Maryland With Kids Family Travel Guide

🦀Maryland Wild horses on the beach at Assateague Island

The horses on the Maryland end of Assateague walk out of the dunes and across the road like they own it, which they more or less do. You watch from the car and you do not feed them.

State Guide

Maryland With Kids Family Travel Guide

“Maryland is the whole country in two and a half hours of driving. Mountains at one end, ocean at the other, crabs in the middle.”

Why families hire me for Maryland

Maryland gets written up as a day trip from Washington. It is a full week, and the reason nobody tells you that is that nobody looks at the map properly.

I have planned and priced more than three hundred trips and Maryland is one of the states I end up recommending to families who did not ask about it. They come to me wanting a week with a beach, some history the kids will actually absorb, and drives that do not ruin everyone. That is this state almost exactly.

It is about two and a half hours from the Appalachian mountains in the west to the Atlantic in the east. In between you get Baltimore, the Chesapeake Bay, a working waterman culture, two national battlefields, a canal you can bike for a hundred and eighty miles, and a barrier island with wild horses on it.

The thing that sells it to kids is the Bay. Blue crabs on brown paper with a mallet, boats everywhere, fossil shark teeth you can actually find on the beach at Calvert Cliffs, and a boardwalk at Ocean City that has not changed much in fifty years.

I taught social studies for eight years and Maryland is unusually rich for it. Fort McHenry is where the national anthem was written, and standing there with the flag up makes the story stick. Antietam is the bloodiest single day in American history and it is quiet and unspoiled and it does the work without anybody raising their voice. The Harriet Tubman byway runs through the country she was born in and escaped from.

What I do is the part that is hard from outside. Which half of the state to base in, because trying to do both ends from one hotel is the mistake most people make. Which weekend to avoid the Bay Bridge. And the Assateague thing that catches families out every year, which I will get to.

Nicole Damiano, ASTA Verified Travel Advisor with FG Luxury Travel

Beyond the Bookshelf

A shelf of Maryland books and films, and one of them has sold millions of copies to children who have no idea the island is real.

Start with Misty of Chincoteague. It is the book that made the Assateague horses famous, it is still in print after eighty years, and a child who has read it will lose their mind when a horse walks past the car. Read it before you go, not after.

For the Bay itself, anything about watermen and crabbing. The culture on the Eastern Shore is a working one and it helps if kids understand that the boats are jobs rather than scenery.

For older children, a proper account of Harriet Tubman, who was born enslaved in Dorchester County and came back thirteen times to lead others out. The byway through that landscape means far more when they know the story first.

And for the anthem, the short version is worth telling in the car. A lawyer watching a British bombardment from a ship, a flag still flying at dawn, a poem scribbled on the back of a letter. Then you stand at Fort McHenry and look at where the ships were.

On screen, Baltimore has a whole film tradition of its own. Hairspray is the family friendly one and the kids will sing it the entire trip.

Why Maryland works with kids

Maryland works with children because the distances are short and the variety is high.

Nothing here is more than about three hours from anything else, so a week does not turn into a driving holiday. And the things at the end of the drives are different from each other in a way that keeps everyone interested. A city aquarium, a battlefield, a crab shack, a beach, a mountain lake, a fossil cliff.

It is also a cheap state to do well. A lot of the best things are free or close to it, and crabs by the dozen on a picnic table feed a family for less than a restaurant does.

Short drives. Baltimore to Annapolis is about forty minutes. Baltimore to Ocean City is under three hours. Baltimore to the western mountains is about three. You can see the whole state in a week without a hard day.

Wild horses you can see from the car. The Maryland end of Assateague has free roaming horses on the beach, in the dunes and on the road. No hike, no luck, no hide. You watch from a distance and do not feed them.

Crabs are an activity, not a meal. A table covered in paper, a pile of steamed blue crabs, a wooden mallet and two hours. Children who will not eat seafood will absolutely smash a crab with a hammer.

Fossils your kids can keep. The beach below Calvert Cliffs gives up fossil shark teeth millions of years old. Finding one is the best twenty minutes of most family trips here.

History that does not need a lecture. Fort McHenry, Antietam and the Tubman byway all tell themselves. The landscape does most of the work.

Maryland Place by Place

Nine places that between them make up almost every Maryland trip, running roughly west to east across a state you can cross in an afternoon.

