Stone Walls, Mud Trails, and Estonian Magic
Tallinn, Estonia arrives like a plot twist.
After weeks of weaving through Scandinavia’s clean minimalism and Nordic quiet, stepping off the ferry from Helsinki on August 29th felt like tumbling into a different chapter—one stitched together from post-Soviet grit, EU practicality, and the kind of charming old-world atmosphere that makes your brain toggle between centuries. Riding into the outskirts, the apartment blocks carried that unmistakable Soviet geometry: unfussy concrete, straight lines, an air of endurance rather than elegance. Threaded through it all were bright signs of the present; bike lanes, clean trams, cleverly repurposed old industrial spaces. It felt lived-in, not polished; expressive, not curated.
Tallinn’s Old Town, however, has a flair for drama. The place is basically a fortified time capsule. A settlement has existed here since at least the early medieval period, but Tallinn really began to flourish in the 13th century when it became a key Hanseatic trading port. The city walls grew taller, the towers multiplied, and the same fortifications still wrap the city like a stone exoskeleton, and wandering through it feels like walking through a Dungeons & Dragons map someone forgot to close. This was also our first encounter with the onion domes of Russian Orthodox churches, the locals regarding them like a weed in their distinctly Estonian garden.
Inside of the walls tells a different story; hotels tucked into medieval merchant houses, trendy boutiques, restaurants serving experimental Baltic cuisine, cocktail bars that would feel at home in Berlin. We dropped our bags and made the very conscious decision to abandon all impulses toward restraint. Sometimes you have to be tourists, and Tallinn has no interest in stopping you.
Our first stop was Beer House, a place with a name so direct it almost felt like satire. The interior was a fever dream of antlers, lederhosen, and taxidermied animals posed as if they were mid-shift at a German brewery. A boar held a tray. A wolf towed a wheelbarrow. A squirrel supervised. The wait staff was fully committed to the aesthetic, leaning into the medieval-tavern-cosplay vibe with an enthusiasm that made the whole thing feel delightfully unhinged in the best possible way.
And the pork shoulder. The pork shoulder deserves its own paragraph, because that thing dissolved like it had given up on structural integrity centuries ago. It was tender and salty and fatty in the way camp meals never can be. After weeks of pasta-with-whatever-we-have-left and stovetop improvisations, this was the culinary equivalent of being hugged by someone who knows exactly how you’ve been living.
We wandered further toward a little house tucked into one of Tallinn’s narrow stone alleys, a cocktail bar so small it felt like it had grown there organically, like moss between cobbles. It was packed with tables, alive with the kind of soft hum that only happens when everyone in the room knows they’ve found something special. The owner moved behind the bar with the precision of a craftsman, his partner (who we could only assume was his wife) gliding through the crowd with practiced grace, both of them radiating that unmistakable glow of people living out their dream. The cocktails were wild in the best way: inventive without tipping into gimmickry, beautifully balanced, the kind of drinks that make you pause mid-sip just to process how someone thought them up. Every shelf, every light fixture, every tiny design detail had intention behind it. The place didn’t just serve cocktails; it felt like stepping inside someone’s imagination made real.
Recharged and slightly dazed, we wandered the old town’s alleys until we stumbled into a motorcycle-themed bar that could have been teleported straight out of an American highway. Neon beer signs, chrome details, custom bikes everywhere you looked—some of which had apparently taken home serious awards. Estonia keeps its surprises tucked everywhere
.The next morning was a different sort of thrill. Tay had booked us into an off-road enduro training session with OneLove Enduro, and Scott’s stomach had been quietly vibrating with dread from the moment we arrived. We rolled up on our travel-worn machines; laden with rally towers, soft bags, tools, and all the emotional significance of being our literal homes. Everyone else arrived in crisp hard-enduro gear with lightweight race bikes unloaded from immaculate Sprinter vans. You could practically hear “who invited the overlanders” humming in the air.
To their credit, no one said a word. But the looks were loud.
Our instructor immediately picked up on our… let’s say gentle energy. Before even touching the bikes, we had to explain that yes, we wanted to learn the rough stuff, but no, we could not send our motorcycles cartwheeling into a bog because then we would have to sleep in that bog. Taylor had the opportunity to again flex her therapeutic calm and talk Scott off a ledge of abject panic, all while stretching her bike Sammie’s slightly abbreviated legs. Our instructor nodded with the patience of a man used to coaxing nervous puppies through agility courses, then eased us into the day.
The trails wound through forests that retained night’s dampness even at noon. Mud that wanted your front wheel. Sand that behaved like someone had spilled sugar across the path. Loam that smelled wonderfully ancient. Taylor wound her way through the landscape like the gazelle that truly must be her spirit animal. Once Scott’s bike Katie was stripped all the luggage, she transformed from a lumbering mule into something with teeth. He even managed to keep up—mostly—without providing the forest any new KTM-shaped art installations.
By the end, our boots were caked, our arms were trembling, and our nerves were pleasantly frayed. The kind of tired that feels earned. Our instructor hinted we might cross paths again someday, and we genuinely hope that happens. Riding skills aside, Scott had the kind of calm, competent presence you want around when you’re throwing a motorcycle into terrain it was not emotionally prepared for.
Estonia charmed us without trying; half medieval fantasy, half post-Soviet reality, all wrapped in unexpected generosity and grit. Leaving Tallinn felt like leaving a friend we’d only just gotten to know, and that’s the magic that keeps the road stretching out ahead.