern Maryland.
Located in Southern Maryland, just a short drive from Washington, D.C., Waldorf is one of those underrated towns that surprised me with its mix of history, shopping, and family-friendly fun right here in Charles County.
One of my favorite experiences was visiting Dr. Samuel Mudd’s House & Museum, a hidden gem filled with fascinating Civil War history and stories connected to President Lincoln—it was one of the most interesting places I’ve seen right here in Maryland.
I thought the local parks were some of the coolest features of Waldorf; places like Cedarville State Forest gave me peaceful trails, camping areas, and an awesome chance to escape into nature without traveling far.
For a more vibrant vibe, St. Charles Towne Center was the absolute best shopping destination, with plenty of stores, dining spots, and entertainment that made for a joyful afternoon getaway.
I also loved exploring the Indian Head Rail Trail nearby, a unique and exciting path perfect for biking or walking while taking in the scenic countryside views.
Savoring local seafood and discovering hidden restaurants around town was another highlight—Waldorf had some amazing spots that felt like true local favorites.
What stood out to me most was how affordable and family-friendly Waldorf felt—it was easy to plan a weekend filled with history, outdoor adventure, and cool small-town experiences right here close to the capital.
For me, Waldorf is one of the best underrated destinations in Maryland, offering history, shopping, and outdoor fun all in one place.
8. River Light and Small-Town Rhythm in Havre de Grace
We drove 1 hour northeast from Baltimore to Havre de Grace, a waterfront town where the Susquehanna River meets the Chesapeake Bay.
Perched right where the Susquehanna River meets the Chesapeake Bay, Havre de Grace is one of Maryland’s most spectacular waterfront towns, and I loved how it blended small-town charm with incredible coastal views right here in Harford County.
My favorite experience was walking the Havre de Grace Promenade, a scenic boardwalk that stretched along the water and gave me the most joyful views of sailboats, birds, and sparkling sunsets.
I thought the Concord Point Lighthouse was one of the coolest hidden gems—it’s the oldest publicly accessible lighthouse in Maryland, and standing there felt like stepping back into maritime history right here on the bay.
Downtown Havre de Grace quickly became one of my favorite spots, with unique shops, antique stores, and cozy cafés that made the whole area feel vibrant and welcoming.
Visiting the Decoy Museum was an unusual but fascinating highlight—I never knew waterfowl hunting culture had such an amazing history, and the handcrafted decoys were truly works of art.
Savoring fresh seafood at a dockside restaurant gave me the absolute best Chesapeake Bay flavors, and it made the experience feel like a perfect coastal getaway.
I also loved discovering the Susquehanna State Park nearby, with its trails, historic sites, and beautiful river views—it was an exciting and affordable way to enjoy nature right here in the region.
For me, Havre de Grace is one of Maryland’s coolest and most underrated towns, offering history, scenery, and unforgettable waterfront experiences all in one magical destination.
9. Mountain Echoes in Cumberland
I drove 1 hour 15 minutes west from Hagerstown into Cumberland, a historic canal and railroad city tucked in the Allegheny Mountains.
Nestled in the mountains of Western Maryland, Cumberland is one of the most spectacular hidden gems I’ve explored, offering history, nature, and small-city charm all right here near the West Virginia border.
My favorite experience was walking through the historic downtown, where brick-lined streets, vibrant murals, and unique shops created a joyful and welcoming vibe that felt both cool and underrated.
I thought the Western Maryland Scenic Railroad was the absolute best attraction—it took me on a nostalgic train ride through the mountains, and the views were nothing short of spectacular.
Visiting Canal Place gave me such an interesting look into history, with the C&O Canal and heritage museums telling the story of how Cumberland once thrived as a transportation hub right here in the Appalachians.
For outdoor adventures, I loved the Great Allegheny Passage trail, which started in Cumberland and stretched all the way to Pittsburgh—it was a dream spot for biking, hiking, and soaking up mountain scenery.
Exploring the arts scene was another favorite part of my trip; galleries and live music venues gave the city an exciting and vibrant edge that I didn’t expect in a small mountain town.
One of the coolest hidden spots nearby was Rocky Gap State Park, where I enjoyed hiking, swimming, and even checking out the lakeside resort—it felt like a full getaway within minutes of downtown.
For me, Cumberland is one of Maryland’s best underrated destinations, offering history, culture, and unforgettable mountain experiences right here in the heart of the Appalachians.
10. Storybook Streets in Ellicott City
From Washington, D.C., it was a 50-minute drive north into Ellicott City.
Set along the Patapsco River just west of Baltimore, Ellicott City is one of the most spectacular and historic towns in Maryland, and I was completely charmed by its vibrant mix of history, shopping, and natural beauty right here in Howard County.
My favorite experience was strolling down Historic Main Street, where I found cool antique shops, cozy cafés, and unique boutiques all tucked into 18th- and 19th-century stone buildings—it felt like stepping into a hidden gem from another era.
I thought the B&O Railroad Museum was one of the most interesting attractions; learning about America’s first railroad line right here in Ellicott City gave me an unusual and exciting perspective on history.
For a joyful outdoor adventure, I loved exploring Patapsco Valley State Park just minutes away, where I hiked scenic trails, crossed swinging bridges, and enjoyed some of the coolest river views in the region.
One of the absolute best discoveries was the town’s thriving art scene—murals, galleries, and live music venues added so much vibrant energy to the historic setting.
I also enjoyed uncovering the town’s unique ghost tours, which gave me a fun and unusual way to experience Ellicott City’s rich (and sometimes spooky) past.
Dining here was another highlight, with everything from local breweries to romantic restaurants offering the perfect mix of flavors—it felt like a brilliant idea for both a weekend getaway and a family trip.
For me, Ellicott City is one of Maryland’s coolest and most underrated destinations, offering history, culture, and spectacular riverfront charm all in one unforgettable place.
Conclusion
Exploring Maryland has shown me just how many amazing and underrated places are tucked into this spectacular state.
Each destination gave me joyful, exciting, and unforgettable experiences—whether it was a romantic getaway, a family trip, or just a weekend escape.
For me, the absolute best part of traveling through Maryland is discovering how much variety, beauty, and vibrant culture exists right here so close together.
No matter where you go in this state, there’s always something cool, unusual, and special waiting to be explored.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
