4 Days in Edinburgh: Kinda Creepy, Really Cool

And almost immediately after arriving, I started wondering: Why aren’t more people talking about this place?

Edinburgh is dramatic. A massive medieval castle sits high above the city, seeming to watch you from almost everywhere you go. Dark stone buildings line steep streets and narrow closes. Gothic spires puncture the skyline. There are monuments and churches and centuries-old gravestones seemingly everywhere you turn.

And Edinburgh is old. Really old.

I happened to visit as the city was celebrating its 900th anniversary. 900! St. Giles’ Cathedral has stood at the heart of the city in some form since the 12th century. You can walk through closes where Edinburgh’s residents once lived in unimaginably crowded conditions. Greyfriars Kirkyard dates to the 1500s. And the Grassmarket—today filled with pubs, cafés and tourists—was once the site of public executions.

Edinburgh is a city of contrasts. Dark and dramatic, but incredibly beautiful. Ancient and eerie, but lively and full of energy.

There is a darkness to Edinburgh. A little gloom. A little creepiness. And when the Scottish clouds roll in over all that stone and Gothic architecture, the city seems perfectly happy to lean into it.

And somehow, that’s what makes it so beautiful.

I spent four days completely fascinated by Edinburgh—walking through castles and kirkyards, down cobblestone streets and underground closes, eating haggis, drinking flat whites, listening to stories that were sometimes hundreds of years old and occasionally wishing I hadn’t heard them right before bed.

I had never been anywhere quite like it.

And Edinburgh, which hadn’t even been on my list, very quickly became a city I couldn’t believe wasn’t on everyone else’s.

Day One — Getting Acquainted with Edinburgh

As you probably know by now, I have a pretty standard routine for arrival day. Drop the bags at the hotel, find some coffee, and start walking.

We were staying right on the Royal Mile, which turned out to be a little loud but incredibly convenient. We dropped our bags, fought the urge to give in to jet lag, and headed out to get our bearings.

Our first stop was The Milkman, an impossibly cute little coffee shop that quickly became our go-to every morning of the trip. They made a fantastic flat white, which is important. I visit Starbucks plenty at home, but there is nothing worse than traveling thousands of miles only to end up drinking the same coffee you could have had around the corner.

Flat whites in hand, we headed toward Princes Street Gardens, a beautiful green park smack in the middle of the city.

The gardens separate Edinburgh’s Old Town from its New Town, with Waverley Station at one end and Edinburgh Castle towering above the other. In between you’ll find museums, the picturesque Ross Fountain and an incredible view of the Scott Monument—the very monument that had started this whole trip in the first place.

We wandered leisurely through the gardens, bought a second coffee at the outdoor café and took about a dozen pictures of Edinburgh Castle looming over us from high above the park.

Looming is a word I’m going to use a lot when talking about Edinburgh.

The castle doesn’t simply sit above the city. It dominates it. You catch glimpses of it between buildings and at the ends of streets, perched dramatically on top of Castle Rock. It’s beautiful and imposing and maybe even a little ominous.

In other words, very Edinburgh.

We still had time to kill before check-in, so we headed back into Old Town and walked through the Grassmarket. Today, it’s one of Edinburgh’s liveliest areas, lined with colorful pubs, bakeries, ice cream shops and tourists.

But the Grassmarket has a much darker history. For more than a century, people gathered here to watch public executions. Now you can grab a pint and an ice cream.

From the Grassmarket, we headed up Victoria Street, the colorful, curving street often associated with Harry Potter’s Diagon Alley. We took another dozen or so pictures, passed a popular Harry Potter shop, and popped into The Knight’s Vault, a shop selling handmade and antique swords and armor.

I have never been particularly interested in swords or weapons, but put them inside an atmospheric shop in medieval Edinburgh and, as it turns out, I can browse for thirty minutes.

Eventually, jet lag started winning, so we headed back to the hotel to check in, shower, rest and regroup.