The Inner Harbor in Baltimore seen from Federal Hill
01

Baltimore

Masts in the harbor at Annapolis, Maryland
02

Annapolis

The boardwalk at Ocean City, Maryland
03

Ocean City

Wild horses grazing in the dunes at Assateague Island
04

Assateague Island

The Hooper Strait Lighthouse at St. Michaels, Maryland
05

St. Michaels

Downtown Frederick, Maryland
06

Frederick

A cannon on the field at Antietam National Battlefield
07

Antietam

The cliffs at Calvert Cliffs State Park above the Chesapeake Bay
08

Calvert Cliffs

The shoreline at Deep Creek Lake in western Maryland
09

Deep Creek Lake

The Bay is the point

If you understand one thing about Maryland before you go, understand that the Chesapeake Bay is not scenery. It is the economy, the food, the weather and the identity.

It is the largest estuary in the United States and it cuts the state almost in half. Everything about how Maryland eats and works and gets around comes back to it. The watermen who crab and oyster it are doing a job their families have done for generations, and the skipjacks in the museums were working boats within living memory.

This matters practically, because it is why the state is split into two halves that feel different. The Western Shore has Baltimore, Annapolis and the suburbs of Washington. The Eastern Shore is flat, agricultural, slower, and reached by a bridge that becomes the most important four miles of road in the state on a summer Friday.

It also matters because of the crabs. Blue crab season runs roughly from spring into late autumn and the crabs are biggest and best in late summer. Outside that, what you are eating probably came from somewhere else, and anywhere honest will tell you so if you ask.

The Eastern Shore is also Harriet Tubman country. She was born in Dorchester County, escaped from it, and came back repeatedly to bring others out through the marshes you drive past. The visitor center at the state park there is free and it is one of the better pieces of interpretation anywhere in the country.

A table of steamed blue crabs with people picking them

Crabs are served on paper with a mallet and a lot of seasoning. It is messy, it takes hours, and it is the single most Maryland thing you can do with children.

Five things to eat in Maryland

Maryland food is Chesapeake food, which means crab, more crab, and a seasoning that goes on everything including the fries.

Old Bay is the thing to understand first. It is a spice blend from Baltimore, it is on the table everywhere, and locals put it on crab, shrimp, corn, fries, popcorn and the rim of a glass. Children either love it immediately or need it kept on the side, and there is no middle ground.

The second thing is the difference between a crab cake and a crab cake. A proper Maryland one is almost entirely lump crab meat with just enough binder to hold it. If it tastes mostly of breadcrumb, you are in the wrong place.

Steamed blue crabs covered in seasoning

Steamed blue crabs By the dozen, on paper, with a mallet. Two hours of work for a plate of food and worth every minute. Late summer is when they are biggest.

Maryland crab cakes plated with salad

A Maryland crab cake Lump crab with barely any filler, broiled rather than fried if you want the local version. Order it as a sandwich for a child.

A bucket of Thrasher's French Fries on the Ocean City boardwalk

Thrasher’s fries, Ocean City Sold on the boardwalk in a bucket with vinegar and no ketchup allowed. A boardwalk institution and a hill people will die on.

A slice of Smith Island cake showing its thin layers

Smith Island cake The state dessert. Eight to ten paper thin layers with fudge icing between every one, from an island in the Bay with a few hundred people on it.

Berger cookies, a Baltimore shortbread topped with thick fudge

Berger cookies A Baltimore cookie that is really a thick slab of fudge sitting on a small shortbread. Sold in every supermarket in the state.

A practical note on crabs. They are priced by the dozen and by size, the price moves with the catch, and a dozen large crabs plus corn feeds about three people. Order a half dozen first and add more. Bring wipes, and do not wear anything you care about.

The Assateague trap, and how to avoid it

This is the thing that catches families out every single year, and almost no other guide says it plainly.

Assateague Island has two ends and they are in two different states, and there is no road between them. The National Park Service says it outright: there is no vehicle access between the two entrances. To get from one end to the other you drive back to the mainland and all the way around.

The Maryland entrance is at the end of Route 611, about eight miles south of Ocean City. The Virginia entrance is at the end of Route 175, two miles east of Chincoteague. They are on the same island and they are a long drive apart.

The horses are split too, by a fence on the state line. The Maryland herd is managed by the National Park Service. The Virginia herd is owned by the Chincoteague Volunteer Fire Company and lives on the national wildlife refuge under a permit that caps it at about a hundred and fifty adults.

