The Ludlow Itch: 72 Hours in Vermont’s Chillest Ski Town
People talk about Vermont like it’s a postcard, all maple syrup and flannel and mountains that look like they were drawn with a crayon. They’re not wrong. But Ludlow? Ludlow is something else. It’s Vermont without the marketing. A town that smells like woodsmoke and tastes like buttered bread. A place where people care more about your boot wax than your Instagram.
If you're angling for a weekend that looks like a snow globe and feels like a fleece-lined secret, Ludlow is the one. Three days, two-and-a-half nights, one fire-lit house. Here’s how to do it.
🛏 Book the Ludlow Hill House before someone cooler than you does. You’ll need a base camp with heat, views, and ideally, a fireplace you can stare into dramatically while sipping tea.
Day One: Out of Office, Into the Snow
5:45 PM – Check into Ludlow Hill House
You’ll arrive just before dark — the ideal time to catch the last light spill over the hills and let your brain start detangling from the week. This house isn’t just a place to crash. It’s a reason to stay in. Quietly luxurious, but not in the sterile-hotel-lobby way. It’s flannel throws, hot drinks, and wide windows that make you question everything about city rent.
7:00 PM – Killarney’s Irish Pub
Every ski town has a “classic local spot,” but Killarney’s earns it. It’s part pub, part town hall, part carb sanctuary. Think Guinness onion soup, shepherd’s pie that sticks to your ribs (in a good way), and bartenders who know how to steer you toward the correct whiskey based on the kind of week you’ve had.
Pro tip: If you're emotionally attached to your fireplace, get your dinner to go and eat it back at the Hill House, where you can let the snow and the steam from your meal blur together in the window reflection.
Day Two: Ski, Drink, Repeat
8:00 AM – Sunrise & Coffee at Home
Let the light wake you up. It hits differently here — sharper, like it’s trying to tell you something. Make a pot of coffee. Ignore your phone. Pretend this is your life now.
9:30 AM – Ski Okemo
There’s a reason everyone mentions Okemo: it’s that good. The slopes are generous, and the snow feels more like a reward than a workout. You don’t need to be an expert — just willing. Whether you're carving hard or watching others do it from the lift, Okemo delivers on the promise of winter.
2:00 PM – Après at Off the Rails
If après-ski is a religion, Off the Rails is where the sermon happens. Expect a little bit of everything — kids in snow pants, seasoned ski dads, couples debriefing their runs over maple sours. Order something fried. Order something local. Do not skip the beer.
Evening – Whatever You Want at Ludlow Hill House
This is the moment the house becomes the main character. You could go out again, but... why? You’ve got leftovers, blankets, and maybe even a board game or two. Pour a drink. Kick your boots off. Let the silence fill your chest like a lungful of snow-dusted air.
Day Three: Slow Exit
9:00 AM – Late Wake-Up, Fire Still Going
The third morning is the heartbreak. It’s the moment you remember this was always temporary. Delay it. Make breakfast. Watch the hills change color outside the windows. Count how many times you’ve said “I could live here.”
11:00 AM – Check-Out (Regretfully)
Packing hurts more when the place felt like a real escape. Leave a note in the guestbook. It’s what you do when a house feels like it was designed with your exact needs in mind.
12:00 PM – Grab Takeout from The Cookster
Don’t skip this part. The Cookster is casual magic — the kind of place that turns “grab and go” into a culinary moment. Sandwiches that travel well. Salads with actual flavor. It’ll keep the weekend going just a little longer, at least until the first toll booth on I-91.
Don’t Call It a Vacation. Call It a Reset.
Ludlow isn’t loud. It isn’t slick. It doesn’t need to be. It’s a pocket of the world where time slows down and meals mean more. Where you can ski like you know what you’re doing, even if you don’t. And where a house like Ludlow Hill House waits quietly, always ready to make the end of the day feel like the real beginning.
Book it. Breathe it in. Come back next season.