That evening, we kept things simple. I don’t like making big plans or reservations for arrival night because you never quite know how you’re going to feel—or whether your travel day will even go according to plan.

So we went for something casual and quintessentially Scottish: fish and chips.

And because apparently fish and chips weren’t Scottish enough, we also ordered haggis—a traditional Scottish dish made with minced and seasoned sheep innards, which in our case arrived breaded and deep fried.

It was…interesting.

But as I always say: when in Rome. Or Edinburgh.

We finished the night with one of our favorite travel rituals, wandering through a local grocery store to see what flavors of chips and candy we couldn’t get at home and stocking up on snacks for the hotel room.

Then, after successfully powering through our first jet-lagged day, we called it an early night.

One day into Edinburgh and we’d already had a medieval castle looming over our heads, walked through a former execution site, browsed antique swords, eaten haggis and discovered a coffee shop we’d return to every morning.

Not bad for a city that hadn’t even been on my radar.

Day Two — The Royal Mile

Day two was a full one.

We spent most of it getting to know Edinburgh’s most famous street, the Royal Mile. It runs through the heart of Old Town, from Edinburgh Castle at the top all the way downhill to Holyrood Palace at the other end. In between, it’s lined with shops, pubs, restaurants and attractions, with street performers drawing crowds along the way.

We started our morning at the incredible St. Giles’ Cathedral.

Still an active church today, St. Giles’ has been at the heart of Edinburgh for more than 900 years. It was free to enter when we visited, and we spent about half an hour wandering through the beautiful medieval interior.

I’ve been inside a lot of churches in Europe. A lot.

And St. Giles’ might be my favorite.

That’s saying something for a person who has stood inside St. Peter’s Basilica at the Vatican.

Don’t miss it.

From there, we headed uphill for our timed entry at the crown jewel of the city: Edinburgh Castle.

Remember what I said about the castle looming over Edinburgh?

Up close, it’s even more impressive.

Edinburgh Castle absolutely takes over the city’s skyline. From nearly every corner of Old Town, you can look up and there it is, sitting dramatically atop Castle Rock and looking down over everything below. And once you finally make your way up there, you get to do the same.

The views are incredible.

But the castle itself is just as fascinating. It has stood in some form for centuries and has served as a royal residence, military fortress and prison, among other things. We spent about two hours wandering through the grounds and exhibits, taking in the history—and, of course, taking far too many pictures.

If you happen to be at the castle around 1 p.m., stick around for the One O’Clock Gun.

The tradition began as a time signal for ships in the harbor, and the cannon can still be heard across the city today. We had already left the castle by the time it fired and heard it from elsewhere in the city. So if you find yourself at the castle at the right time, do what we didn’t and stick around for the up-close-and-personal version.

After the castle, we started slowly making our way downhill along the Royal Mile.

And slowly is the way I recommend doing it.

Holyrood Palace was our next official destination, but everything between the two was up to us. We wandered into shops. We stopped to watch a street magician balancing on a unicycle while making small objects disappear beneath a handkerchief. We grabbed pulled-pork sandwiches from Oink for lunch.

Somewhere along the way, we detoured into a small cemetery just off the Royal Mile and randomly stumbled across the grave of Adam Smith, the Scottish economist and author of The Wealth of Nations.

Little did I know, this would be the first of many cemeteries on this trip.

Eventually, we reached Holyrood Palace at the opposite end of the Mile.

We took a self-guided audio tour through the palace, the official Scottish residence of the British monarch. Both the palace and its grounds are beautiful, and the tour gives you another hefty dose of Scottish history along the way.

It’s worth making the walk all the way down.

But if you only have time for one end of the Royal Mile?

Go to the castle.

Going Underground

With the Royal Mile conquered, our day was only half done.

That evening, we had dinner at the Michelin-and-Kara-recommended Dulse in Edinburgh’s West End before walking back toward the Royal Mile for an evening tour of Real Mary King’s Close.

And this is where we got our first real taste of Edinburgh’s creepy side.

