7 Highlights And 3 Letdowns Of Visiting Maryland

Maryland might not be the first state that pops into your head when planning a vacation, but trust me, this quirky mid-Atlantic gem has more personality than you’d expect. I’ve explored its charming harbor towns, wandered through historic battlefields, and yes, eaten enough crab cakes to qualify as a local. But like any destination, Maryland comes with its share of surprises; some delightful, others not so much. Here’s my honest take on what makes Maryland worth the trip and what might leave you scratching your head.

1. Highlight: The Inner Harbor is Pure Magic

Baltimore’s Inner Harbor feels like stepping into a postcard where history and modern energy collide in the best way possible. Walking along the waterfront, you’ll find street performers juggling fire, historic ships you can actually board, and the National Aquarium glowing like a giant blue jewel. The energy here is contagious.

Grab some Berger cookies from a nearby shop and watch the boats drift by while seagulls perform their chaotic aerial ballet overhead. The harbor transforms as the sun sets, with lights reflecting off the water creating this almost dreamlike atmosphere. Restaurants line the edge, offering everything from fresh seafood to international cuisine.

I spent an entire afternoon just wandering aimlessly, discovering hidden plaques about naval history and stumbling upon impromptu concerts. Whether you’re into maritime museums or just want to people-watch with an ice cream cone, the Inner Harbor delivers that perfect vacation vibe without trying too hard.

2. Highlight: Crab Feasts Are a Religious Experience

Nothing prepares you for your first proper Maryland crab feast. Picture this: newspaper-covered tables, mountains of steaming blue crabs dusted with Old Bay seasoning, and locals wielding mallets like seasoned warriors. It’s messy, it’s loud, and it’s absolutely glorious.

The ritual itself is part of the charm; cracking shells, digging for that sweet lump meat, and inevitably getting Old Bay under your fingernails for the next three days. Marylanders take their crabs seriously, and you’ll hear passionate debates about the best crab shacks with the intensity usually reserved for sports rivalries. I recommend hitting up a waterfront spot where you can crack crabs while watching the sunset.

Fair warning: this isn’t dainty dining. You’ll work hard for every bite, your hands will smell like the Chesapeake Bay, and you might question if it’s worth the effort. Then you taste that perfectly seasoned crabmeat, and suddenly you understand why Marylanders are so obsessed.

3. Highlight: Annapolis Oozes Colonial Charm

Annapolis feels like someone preserved a slice of 18th-century America and sprinkled in just enough modern coffee shops to keep things interesting. Cobblestone streets wind past colonial buildings that have stood since before the Revolutionary War, and the whole town smells faintly of salt air and history. The State House dome rises above it all, reminding you this was once the nation’s capital.

Wandering through the historic district, I kept stumbling upon plaques marking where famous founding fathers ate dinner or signed important documents. The Naval Academy adds this crisp, disciplined energy to the town, with midshipmen in uniform jogging past centuries-old taverns. Down by the harbor, sailboats bob in their slips while yacht club members sip cocktails.

What I loved most was how Annapolis manages to honor its past without feeling like a stuffy museum. You can tour a colonial mansion in the morning and grab craft beer at a waterfront brewery by afternoon.

4. Highlight: Ocean City Boardwalk Never Sleeps

Ocean City’s boardwalk is three miles of pure, unapologetic seaside chaos, and I mean that in the most affectionate way possible. Neon lights flash from arcade games, the smell of Thrasher’s fries and caramel corn fills the air, and somewhere in the distance, kids are screaming on roller coasters. It’s gloriously tacky and completely irresistible.

I challenge you to walk the entire boardwalk without buying at least four things you don’t need; airbrushed t-shirts, hermit crabs, saltwater taffy, maybe a questionable temporary tattoo. The beach stretches endlessly beside you, offering a calmer alternative when the boardwalk energy gets overwhelming. Summer nights here pulse with life as families, teenagers, and retirees all mingle in this democratic celebration of beach town fun.

Sure, it’s touristy and crowded, especially on weekends. But there’s something genuinely joyful about Ocean City’s refusal to be sophisticated. Sometimes you just need fried dough and skeeball, and this place delivers both spectacularly.

5. Highlight: Antietam Battlefield Tells Powerful Stories

Standing on the fields of Antietam, where America’s bloodiest single day of combat unfolded, hits differently than reading about it in textbooks. The landscape rolls gently, almost peacefully, marked by monuments and cannons that seem to whisper their stories. Over 23,000 soldiers were killed, wounded, or went missing here in just twelve hours.

Walking the Sunken Road; nicknamed Bloody Lane; I felt the weight of history pressing down. The park rangers give incredible tours, bringing those desperate September hours to life with details that make your chest tighten. You’ll see the Dunker Church, the Burnside Bridge, and fields where farmers still occasionally find bullets and buttons.

What makes Antietam special isn’t just the history lesson, though that’s profound. It’s the quiet reflection the landscape demands. Bring a picnic, sit beneath one of the old trees, and just absorb the significance of the ground beneath you. This place changed America forever, and you can feel that importance in your bones.

