Arriving at Penny Hedge
We arrived at Penny Hedge on the Saturday morning, dropped the bags in the room, and made a beeline straight for the bar, as you do when you’re finally away for a weekend and the first order of business is to settle in properly. There’s something about that first pint after a journey: you’re still half in “travel mode,” half in “holiday mode,” and the moment the glass hits the table, you can feel yourself shifting firmly into the latter. After a couple of beers, just as we were properly unwinding, our friends turned up. They’d mentioned earlier that they were bringing the dog with them, which I’d happily dismissed as a wind-up. It just didn’t seem likely — not because they aren’t the type to bring a dog to a pub, but because you always assume someone’s exaggerating until they appear at the door with a furry friend trotting beside them. But no, they were serious. They walked in with the dog like it was the most natural thing in the world.
To be fair, the dog was no trouble at all, and I quickly realised it wasn’t going to be the chaos I half-imagined. Every pub we visited across the weekend was completely relaxed about dogs coming in. Nobody batted an eyelid. It’s actually quite refreshing to see how many places in Whitby are dog-friendly; it takes the stress away for people trying to balance a weekend away with not wanting to leave their pets behind. It probably helped that the dog was exceptionally well-behaved — the sort you forget is there until you look down and see two eyes staring hopefully at your crisps.
A Weekend of Pubs, Walks and Whitby Weather
With everyone together, we decided it was time to head into town and get the weekend properly underway. The walk from Penny Hedge into Whitby is a decent stretch, just enough to wake you up and get you ready for another drink. The weather wasn’t on our side — a bit dull, a bit windy, and the occasional drizzle that hangs around without ever committing to a full rain shower — but it didn’t spoil anything. If anything, it added a bit of atmosphere. Whitby suits a moody sky. It goes with the old buildings, the cobbled streets, the harbour, and the history that seems to cling to everything. The kind of place where you half expect a story to emerge from the fog.
We drifted from pub to pub, enjoying the kind of slow afternoon where you lose track of time but don’t really care. The beer went down nicely, the conversation flowed, and the dull weather became background noise. At one point, despite the grey sky and the breeze that made you pull your jacket a bit tighter, we ended up sitting outside eating fish and chips overlooking the harbour. Absolutely determined not to let the typical British weather win. There’s something oddly satisfying about eating fish and chips outdoors, even when the elements aren’t exactly ideal. Maybe it’s the salt in the air, or maybe it’s just tradition, but it felt right.
All in all, the weekend was exactly what we wanted — nothing overly complicated, just good company, good pubs, and a comfortable base to come back to. I’d definitely recommend the Penny Hedge Hotel. It’s well-located, easy to get to, and has the kind of relaxed, friendly atmosphere that makes a short break feel effortless. It did everything it needed to do and did it well.
Things I Learned About Whitby
Aside from the drinking, wandering, and enjoying the place, I picked up a few bits of Whitby history that I hadn’t known before, which added a nice extra layer to the trip. For one, Captain James Cook — yes, that Captain Cook — actually served his apprenticeship in Whitby. He learned the basics of becoming a seaman here, long before he became the explorer everyone knows from school.
Captain Cook’s Whitby Connection
Cook lived in John Walker’s house while training, and that house is now the Captain Cook Memorial Museum. It’s strange to think of someone we usually picture halfway around the world spending some of his formative years walking the same streets and looking out at the same harbour views.
Bram Stoker and Whitby’s Dracula Influence
Another thing I didn’t know was the connection between Whitby and Dracula. Bram Stoker stayed in Whitby in 1890, and the town clearly made an impression on him. When you’re standing by the harbour or looking up at the abbey ruins on the cliffs, it’s easy to see why. The place has a natural drama to it — the gothic architecture, the graveyard overlooking the sea, the steep steps, and the weather that can turn from calm to eerie in minutes. Stoker drew heavily from Whitby’s atmosphere when shaping the setting and mood of Dracula, using the abbey, the coastline, and even local shipwrecks as inspiration. Knowing that while you’re walking around gives the town an extra edge, especially when the sky is brooding and the wind whistles through the lanes. You can almost imagine Stoker jotting down notes as he explored, seeing the story form in front of him.
By the time the weekend came to an end, it felt like we’d crammed a lot in without ever rushing. A good mix of socialising, wandering, eating, drinking, and discovering little bits of history along the way. Whitby has a way of giving you exactly what you need — whether that’s a lively night out, a slow stroll by the harbour, or simply a change of scenery. We left already talking about returning, which is always the sign of a good trip.
Final Thoughts
Looking back, the whole trip had that perfect mix of simplicity and spontaneity that makes a weekend away feel better than planned. Nothing was complicated, nothing was forced, and even the naff weather added a bit of character to it all. Between the pubs, the harbour views, the unexpected history lessons, and the easy atmosphere of the Penny Hedge, Whitby proved to be exactly what we needed. It’s the kind of place you can return to again and again and still find something new tucked away in the streets or perched up on the cliffs. Safe to say, it won’t be our last visit.
Useful Information:
- 🌎 Location: Whitby, a historic seaside town of the North York Moors National Park.
- ℹ️ Details: It has a rich maritime history, including its connection to Captain James Cook.
- ✨ Signature Feature:
- Gothic Heritage: Whitby’s clifftops and ruins provided the primary inspiration for Bram Stoker’s novel, Dracula.
- The 199 Steps: The famous ascent leading from the old town up to the Abbey and St Mary’s Church.
- Local Specialties: World-renowned for its traditional fish & chips, smoked kippers from Fortune’s Smokehouse, and its unique gemstone, Whitby Jet.
- 🏢 Central Landmark: Whitby Abbey.
- 🅿️ Parking: A Park and Ride service is available in peak season.
- 📍 Satnav: Park and Ride.
- 🧭 Coordinates: 54.47983077237942, -0.6534896196177236
- 💬 Access Tip: Purchase tickets for Whitby Abbey online in advance for a discount. For the best views without climbing the 199 steps, access the Abbey via the Headland car park at the top.
- 🌐 Official Link: Whitby Abbey – English Heritage