Toledo Spain Halloween Weekend 32Can you believe that’s Spain?! Cause I couldn’t. When I looked out of the plane window and saw this landscape stretch out for miles, I wouldn’t have been able to tell you where we were in the world, had I not known my final destination.

Megan’s Birthday shenanigan’s were the focus of the weekend alongside HALLOWEEN. Headed to Toledo Spain for the first night, we would come back to Madrid just in time for some Halloween dress up and fun.

I’ll be completely honest with you before we go any further. This post is 95% about Toledo Spain. I didn’t take very many photos while I was in Madrid although I did do a walk about of the city. Our Halloween photos are from there, but that’s about it.


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With traffic it took us almost 2 hours to get there, but the drive was enjoyable.

Arriving at the airport Megan and Will had prepared a party bus to take us straight out of the city and to Toledo. This is something I’ve been meaning to talk about. Shuttle services from airports. 

In my experience when you just take a few moments to book ahead, you can get a shuttle service (vans that drive big groups of people) or even hire cars to take you where you need to go, and normally at a much lower price and hassle than waiting for a taxi. Plus, you normally always feel like a baller because they’ll have someone waiting for you the moment you step off the plane. They’ll direct you straight to the car, and it’s much less hassle. Most cities offer a service like this, just google it.

Arriving in Toledo and taking a short walk to our hotel (the roads weren’t big enough for the van), we dropped off our luggage and went out to explore the city in the suns dying light.

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Toledo Spain Halloween Weekend 43Primly set atop Castilla-La Mancha, Toledo became an important Roman colony in 193 B.C. Toledo represents Spanish culture and was deemed a UNESCO World Heritage site in 1986.

Looking at the town you can see it is a network of connected walkways and alleys some fit cars and some don’t, we found that out the hard way! It’s all cobbles and old style houses throughout. So much fun to run around in. A complete maze when you just go. Don’t worry as soon as you come out at a side road its easy to see where you are.

Toledo Spain Halloween Weekend 3The cathedral was begun in 1226, commissioned by King Ferdinand III it is made in the gothic style some say, the most gothic of gothic styles.

Toledo Spain Halloween Weekend 4Our view from the roof of the hotel. For about $70 per night per person we stayed in the center of the city just a 5 minute walk from the Cathederal.

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Toledo Spain Halloween Weekend 7Pictures of people taking pictures, reverse selfology.

Toledo Spain Halloween Weekend 8Only Will caught on and played the part, over exaggerating his picture taking to the max.

Toledo Spain Halloween Weekend 10 Toledo Spain Halloween Weekend 11The gothic style is really cool when you look at it up close and personal.

Toledo Spain Halloween Weekend 12After stopping to admire all of the handy work, we continued past the Cathedral and fell into the side streets. Walking along past the vendors we leisurely strolled, stopping for snacks and drinks here and there, whatever caught our fancy.

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Toledo Spain Halloween Weekend 13Ain’t nothing but a hound dog!

Toledo Spain Halloween Weekend 14As you meander by the shop windows it was easy to see that steel is a prominent ware in this city. In my research I found that steel and particularly swords have long been famous in Toledo, mentioned as early as the 1st century BCE.

Toledo Spain Halloween Weekend 15As the sun started setting we broke off into smaller groups and some went for shopping, some went for drinks, and I headed back to the hotel to sit on the roof terrace overlooking the city, sipping on a G&T and calling family and friends. The perfect start to the evening.

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Toledo Spain Halloween WeekendMegan is ready for her Birthday dinner! On the terrace overlooking the cathedral.

She was in the mood for Tapas for dinner and a reservation at La Abadia in central Toledo did just the trick.

We ordered tapas until our stomachs couldn’t possibly hold another bite and then slowly made our way outside deciding to stop in at a bar with a live band! I hadn’t heard a good live band in awhile so was excited to enjoy it. Here we lost everyone in the group who decided to check out a few other places on the way back to the hotel, it had grown quite late.

Once the gin starts flowing my night has officially begun so we listened to the band until they finished and then heard that Taylor had just made it into town, the last of the group to arrive so we decided to go pick him up and continue the party out and about.

I stayed out with them because they promised me a sunrise in the morning. A promise of which, they DID NOT KEEP. I even kept my end of the bargain and went over to wake them up at which point I got the door shut in my face. Who needs them anyway?