And the famous Pony Swim is the Virginia herd, not the Maryland one. It happens every July, on the last Wednesday before the last Thursday of the month, when the saltwater cowboys drive the ponies across the channel to Chincoteague. The foals are auctioned the next day and the adults swim back on the Friday. If that is the reason you are going, you want Chincoteague, Virginia, and you want to book a room a year out.

If you want horses on a beach with far fewer people, you want the Maryland end, and you can do it as a day trip from Ocean City.

Fees are separate too. The Maryland district is twenty five dollars per private vehicle for seven days, twenty for a motorcycle, and fifteen per person for anyone arriving on foot or by taxi, though a family traveling together never pays more than the vehicle rate. Walking or cycling in is free. The park annual pass is forty five dollars and it covers both districts plus Chincoteague refuge. Assateague State Park sits next door and is a separate thing with separate passes that are not valid in the national seashore.

Getting there, and which airport

Baltimore Washington International, which everyone calls BWI, is the obvious airport and it is one of the easier ones in the country to use. It sits between Baltimore and Washington with a rail station attached.

Washington Dulles and Reagan National are both options if the fares are better, and Reagan in particular is close enough to Annapolis and the Bay to work without a long transfer.

Philadelphia is worth checking if you are heading straight for the Eastern Shore and Ocean City, because it is about two and a half hours and avoids the Bay Bridge entirely.

You need a car. Baltimore, Annapolis and Ocean City are each walkable once you are in them, but nothing on this page connects to anything else without one.

BWI Thurgood Marshall. The default. Twenty minutes from Baltimore, forty from Annapolis, and it has a rail station for anyone connecting onward.

Washington Dulles and Reagan National. Both work for the western half of the state. Reagan is closer in and better for Annapolis and the Bay.

Philadelphia. About two and a half hours from Ocean City and it keeps you off the Bay Bridge. Worth a look if the Eastern Shore is the whole trip.

The Bay Bridge is the chokepoint. US 50 over the Chesapeake is the only road from the Western Shore to the Eastern Shore for a hundred miles. On a summer Friday afternoon it backs up for hours.

Cross early or cross late. Go east before about ten in the morning on a Friday, or after about eight at night. Coming back west, the same thing in reverse on a Sunday.

The twin spans of the Chesapeake Bay Bridge

The Bay Bridge is four miles of road and the single most important four miles in the state in July. Time your crossing or lose an afternoon to it.

Baltimore, and what to do with two days

Baltimore is better than its reputation and it is the easiest city in the mid Atlantic to do with children.

Everything you need is around the Inner Harbor and it is walkable. The National Aquarium is the headline and it is a very good one, with a rainforest at the top and a dolphin sanctuary. Buy tickets ahead with a time on them, because walk up availability in summer is poor.

Next door is the Maryland Science Center, which is hands on and aimed squarely at primary school age, and Port Discovery, which is for the under eights and will buy you three hours of peace.

Fort McHenry is a ten minute drive and it is the one I would not skip. It is a star shaped fort on a point of land, the flag that inspired the anthem flew here, and children can run the ramparts while you look at the water the British ships came up.

Then eat. Lexington Market is the old one and has been rebuilt. Fells Point is cobbles and pubs and crab houses and the easiest evening in the city.

Two days is right for Baltimore. Three if your children are museum children.

Baltimore has a reputation for crime that is both real and badly understood by visitors. The harbor, Fells Point, Federal Hill, Mount Vernon and Hampden are where you will spend your time and they are ordinary city neighborhoods. Do what you would do in any American city, park in a garage rather than on the street, and do not wander twenty blocks north at night.

Can you do Maryland without a car?

Partly, and better than most American states.

Baltimore and Annapolis work car free. BWI has a train station, the MARC and Amtrak both run into Baltimore Penn Station, and the city has light rail, a subway line and the free Charm City Circulator around the center. Annapolis is forty minutes by bus from Baltimore and is walkable once you are there.

Ocean City can be done without a car if you take the bus or train to Salisbury and connect, and once you are there the boardwalk tram and the municipal bus cover the whole strip.

What you cannot do without a car is Assateague, Antietam, Calvert Cliffs, St. Michaels or the western mountains. Those are all road trips and there is no alternative.

A reasonable compromise for a family without a driver is three nights in Baltimore and Annapolis by train, then a rental car for the second half.

When to go

May, June, September and early October are the best months here and it is not close.