Closes are the narrow lanes and alleyways that branch off the Royal Mile, running steeply downhill between the buildings of Old Town. Centuries ago, they were packed with homes and businesses, and named for the prominent residents who lived there. Mary King was a widowed mother and successful fabric merchant who lived on the close in the 1600s.

Today, part of Mary King’s Close survives beneath the Royal Mile, hidden under the buildings of modern Edinburgh.

You descend from the busy street above into a dark collection of narrow passageways, former homes and stone streets. Costumed guides lead you through the preserved close while telling stories about the people who actually lived there—stories involving poverty, appalling sanitation, disease and, because Edinburgh hadn’t creeped me out quite enough yet, the bubonic plague.

Edinburgh suffered its worst outbreak of plague in 1645, and the incredibly crowded living conditions in Old Town helped disease spread quickly through its closes. Back then, people didn’t understand what we know now about how germs spread. They blamed bad air and foul smells. In reality, fleas carried by rats played a major role in transmitting the disease.

Creepy in theory. Considerably creepier when you’re standing underground in the dark where people actually lived through it.

The tour is wonderfully atmospheric without feeling like a cheesy haunted house. The period-costumed guide was first-rate, and what made the whole experience so unsettling was that beneath all the theatrical storytelling was the knowledge that these were real streets, real homes and real people.

It was fascinating. It was creepy.

I loved it.

Don’t go if you’re claustrophobic.

But if you’re not—and you like your history with a little darkness—absolutely go.

After spending our evening underground hearing stories about plague, poverty and death, we emerged back onto the Royal Mile and returned to our very comfortable hotel room.

Where I proceeded to lie awake thinking about all of it.

Apparently, there are consequences to loving Edinburgh’s creepy side quite this much.

Day Three — Stirling

After spending the previous evening underground listening to stories of plague, poverty and death, we woke up on day three ready to get out of town.

One of the great things about Edinburgh is how easy it is to use as a base for exploring more of Scotland. Waverley Station sits right in the middle of the city, with trains connecting you to towns throughout the country. From Waverly, many travelers visit the highlands or connect to London after their time in Edinburgh.

We chose Stirling, about 45 minutes away by train, for two reasons: Stirling Castle and William Wallace.

If your knowledge of William Wallace begins and ends with Braveheart like me, you are not alone. But the real Wallace was a leader in Scotland’s fight against English rule during the Wars of Independence, and Stirling was the site of the victory that made him famous.

In 1297, Wallace led a Scottish army against a larger English force at the Battle of Stirling Bridge. Stirling mattered enormously because controlling the crossing of the River Forth—and the castle overlooking it (the one I was on my way to see!)—meant controlling one of the most important routes in Scotland. Wallace and his army waited as part of the English army crossed the narrow wooden bridge before attacking, turning the crossing into a bottleneck. The result was a stunning Scottish victory and one of the defining moments of Wallace’s story.

My partner is a William Wallace fan, so Stirling was high on his list.

I was mostly there for the castle.

After grabbing a flat white for the road from The Milkman, we walked to Waverley, boarded our train and watched Edinburgh give way to the Scottish countryside.

Once in Stirling, we started the walk through town and uphill toward the castle.

Just before reaching it, we came across the Church of the Holy Rude, another centuries-old church.

Behind it was an enormous cemetery.

Because cemeteries were becoming something of a theme on this trip.

We walked straight through it on a narrow paved path, reading names on weathered headstones while heavy Scottish clouds hung overhead.

Creepy and beautiful. Again.

Then we reached Stirling Castle.

And Stirling Castle was magical.

It doesn’t have quite the same imposing presence as Edinburgh Castle, but what it does have are extraordinary views. From its walls, we looked out over rolling Scottish countryside dotted with sheep and wildflowers in one direction—and one of the creepiest cemeteries I’d ever encountered in the other.

So there I was, standing on the walls of a centuries-old Scottish castle with sheep and wildflowers on one side and weathered gravestones beneath heavy clouds on the other.