Toledo Spain Halloween Weekend 16It’s true that if you wake up at sunrise in Toledo and throw open the shutters a disney song will play as birds tweet and swoop about. Try it while visiting and see if the same thing happens for you. 😉

Toledo Spain Halloween Weekend 17Amanda woke to join me and so we started by skirting the outter rim of the city. We were looking to see if we could cross the river for the ultimate view, like you saw in the painting of Toledo above. If there’s one thing I’ve learned about blogging, it’s always about the view!
Toledo Spain Halloween Weekend 18There weren’t many people out walking this early giving us the feeling that we had the whole city to ourselves, one that I reveled in.

Toledo Spain Halloween Weekend 19 Toledo Spain Halloween Weekend 20 Toledo Spain Halloween Weekend 21 Toledo Spain Halloween Weekend 22Castle on a cloud over there.

Toledo Spain Halloween Weekend 23 Toledo Spain Halloween Weekend 37Old style doors. Love em’!

Toledo Spain Halloween Weekend 24Which brings me all the way around to Don Quixote. You may have heard of the book?

Considered one of the most influential works of literature from the Spanish Golden Age, the story follows the adventures of a nameless Spaniard who reads so many chivalric romances he decides to set out to revive chivalry itself by undoing wrongs and bringing justice to the world.

Recruiting a farmer named Sancho Panza as his squire, he often employs a unique, earthy wit in dealing with Don Quixote’s ridiculous ideas of knighthood. It is easy to see that Don Quixote is far removed from the real world as he lives out his tales of knighthood.

Toledo Spain Halloween Weekend 40 Toledo Spain Halloween Weekend 25Graffiti.

Toledo Spain Halloween Weekend 39Sun’s perfectly rising.

Toledo Spain Halloween Weekend 26 Toledo Spain Halloween Weekend 38Yoga poses in front of old doors. Best part of the morning!

As the sun rose higher we headed back up the hill to our hotel and had breakfast then stopped in to see how Tweedle Dee and Tweedle Dum were doing. They still weren’t out of bed yet!

After everyone had woken and had breakfast it was time to head back towards Madrid. Except I still wanted that shot of Toledo. Taylor offered to drive over in his rental car so I could see the view from across the river so we were a bit behind the others on the way back. Kyle joined too.


Toledo Spain Halloween Weekend 27 Toledo Spain Halloween Weekend 28 Toledo Spain Halloween Weekend 30Love the view from over here!

Toledo Spain Halloween Weekend 30Getting back into the car we decided we would off road it to Madrid, you know, take the back roads and do some off the beaten path travel. Of all the places to do something like that, this was not it. There was nothing but pastures before us and before long we were back on the highway booking it into the city.


After some galavanting around the city all afternoon with even more amazing foods and multiple pitchers of cava sangria, we headed back to the hotel to get ready for Halloween night. And guess what??! We were all dressing up like DISNEY Characters 🙂

Halloween in Madrid SpainThe lot of us: Snow White and Prince Charming, Belle, Aladdin and Jasmine, Marry Poppins, Shrek, and Tweedle Dee and Tweedle Dum (for real)

Halloween in Madrid Spain 4Ugh, Belle just wants to have fun! Or read a book, not sure which?
Halloween in Madrid 5Turns out we were local celebrities. We couldn’t walk 2 feet without being swarmed by people who thought it was Disney Land. It was Soo fun! There was even someone dressed like the evil queen for Snow White! haha.

Madrid Spain for Halloween!We had opted to sign up for a pub crawl and I don’t want to end this post on a bad note but it was awful. It was so bad it was like projectile vomiting after accidentally drinking spoiled milk. They tried to bamboozle us by only giving drinks at a bar that had no room to move, then they made us get on buses and took us outside of the city to a club with no return trip intended.

Statistically, Spain has one bar for every 132 people of its 47.2 inhabitants so can somebody please explain to me why we would need to drive 40 minutes out of the city to go to some shitty club that there was no return journey from? Whoever coordinated this is a scheming piece of shit and should be fired on the spot. If we hadn’t bought tickets to the event in a square and if I knew of the company name, I would slander it. As it turns out I don’t know it BUT seriously the planner for this event sucks balls. Whatever you do, DO NOT go on a pub crawl in Madrid Spain for Halloween. I vehemently recommend against it. The End.

This article appeared first on The Cassey Excursion.





P.S. In the early afternoon on the next day we headed to the airport and wouldn’t you know, Scott was just coming back from a conference in the states and Sneaky Mom’d us in the Madrid airport. As in, he snuck up on us when we least expected it!