July and August are hot and humid in a way that surprises people. The Bay does not cool anything down, the cities hold the heat, and afternoon thunderstorms are routine. It is also when every road east is full.

September is my pick. The water is still warm enough to swim, the crabs are at their best, the crowds go home after Labor Day, and Ocean City is still open but quiet.

May and June are green and comfortable, with crabs just starting and the battlefields at their best.

October is beautiful in the western mountains, with proper fall color around Deep Creek Lake and along the C and O Canal.

Winter is quiet. Baltimore and Annapolis work fine, Ocean City mostly shuts, and Deep Creek Lake turns into a small ski area. It is a different trip and a cheap one.

One date to know: the Chincoteague Pony Swim is in late July, and it fills every room within an hour of the island. If you are going to the Eastern Shore that week and the swim is not why, pick another week.

How Many Days & First-Trip Routing

How many days do we need in Maryland? Six nights is the right first trip, split between two bases. Two or three in Baltimore and Annapolis for the city, the aquarium and the fort, then three or four on the Eastern Shore for Assateague, Ocean City and the Bay.

Four nights works if you pick one half. Baltimore, Annapolis, Fort McHenry and a day in Frederick or at Antietam makes a good short trip without ever crossing the Bay Bridge.

Three nights is a city break with one day trip. Fine, but you will not see what the state actually is.

Eight to ten nights lets you add the western end, which almost nobody does. Deep Creek Lake, Swallow Falls, the C and O Canal and Antietam are a different state entirely from the beach.

How to Route a Maryland Week

The routing rule in Maryland is simple. Do not try to do both halves from one base.

The Bay Bridge is the only crossing, it is slow when you most want to use it, and an hour each way kills a day. Two bases, one on each side, is the whole trick.

Base one, Baltimore or Annapolis. Baltimore for the museums and the fort, Annapolis if you want somewhere smaller and prettier with boats. They are forty minutes apart so you can base in either and do both.

Base two, Ocean City or the Eastern Shore. Ocean City if you want a boardwalk and a proper beach town. St. Michaels or Cambridge if you want quiet, boats and the Tubman byway.

Cross the bridge at the right time. East on a Friday before ten in the morning or after eight at night. Back west on Sunday the same way round.

Day one, Baltimore. Inner Harbor, the aquarium with a timed ticket, dinner at Fells Point.

Day two, Fort McHenry and Annapolis. The fort in the morning, then the forty minutes to Annapolis for the afternoon and the waterfront.

Day three, cross and settle. Over the bridge, stop in St. Michaels for the maritime museum and lunch, then on to the coast.

Day four, Assateague. The Maryland end for the horses and the beach. Twenty five dollars a vehicle for seven days, so go twice.

Day five, Ocean City. The boardwalk, the beach, fries in a bucket, and the amusement piers at the south end.

Add a day for Calvert Cliffs. On the way back west if you are driving south of Annapolis. Fossil shark teeth on the beach and a two mile walk to get to it.

Where these places are

A map of every place named on this page, so you can see how close together they really are.

Assateague IslandDeep Creek LakeSt. MichaelsCambridgeOcean CityAnnapolisBaltimoreFrederickAntietamADVENTURESWESEEK.COM

Regions at a Glance

Baltimore and the Patapsco

The city, the Inner Harbor, Fort McHenry and the museums. Where most trips start and where the rain day plan lives.

Annapolis and the Western Shore

The state capital, the Naval Academy, sailing, and a historic center you can walk end to end in an afternoon.

The Eastern Shore

Flat, agricultural and slow. St. Michaels, Cambridge, the Tubman byway, working crab houses and very little traffic.

The Atlantic coast

Ocean City and Assateague. Boardwalk at one end, wild horses and empty sand at the other, eight miles apart.

Southern Maryland

Calvert Cliffs, Solomons and the tobacco country. Fossil hunting, small harbors and almost no visitors.

Western Maryland

Frederick, Antietam, the C and O Canal and Deep Creek Lake. Mountains, battlefields and fall color, about three hours from the beach.

A monument in the fields at Antietam National Battlefield

Antietam is the quietest famous battlefield in the country. Twenty three thousand casualties in one day and almost nothing built on it since.

Must See and Do

Assateague Island, Maryland end. Twenty five dollars per vehicle for seven days. Wild horses, a long empty beach and a short drive from Ocean City. Watch from a distance and never feed them.

Fort McHenry. The star fort where the anthem was written. Ramparts to run on, a short film that lands it, and the harbor in front of you.