Beautiful. Gloomy. Grand. Creepy. Completely captivating.

We certainly weren’t in Kansas anymore.

We spent a couple of hours moseying around the castle and its grounds, taking picture after picture before heading back downhill into the center of town for lunch.

We stopped at a cute little café called Brea—which I recommend—and then mapped out our route to Stirling Bridge.

This was the part my William Wallace fan had been waiting for.

And…it was a bit of a letdown.

We walked out to Stirling Old Bridge expecting—well, I’m not entirely sure what we were expecting. Something that screamed WILLIAM WALLACE WAS HERE, perhaps.

Instead, we found a quiet old stone bridge over a narrow portion of the River Forth.

Pretty? Yes.

Dramatic? Not especially.

Here’s something useful to know. This isn’t actually the bridge from the famous 1297 battle. The current stone bridge was built roughly two centuries later. So, it’s still really old but as a sightseeing stop?

Unless you’re a serious William Wallace fan—I think you can skip it.

Back to Edinburgh—and Back Underground

We headed back to Edinburgh with plans for even more creepiness that evening.

After a quick dinner and a little rest at the hotel, we met our guide for an evening tour of Greyfriars Kirkyard and the Edinburgh Vaults.

Yes, another cemetery.

At this point, cemeteries had officially become something of a theme.

I definitely visited more cemeteries during four days in Edinburgh than I had during the rest of my life combined.

But Greyfriars was different.

As evening settled over the city, we walked through the centuries-old kirkyard, past elaborate monuments and worn headstones while our guide told us stories about some of the people buried beneath our feet.

This was Edinburgh’s dark side at its atmospheric best.

Old stone. Darkening skies. Centuries of history. A guide telling stories about dead people while you’re literally standing among their graves.

Edinburgh really does make it easy to give yourself the creeps.

Before heading underground, we made a quick stop to visit the kirkyard’s decidedly less-creepy resident: Greyfriars Bobby, the little dog famously remembered for remaining devoted to his master’s grave. We snapped the obligatory photo with his statue outside the pub that bears his name and then continued on toward our final stop of the night.

The Edinburgh Vaults.

Because apparently one creepy underground tour on this trip wasn’t enough.

Once again, we headed underground.

The difference between the Vaults and Mary King’s Close was immediately apparent. Mary King’s Close felt like stepping into a preserved piece of old Edinburgh. The Vaults felt darker. Rougher. More mysterious.

Stone chambers opened into other stone chambers. Passageways disappeared into darkness. There were no windows, very little light and absolutely nothing about the place that made me want to be there alone.

Our guide leaned into the stories and mood of the place.

And standing in those dark underground chambers at night, it didn’t particularly matter whether I believed every ghost story I was hearing.

I was creeped out. Completely.

We eventually climbed back above ground into modern Edinburgh, where there were lights and people and, importantly, no dark underground chambers.

Then I returned to my very comfortable hotel for another night of lying awake thinking about everything I’d just seen.

For someone who claimed to be creeped out by Edinburgh, I seemed to be remarkably committed to doing creepy things there.

Day Four — Edinburgh’s Fairytale Side

After three days of castles, graveyards, underground closes and generally giving myself the creeps, Edinburgh had one more side to show me.

And then we walked into a fairytale.

We started our final morning in Dean Village, an impossibly idyllic little pocket of Edinburgh tucked along the Water of Leith.

And when I say little village, I mean it really feels like a village. Beautiful old buildings sit along the water, surrounded by greenery, and everything feels quiet and peaceful and completely removed from the city.

Except you’re not.

You’re only minutes from the center of Edinburgh.

Somehow we had gone from the busy streets of downtown to a place that felt like we’d wandered into the Scottish countryside without ever really leaving the city.

Dean Village is mostly residential, and you can feel that when you’re there. We walked through slowly, taking pictures and admiring how beautiful it was, but I also had this strange feeling that we were intruding on someone else’s very peaceful life.

You wanted to stay. But also maybe leave these poor people alone.

