Winter Dispatch: 031
A beginner’s guide to not panicking on your first ski trip.
Today’s letter has been on my list for a long time. Each season I hear from people who want to get into skiing but feel overwhelmed before they even book a flight. The gear! The lingo! The mysteries of the chairlift!
If you’re already a veteran (and most of you trusty readers are), consider this your cue to forward it to the friend who’s been circling the idea of a ski weekend with you for years but hasn’t quite found the courage to say yes.
Chairlift Chatter
Vail Resorts discounted lift tickets by 30% at 12 of its top resorts. You just have to purchase your ticket at least four weeks in advance. Gotta take what we can get at this point.
As of November 1st this year, it’s now illegal to ski in Italy without a helmet. Wonderful!
The North Face x SKIMS collab returns for its second season. Technical outerwear meets signature SKIMS fit and polish. This year’s capsule expands into kidswear and debuts a more refined palette, with new tones like Kyanite and Gunmetal. I really like the cropped puffer. The campaign was shot in the Chilean mountains and also features TOGS writer Kellyn Wilson.
Halfdays launched a collab with Parks Project. Its the brand’s first ever print and is a topographic design of Rocky Mountain National Park. I respect the bold bet here and the colors play very well together. Excited to see this print on the mountain!
A Beginner’s Guide to Not Panicking on Your First Ski Trip
If it feels like all your friends have been skiing since they were basically embryos and you’re over here googling “skiing tutorials,” this one’s for you.
Nothing brings me more joy than hearing someone is taking the plunge on their first ski trip, because the truth is: the hardest part is simply showing up. We celebrate all abilities around here!! Regardless of whether you’re sending it down a double-black or spending forty minutes learning how to walk in ski boots.
Still, getting into skiing can feel a bit like joining a secret society where everyone mysteriously knows the handshake. There’s gear to rent (or buy? or borrow?), mountains to choose, unwritten chairlift etiquette to decode, and that persistent fear of becoming the person yardsaling down the bunny hill while small children effortlessly lap you.
This guide is here to fix that. Think of it as the friend who actually wants to help. Not the one who chirps “just point your skis downhill!” before disappearing onto a double-black while you’re still trying to figure out which foot goes in which boot.
Where to Go
Not all ski resorts are beginner-friendly, and choosing the wrong one is like learning to swim by being thrown into the ocean during a storm. You want mellow terrain, good instructors, and a place that doesn’t make you feel like an imposter in borrowed pants.
East Coast
Okemo (Vermont) - The ideal starter mountain. Long, gentle greens, immaculate grooming, and a layout that won’t trick you into a black by accident. If skiing had training wheels, they’d look like Okemo.
Stratton (Vermont) - Perfect for families. Good variety, cute village, and the kind of mountain where no one is judging.
West Coast
Northstar (Tahoe) - Purpose-built for progression. The beginner area is separated from the chaos of expert skiers flying past you. And the village is walkable + charming.
Rockies
Park City (Utah) - Massive resort, tons of beginner terrain, and the town is five minutes away. Utah snow really is magic – drier, softer, and much kinder to new skiers.
Breckenridge (Colorado) - A sweetheart of a mountain for beginners. And you can walk straight into town when your legs decide they’re done for the day.
Beaver Creek (Colorado) - Rolling groomers, very family-friendly, and fun on-mountain amenities (read: a candy cabin when you need an afternoon sugar high to keep going).
If money isn’t an object: Deer Valley (Utah) - The Ritz-Carlton of ski resorts. Immaculate grooming, limited lift tickets, ski valets, and the calm that comes from a snowboard-free environment (controversial take, but honestly great for beginners).
Skip these for now: Jackson Hole, Crested Butte, Telluride, Alta, Snowbird. Absolutely iconic. Absolutely not where you should learn. Limited beginner terrain!
When to Go (Timing is Everything)
Short answer: January or early March.
Avoid Christmas and Presidents’ Day unless you’re actively studying crowd psychology.
December (pre-holiday): Cheap-ish, unpredictable snow.
Christmas week: Chaos.
January: Sweet spot. Great snow, reasonable crowds.
February: Best conditions, also the busiest. Presidents’ Day is insane.
March: Early March = lovely. Late March = slushy, sunny, extremely fun if you like a softer landing.
The Gear Situation (Do Not Buy Everything)
This is where beginners accidentally light money on fire. Do not buy a full ski setup before you even know if you enjoy this sport.
Rent These
Skis, boots, and poles. Every resort rents them, and local shops are often cheaper. They’ll fit you properly and adjust your bindings so you don’t eject randomly. If your boots hurt, you can swap them (a luxury no purchase offers).
Pro tip: Rent the night before if possible. Don’t burn half of your ski day in a rental line!