The National Aquarium, Baltimore. Four floors, a rainforest at the top, a dolphin sanctuary. Buy a timed ticket ahead in summer.

Antietam National Battlefield. The bloodiest single day in American history, kept almost exactly as it was. Drive the tour route and stop at Burnside Bridge.

Calvert Cliffs State Park. A two mile walk to a beach where fossil shark teeth wash out of the cliffs. Kids find them. Do not climb the cliffs.

The Chesapeake Bay Maritime Museum, St. Michaels. A lighthouse you can go inside, working boats, and a boatyard where they are still restoring skipjacks.

The Harriet Tubman Underground Railroad Visitor Center. Free, in the Dorchester County marshes she was born in. One of the best pieces of interpretation in the country.

The Ocean City boardwalk. Three miles of it, a tram that runs the length, fries in a bucket, and amusement piers at both ends.

The C and O Canal at Great Falls. A boardwalk out over the Potomac to the falls, plus a towpath that runs a hundred and eighty four miles to Pittsburgh if you have bikes.

Swallow Falls State Park. Maryland’s tallest waterfall and an old growth hemlock forest, out west near Deep Creek Lake.

Doing Maryland With Children

Maryland is an easy state with children and most of the friction is weather and timing rather than logistics.

Book the aquarium ahead. Timed tickets, and summer walk up availability is poor. Do it the week you book the hotel.

Do not feed the Assateague horses. People are kicked, bitten and knocked down every year. Human food makes the horses sick and horses that beg at the road get hit by cars. Watch from the car or from well back.

Take water and a bucket to Calvert Cliffs. It is a two mile walk each way to the beach and there is nothing out there. A small sieve or a kitchen colander makes finding teeth far easier.

Crabs take two hours. Do not book anything after. Ask for a lesson on the first one, because every crab house will give you one.

Humidity, not heat, is the problem in July. Plan the outdoor things for morning, the indoor things for one to four, and expect a thunderstorm most afternoons.

Ticks on the battlefields and the towpath. Long grass, long summer. Check at the end of the day.

Ocean City is two towns. The south end is boardwalk, arcades and crowds. North of about 60th Street it is quiet residential beach. Pick the one you want before you book.

Who Maryland Suits, and Who Should Skip It

Maryland suits families who want several different kinds of day inside one short week. Beach, city, history, boats and mountains are all here and all close together.

It suits anyone with a child between about five and twelve particularly well. Crabs with a mallet, horses on a beach, fossils you keep, a fort you run around, an aquarium. It is a very hands on state.

It suits history minded families, and it does it without making anyone trudge. Fort McHenry and Antietam both work in about two hours.

It does not suit anyone looking for dramatic landscape. The Bay is lovely and the western mountains are pleasant, but nothing here will take your breath away the way the West does.

It does not suit a family that hates humidity and can only travel in July and August.

And it does not suit anyone expecting the Pony Swim at the Maryland end of Assateague, which is the single most common disappointment in this state.

Worth the Money in Maryland

The Assateague annual pass. Forty five dollars and valid a year across both districts plus Chincoteague refuge. If you are going twice, or doing both states, it pays for itself immediately.

A timed aquarium ticket. Worth the planning rather than the money. The queue in July for walk ups is the difference between a good morning and a wasted one.

Crabs at a proper crab house. More than you expect and worth it. Ask what came in today and how big. If they dodge the question, go elsewhere.

A night on the Eastern Shore rather than a day trip. The bridge is the whole argument. Two bases beats one base and four crossings.

Skip the Ocean City parking hunt. Park once in a garage or a lot for the day and use the boardwalk tram. Circling for a free space in July is a sport you will lose.

Skip the Inner Harbor chain restaurants. Walk fifteen minutes to Fells Point or Little Italy and eat better for less.

The Naval Academy tour, if you have a teenager. Guided, about an hour and a half, and the sort of thing a fifteen year old pretends not to enjoy and then talks about for a week.

A food stand on the Ocean City boardwalk

Three miles of boardwalk, a tram that runs the whole length, and fries sold in a bucket with vinegar and no ketchup.

Things That Surprise First Timers

There is no road between the two ends of Assateague. Same island, two states, no connection. You drive back to the mainland and around. This ruins more Maryland itineraries than anything else.

The Pony Swim is the Virginia herd. Not the Maryland one. A fence on the state line separates them and they have different owners.