6. Highlight: Assateague Island Has Wild Ponies

Assateague Island is where Maryland gets wonderfully weird. Wild ponies roam freely across windswept beaches and salt marshes, descendants of horses that supposedly survived a Spanish shipwreck centuries ago. Watching these shaggy, tough little horses trot past your beach blanket feels surreal, like stumbling into a fantasy novel.

The island itself is pristine; untouched beaches stretching for miles, perfect for beachcombing and spotting dolphins offshore. I spent hours kayaking through the marshes, navigating narrow channels while herons watched judgmentally from the reeds. The ponies appear when they feel like it, completely unbothered by human admirers snapping photos. Park regulations prohibit touching them, which is wise since they’re wild animals despite their adorable appearance.

Camping here offers an experience you won’t find at typical beach resorts. Fall asleep to waves crashing and wake up to ponies wandering past your tent. Just remember to secure your food; these clever horses have mastered the art of cooler raids.

7. Highlight: Frederick’s Downtown is Underrated Gold

Frederick snuck up on me completely. I expected a sleepy small town and instead found this vibrant downtown packed with indie bookstores, craft breweries, and restaurants that could hold their own in much bigger cities. The historic district radiates charm without feeling manufactured, with Victorian buildings housing everything from vintage shops to innovative galleries.

Carroll Creek Park runs through downtown, transformed from a flood-prone stream into this gorgeous linear park with bridges, public art, and waterside cafes. I grabbed coffee and wandered for hours, discovering murals hidden in alleys and stumbling into a farmers market bursting with local produce. The food scene here genuinely impressed me; farm-to-table spots, authentic ethnic cuisine, and bakeries that made me reconsider my life choices.

What Frederick does brilliantly is balance preservation with progress. History buffs can explore Civil War sites and museums, while younger crowds flock to the breweries and live music venues. It’s the kind of town that makes you think about relocating before you’ve even finished your first visit.

8. Letdown: Traffic Around DC is Soul-Crushing

Let me be brutally honest: the traffic situation in Maryland’s DC suburbs will test your patience like few things can. The Beltway and I-270 transform into parking lots during rush hours that seem to last all day. What should be a twenty-minute drive somehow becomes an hour-and-a-half ordeal involving creative profanity and questioning your vacation choices.

Even Google Maps seems to give up, offering route alternatives that are all equally terrible. The constant construction projects promise future improvements while currently making everything worse. I’ve sat motionless on highways watching entire podcasts play out, my vacation time evaporating in exhaust fumes and frustration.

If you’re visiting Maryland and need to navigate the DC area, plan accordingly. Leave absurdly early for anything time-sensitive. Consider the Metro when possible, despite its own quirks. Or better yet, base yourself in Baltimore or Annapolis and avoid the DC suburbs entirely. Your blood pressure will thank you, and you’ll actually have time to enjoy Maryland’s better offerings instead of memorizing license plates.

9. Letdown: Weather is Ridiculously Unpredictable

Maryland’s weather has serious commitment issues. I’ve experienced all four seasons in a single day here, which sounds charming until you’re caught in a surprise thunderstorm wearing shorts and flip-flops. Spring and fall are particularly chaotic, swinging between gorgeous sunshine and torrential downpours with zero warning.

Summer brings this oppressive humidity that makes you feel like you’re breathing soup. The air gets so thick you can practically see it, and stepping outside feels like walking into a warm, wet blanket. Winters are equally confused; one week brings crippling snowstorms, the next offers weirdly pleasant sixty-degree afternoons. Packing for a Maryland trip becomes an exercise in bringing your entire wardrobe because who knows what you’ll actually need.

The Chesapeake Bay creates its own weather patterns, meaning forecasts are more like educated guesses. I learned to always carry layers, sunscreen, an umbrella, and a sense of humor. Maryland’s weather will keep you guessing, and not always in a fun adventure kind of way.

10. Letdown: Everything Closes Surprisingly Early

Outside of Baltimore and the tourist zones, Maryland rolls up its sidewalks shockingly early. I’ve wandered through charming small towns at eight o’clock on a Saturday night, desperate for dinner, only to find everything dark and locked. Apparently, many Maryland establishments operate on a schedule better suited to colonial times than modern tourism.

Even in decent-sized towns, restaurants stop seating by nine, shops close by six, and good luck finding anything open on Sundays beyond chain restaurants. This early-to-bed culture caught me off guard repeatedly. I’d finish a day of sightseeing around seven, ready to explore the local dining scene, only to discover my options were limited to gas station snacks or driving thirty minutes to find something open.

Beach towns are exceptions during summer, staying lively later into the evening. But venture inland, and you’ll need to adjust your expectations. Plan dinners earlier, stock up on snacks, and embrace Maryland’s apparently strong commitment to reasonable bedtimes. Night owls will find this aspect frustrating.