A Local Guide from Kevin & Hilary
Winter in Vail is about more than skiing—it’s about being ready for the day as it unfolds. Some days you ski all morning. Some days, you sneak in two runs between work. Some days you don’t ski at all and just wander the village, coffee in hand. That’s the beauty of it.
If you’re visiting, here’s how we actually do winter in Vail.
What to Pack
Kevin:
Every day in winter, I dress as if I might ski. Even if I’m working all day, I never know when I’ll be able to sneak out for a few laps, so I’m always prepared. I wear ski socks and Patagonia Air long underwear underneath my jeans or pants—it’s flexible, comfortable, and warm without feeling bulky. On top, I’ll wear a really good t-shirt (nice fabric matters) under a cashmere sweater. It looks polished in the store, but it’s warm enough for the mountain or a stop at The 10th.
I’m big on Merino wool beanies—they’re great for skiing and everyday wear. I usually wear my watch under my glove, both for function and style. I always bring a puffy layer, and I never leave home without my Ray-Bans. The sun at altitude is no joke.
I tend to overdress. You can always unzip or shed a layer, but being cold ruins the day fast. I also wear Intuition liners in my ski boots—they’re way warmer and more comfortable. And yes, I usually keep a small flask of Rumple Minze in my pocket for those extra-cold chairlift rides. It’s like an inside hug.
Hilary:
For me, winter packing is about warmth and personality. I always bring a really good sweater, a vintage or statement hat (fur hats are a favorite), great jeans, boots that can handle snow, and a cool scarf. Gloves and beanies are non-negotiable—Craniology makes great ones. Sunglasses are essential, even on snowy days.
Jewelry is a big part of how I pack. I like pieces I can wear the entire trip—I don’t want to be taking jewelry on and off all the time. Chains you never remove, rings that feel comfortable, secure earrings.
When skiing, I wear huggie-style earrings and usually just one pair for the whole trip. I always wear my single stone band skiing, but I’m careful to choose jewelry that won’t snag on gloves—bezel-set, flat styles, nothing with high prongs or big center stones.
One important tip: never check your jewelry. Always keep it in your carry-on, and if you’re skiing, store it safely.
Where to Eat
Kevin:
We go to certain places because of the people. Mountain Standard feels like home—the staff takes great care of us. Same with La Nonna, which is cozy and classic. El Segundo is perfect for big groups; they’re great about letting us use the back room when friends are in town.
For date nights, Hilary loves Asian food, so we go to Matsuhisa or Yama. A midday stop at The 10th is a must—Sasha is the bartender, she’s our neighbor, and her daughter babysits for us. That’s Vail. Small businesses, everyone taking care of each other.
Hilary:
A perfect ski day starts with a burrito from the popcorn wagon and coffee from Two Arrows before hopping on the gondola. Ski a few runs, then stop at The 10th, sit at the bar, say hi to Sasha, make new friends, and order a beer with chili or the wings—they’re really good.
For après, Mountain Standard or El Segundo—get a margarita and tacos.
Yama is a cute small sushi place. I think it's delicious, and our good friends Pat and Gus work there so we like to support our friends.
At Matsuhisa, don’t miss The Gardener cocktail—it’s my favorite!
Where to Shop
Kevin:
Squash Blossom for a trip treat. I also get most of my cashmere sweaters from Graysalt—Zoe always gives great advice. For skincare, Cos Bar is a go-to; Hilary loves all the lotions and creams.
Hilary:
Pano is right across from Squash Blossom—it’s owned by a mother and daughter from Greece, and everything is small-batch. Once it’s gone, it’s gone. Lady Jones has a cool, effortless style—my friend owns it, with locations in Denver and Vail. Alpine Kind is great for gifts, lotions, creams, and they have a hat bar too. If you need kid gifts, Skipper & Scout is adorable and carries Moon Boots.
At Squash Blossom, I love our local charms. Little snowflakes, aspen leaves, and our ski bunny charm—it’s such a sweet Vail souvenir. The ski bunny has a special story: a friend’s grandmother learned to ski here in the 1970s, and her husband bought her a ski bunny charm after she made it down the mountain. We relaunched it last year in her honor. It’s a tiny piece with a lot of heart.
What to Do (Besides Skiing)
If skiing isn’t your thing—or you need a break from the powder—there’s so much else to do. Ice skating at Solaris or Lionshead is always fun. Walk the village, grab coffee, and people-watch.
You can come to Squash Blossom on Mondays and play Mah Jongg. For a more relaxing day, book a massage or facial at the Four Seasons, Gravity Haus (great jacuzzi and sauna), The Lodge (where we’re located), or Manor Vail Spa—Korti does amazing facials and massages.
For music and performances, we love the Vilar Performing Arts Center. Summer has the amphitheater, but winter has its own cozy magic.
Where to Stay
For cozy, vintage Vail vibes, The Christiania is a favorite, and Sarah’s Lounge downstairs is a hidden gem. The Sitzmark is another great intimate option. If you want full resort luxury, the Four Seasons is incredible. The Lodge is also a great choice—right in the heart of Vail and one of the original buildings in the village.
That’s winter in Vail, the way we live it. Layered, familiar, and full of little moments that make the season special. If you’re in town, stop by Squash Blossom— Say hi, have a signature cocktail, and spend a little time with us. Check our events and trunk shows while you’re here; they’re some of our favorite moments of the season!
From Vail, with love,
Kevin & Hilary