Crabs are priced by the dozen and the price moves. There is no fixed menu price. Ask what today is before you order.

The Bay Bridge is the whole state’s traffic. One crossing for a hundred miles in either direction. Summer Friday afternoons are bad.

Baltimore is small and walkable. People arrive braced for a big dangerous city and find a compact harbor with everything within twenty minutes on foot.

Maryland has mountains. Three hours west of the beach there is a lake, a ski hill, a waterfall and old growth forest. Almost no visitor goes.

Old Bay goes on everything. Including the fries, the corn, the popcorn and the rim of the glass. It is not a garnish, it is a food group.

You can find real fossils on a public beach. Calvert Cliffs gives up shark teeth millions of years old to anyone willing to walk two miles and look down.

Where I Would Start

If you are starting from nothing, I would do this.

Six nights in September. Three in Baltimore, doing the aquarium, Fort McHenry and a day in Annapolis. Cross the Bay Bridge on a weekday morning, stop at St. Michaels for lunch and the maritime museum, then three nights on the coast.

Do Assateague on your first full day there, early, because the horses are more active and the parking lot fills. Buy the seven day vehicle pass and go back a second time.

Eat crabs once properly, at a table with paper on it, and give it the whole evening.

If you have a spare day on the way home, Calvert Cliffs for the shark teeth. Nobody regrets that one.

Maryland by the numbers

Facts to know before you go

$25Assateague, Maryland districtPer private vehicle, valid seven days. Walking or cycling in is free.
$45Assateague annual passValid one year and covers both the Maryland and Virginia districts plus Chincoteague refuge.
No roadBetween the two ends of AssateagueThe two entrances are in different states with no vehicle access between them.
~150Adult ponies, Virginia herdCapped by permit. The Maryland herd is separate and managed by the National Park Service.
Late JulyThe Chincoteague Pony SwimThe last Wednesday before the last Thursday of the month, with the foal auction the next day.
4 milesThe Chesapeake Bay BridgeThe only crossing to the Eastern Shore for about a hundred miles either way.
~2.5 hrsBaltimore to Ocean CityAnd about three hours from Baltimore west to Deep Creek Lake.
8 to 10Layers in a Smith Island cakeThe state dessert, from an island in the Bay with a few hundred residents.

Maryland is not one kind of trip

Maryland gets treated as one trip and it is at least four, which is why a week here works better than people expect.

The city and history trip

Baltimore, Fort McHenry, Annapolis, Frederick and Antietam. Four or five nights, no bridge crossing, easy in any season.

The beach and horses trip

Ocean City and Assateague with a night or two on the Eastern Shore. Four or five nights, best in June or September.

The Bay trip

St. Michaels, Cambridge, Solomons and the Tubman byway. Boats, crabs, marsh and almost nobody. The quietest version.

The mountain trip

Deep Creek Lake, Swallow Falls, the C and O Canal. Lake summers, fall color, and a small ski hill in winter.

What families come to Maryland for

Wild horses on a beach. Assateague, the Maryland end, with far fewer people than the Virginia side.

Crabs done properly. Paper, mallet, Old Bay, two hours and a very happy table.

A city that works with kids. Baltimore’s aquarium, science center and fort are all inside twenty minutes of each other.

History that does not need effort. Fort McHenry, Antietam and the Tubman byway, all within ninety minutes of Baltimore.

Fossils you keep. Shark teeth on the beach below Calvert Cliffs.

A boardwalk that has not changed. Ocean City, three miles, a tram, arcades, and fries in a bucket.

Short drives. Mountains to ocean in about two and a half hours. Nothing here is far from anything.

Only in Maryland

Wild horses on the shore at Assateague Island

Two herds, one island

The fence on the state line

Assateague’s horses are split by a fence at the Maryland and Virginia border. The Maryland herd belongs to the National Park Service. The Virginia herd belongs to a volunteer fire company and swims the channel every July.

A tall slice of Smith Island cake on a plate

Eight layers, maybe ten

Smith Island cake

The state dessert comes from an island in the Chesapeake with a few hundred people on it, reachable only by boat. Thin layers of yellow cake with fudge icing between every one.

The Welcome to Ocean City sign on the boardwalk

Vinegar only

The bucket of fries

On the Ocean City boardwalk the fries come in a bucket with vinegar, and asking for ketchup is a known way to identify yourself as a visitor.