Buy These
Real ski socks. Get actual ski socks (Smartwool, Point6, Darn Tough). They’re taller, cushioned in specific zones, and moisture-wicking. Regular cotton socks will bunch up in your boots, give you blisters, and leave your feet cold and clammy. You need 2-3 pairs minimum because you’re going to want fresh ones every day. We don’t subscribe to sock drama around here!!
Base layers. Synthetic or merino wool. Not cotton. Cotton traps moisture and turns into a cold, sweaty disaster. You need a top and bottom base layer that will wick sweat away from your skin. Smartwool, Icebreaker, and Uniqlo Heattech are all solid and not overly $$.
Neck gaiter/buff. Mandatory on windy days.
Good gloves. Do not cheap out here. Your hands will be miserable in $20 gloves. Look for waterproof, insulated gloves.
Rent or Borrow if Possible
Jacket and pants. These are expensive. For your first trip, try to borrow from friends. If you buy, look for sales at REI, Backcountry, or Evo. Make sure they’re actually waterproof (not just water-resistant) and insulated. Scroll through previous Slopeside letters for tons of recos!
Goggles. Some rental packages include these. If buying, get two different lens tints if you can (one for sunny days, one for flat light).
Helmet. Always rentable but when you commit to the sport, make this your first purchase.
What You Can Get Away With
Your regular winter coat and snow pants might work for your first day if the weather’s nice and it’s not snowing. But the second things get wet or windy, you’re going to regret it. Same with warm socks you already own – they’ll work for one day to see if you even like skiing, but after that, invest in the real thing.
Invest in Lessons
Here’s a hard truth: your experienced friend cannot teach you to ski. They learned when they were five, have forgotten the actual mechanics, and will eventually take you somewhere terrifying (I have been guilty of this – allegedly).
Group Lesson: You’re with 4-8 other beginners and an instructor. This is the more budget-friendly option and it’s honestly perfectly fine for your first day.
Private Lesson: 1:1 instruction. You learn faster, get personalized feedback, and can go at your own pace. Absolutely worth it if you can afford it or if you’re going with a partner and can split the cost of a semi-private.
Unwritten Rules You Need to Know
Lift Etiquette!
Fill in all the spots on the chair. You will end up sitting with strangers. This is completely normal. If someone asks “can we join you?” just say yes and shuffle over.
Loading the chair. Wait for the person in front of you to clear the loading zone, then ski or walk into position. Look over your shoulder for the chair coming around. When it hits the back of your legs, sit down. Don’t jump, don’t reach back and grab it, just sit. The chair will catch you.
Safety bar. Once everyone’s seated, someone will likely ask to pull the safety bar down. Don’t be the person who refuses to put it down because you think it makes you look tough.
Unloading. When you see the “unload here” sign, lift the safety bar, put your ski tips up, and push yourself forward off the chair as you reach the ramp. Stand up and ski away from the unloading area immediately so the people behind you don’t crash into you. If you fall right off the lift, get out of the way FAST!
On-Mountain Right of Way
The downhill skier always has the right of way. If someone is below you on the slope, it’s your responsibility to avoid them, not theirs to get out of your way. They can’t see you coming – you can see them.
Look uphill before you enter a trail or merge from the side. Just like merging onto a highway, you need to check that you’re not cutting someone off.
Don’t stop in stupid places. Middle of a narrow cat track? Terrible. Right below a blind rollover where people can’t see you until they’re on top of you? Recipe for disaster. Pull off to the side, out of the flow of traffic.
If you’re stopped and someone crashes near you, always stop. Check if they’re okay and help them gather their gear.
The Green Circle Myth: A green at one mountain can be a blue at another. Trail ratings are relative. Start mellow and work your way up.
Avoiding Common First-Timer Mistakes
Wearing too many layers. You will overheat. Start simple: base layer + mid-layer + jacket.
Skiing until your legs give out. Day one is not the day to test your limits. Leave a little gas in the tank.
Letting your friends drag you onto harder terrain. Their idea of “easy” is not your idea of easy. Split up if needed.
Not drinking enough water. Altitude sneaks up on you!
Skipping sunscreen. Even on cloudy days. Don’t skip this!!
Being too hard on yourself. Everyone looks awkward at first. Everyone falls. Even the best skiers looked like Bambi on ice their first day.
I’ve tried to cover the essentials here, but if I missed anything, plz drop your best tips for the beginner crew!
If you enjoy this letter, please share with friends! Feel free to respond here with ski-related intel, new products you’re loving, or just to say hi. Thanks for reading 💌
Great Stuff - For adults who are beginners, it's best to remember it usually takes 3 ski days of lessons in the same season to go from putting boots on to "skiing." - Its difficult and a bit intimidating for those frist 3 days but suddennly, on the 4th day, it becomes fun and you wonder why you waited so song to try... Don't skimp on the first 3 days...