From Dean Village, we picked up the Water of Leith Walkway and followed it toward Stockbridge.

This ended up being one of my favorite walks of the trip.

The path was wooded and peaceful, following the water while locals walked their dogs and jogged alongside tourists like us.

And the weather finally decided to become properly Scottish.

We had gotten incredibly lucky for most of the trip, with a mix of sunshine and clouds and virtually no rain. But on our last day, the sky turned gray and we got the occasional light drizzle as we walked.

I loved it.

Maybe that’s strange to say about rain on vacation, but it felt right. The gray sky, the damp greenery, the old stone buildings—it looked and felt exactly like Scotland was supposed to look.

The drizzle came and went as we made our way into Stockbridge, a neighborhood that immediately felt more local than touristy. It’s a little hip, a little chill, and the kind of place where people actually seem to live their everyday Edinburgh lives.

We happened upon a small farmers market as we walked through and wandered around for a bit before continuing on.

I remember thinking that if I lived in Edinburgh, maybe I’d live in Stockbridge.

From there, we made our way to Circus Lane, a tiny cobblestone street I’d seen all over social media and had specifically put on my list.

It’s every bit as Scottish-looking as the pictures suggest—ivy and moss, stone cottages and greenery lining a narrow lane. We stopped, took our pictures and moved on.

It’s lovely.

Would I cross the entire city just to see it? Probably not.

But we were already there, and it fit perfectly into the walk.

By this point, our occasional drizzle was becoming a little more persistent, but we kept going. This entire route—from Dean Village along the Water of Leith, through Stockbridge and Circus Lane—had been one long walk, and we had one final destination.

Calton Hill.

We climbed to the top for one last look at Edinburgh.

And I can’t think of a better place to have ended our sightseeing.

From up there, the city stretched out beneath us—the skyline, the monuments, the cemeteries and so many of the places we’d spent the previous four days exploring. The clouds had grown heavier by then, hanging low over the city and making everything look appropriately dramatic.

Very Scottish. Very Edinburgh.

Four days earlier, this had been a city that wasn’t even on my radar.

Now I was standing above it, looking out over a place that had completely surprised me.

We’d spent many hours walking that morning, and by the time we finally made it back to our hotel, we were a little soggy and very ready to dry off.

Later, we headed back out for one final wander along the Royal Mile, picked up a few souvenirs and ended our trip with a casual dinner at The City Cafe.

And because one serving of haggis apparently wasn’t enough for this trip, we ordered it again.

Not because the first one had suddenly turned me into a haggis enthusiast.

But because, when in Rome. Or, for the second time, Edinburgh.

A Lesson in Contrasts

I went to Edinburgh because a picture of the Scott Monument happened to catch my attention.

I left wondering why more people—especially Americans—aren’t going.

Edinburgh was one of those trips that just worked. Four days felt full without feeling frantic. There was always something else to see, but we had time to wander, stop for coffee, watch street performers, take the long way somewhere and occasionally find ourselves in yet another cemetery.

And I never got tired of looking at the city.

Edinburgh is a city of contrasts.

Dark and beautiful. Ancient and alive. Creepy and idyllic. Gloomy and colorful. Grand and intimate.

It can feel almost ominous when Edinburgh Castle is looming above you or you’re wandering through a centuries-old kirkyard under a gray Scottish sky. And then, minutes later, you’re walking beside the water through a quaint village that looks like something out of a fairytale.

Somehow, it all belongs together.

I think that’s what I loved most about Edinburgh. The darkness doesn’t take away from its beauty. It’s part of it. The old stone, the gray skies, the castles and kirkyards, the closes and cobblestone streets—they give Edinburgh a mood and a sense of place that I’ve never experienced anywhere else.

It’s dramatic. A little gloomy. Definitely a little creepy.

And completely beautiful.

Edinburgh wasn’t high on my list before I went. Now it’s a city I recommend all the time—and one I’d happily return to myself.

But mostly, it’s a place I still think about because I’ve simply never been anywhere else quite like it.