Combine It With

Chincoteague, Colonial Williamsburg and Shenandoah are all an easy add. The other end of Assateague is in Virginia.

Gettysburg is about an hour from Frederick and pairs naturally with Antietam. Philadelphia is two hours from Baltimore.

Forty minutes from Annapolis and free museums all week. The obvious pairing for a first trip.

North along the coast for Rehoboth and Bethany, and no sales tax on anything you buy there.

Fort McHenry in Baltimore

Tell me who is coming, and when.

Tell me who is coming, how old they are, and when you can travel, and I will tell you which half of the state to base in and how to time the bridge. Maryland is a week that works beautifully when the routing is right and a lot of driving when it is not.

Maryland, Answered

The ones that come up in almost every planning call. If yours is not here, ask me.

How many days do you need in Maryland?

Six nights for a proper first trip, split between two bases so you only cross the Bay Bridge once each way. Four nights works if you stay on one side. Eight to ten lets you add the western mountains, which almost nobody does.

Can you drive from the Maryland end of Assateague to the Virginia end?

No. There is no vehicle access between the two entrances. The Maryland entrance is off Route 611 south of Ocean City and the Virginia entrance is off Route 175 near Chincoteague, and getting from one to the other means driving back to the mainland and around.

Where do you see the Assateague wild horses?

Both ends of the island have them, and they are separated by a fence on the state line. The Maryland end is quieter and easier to reach from Ocean City. The Virginia herd, on the Chincoteague refuge side, is the one from the Pony Swim.

When is the Chincoteague Pony Swim?

Every July, on the last Wednesday before the last Thursday of the month, at slack tide. The foal auction is the following day and the adult ponies swim back on the Friday. Rooms anywhere near Chincoteague go a year ahead for that week.

How much does Assateague cost?

In the Maryland district, twenty five dollars per private vehicle for seven days, twenty for a motorcycle, and fifteen per person for anyone arriving on foot or by taxi, though a family traveling together pays no more than the vehicle rate. Walking or cycling in is free. The annual pass is forty five dollars and covers both districts plus Chincoteague refuge.

Where should we stay in Maryland with kids?

Two bases. Baltimore or Annapolis for the city half, then Ocean City or somewhere on the Eastern Shore for the beach half. Trying to do both from one hotel means four Bay Bridge crossings and a wasted afternoon each time.

What is the best month to visit Maryland?

September. The water is still warm, the crabs are at their best, the crowds go after Labor Day and Ocean City is still open. May, June and early October are all good too. July and August are hot, humid and busy.

Is Baltimore safe with children?

The areas visitors use are ordinary city neighborhoods. The Inner Harbor, Fells Point, Federal Hill, Mount Vernon and Hampden are where you will spend your time. Park in a garage rather than on the street and use the same judgment you would in any American city.

What is a Maryland crab cake supposed to be?

Almost entirely lump crab meat with just enough binder to hold it together, usually broiled rather than deep fried. If it tastes mostly of breadcrumb and filler, you are not eating the local version.

Can you find shark teeth at Calvert Cliffs?

Yes. Fossil teeth millions of years old wash out of the cliffs onto the beach and people find them most visits. It is a two mile walk each way from the parking area and you are not allowed to climb the cliffs, which are unstable.

Photo credits

Au Kirk / CC BY 2.0 · Baron Maddock / CC BY 4.0 · Bohemian Baltimore / CC BY-SA 4.0 · Chris Light / CC BY-SA 3.0 · ConneeConehead101 / CC BY-SA 4.0 · Don Kasak / CC BY-SA 2.0 · Doug Kerr from Albany, NY, United States / CC BY-SA 2.0 · Fletcher6 / CC BY 3.0 · Joshua Davis from United States of Ameri / CC BY-SA 2.0 · Ken Lund from Las Vegas, Nevada, USA / CC BY-SA 2.0 · Lee Cannon / CC BY-SA 2.0 · Mbinebri / Matthew Binebrink / CC BY-SA 4.0 · Missvain / CC BY 4.0 · Nicolas Raymond from Bethesda, Maryland, / CC BY 2.0 · PLBechly / CC BY-SA 4.0 · Steve Snodgrass / CC BY 2.0 · bigbirdz / CC BY 2.0 · danperry.com / CC BY 2.0 · delgaudm / CC BY 2.0 · m01229 / CC BY 2.0 · tramod / CC BY 2.0. All via Wikimedia Commons and Openverse. Remaining photographs on this page are public domain.