Our family ski trip to Wintergreen

This year we planned a family ski trip to the Wintergreen Resort for MLK weekend in January. We booked our trip in October when the prospects of coronavirus were still very much on the scene. We knew it would be a low-risk activity and were hopeful that Matthew and Molly were at a good age this winter for skiing. It was such a fun getaway and I wanted to share some more details & photos with you here today…

family ski trip

I grew up going to Wintergreen a few times each year. It’s where I learned to ski and one of my best friends from school had a lovely family home in the area. I have such fond memories of my time there and I was excited to share them with David, Matthew, and Molly.

family ski trip

What I LOVE about Wintergreen is the convenience. It is a little under 2 hours away from our house in Richmond so it an easy car ride (even just for a day trip). We booked our house from Saturday – Monday. We didn’t want to push the kids too hard their first time skiing and with the drive being so quick we were able to wake up early on Saturday morning and be on the slopes for their 10:30 am ski lesson.

family ski trip

family ski trip

Where we stayed in Wintergreen:

We rented our home through the Wintergreen resort and landed at a house called The Osprey. Luckily, our house was ready for early check-in when we arrived around 9 am on Saturday morning. This was such a blessing so we could dump our stuff, do a quick bathroom break, and get loaded into our ski outfits before heading back to the resorts.

I would give the accommodations 8/10. It had everything we needed, it was close to the resort and we all slept well. I especially loved the layout – there was an awesome basement with a pool table & lots of space for the kids to run around. We would definitely rent again!

family ski trip

Kids & Skiing

I got a ton of questions on Instagram when I posted about the kids skiing. I wanted to answer all of your questions here in hopes that it will be helpful if you are thinking about taking your kids:

How old are Matthew and Molly?

They were 4.5 years old the first time we took them. I definitely saw younger kids out on the sloops, but in my opinion, this was a great age for it! One needs to be able to balance and have foot control to properly ski. Our daughter picked up on these skills so quickly and I think it’s because she is in ballet class once a week! Our son, who doesn’t, took a little bit longer for it to “click” but he got there on Day 2.

Ski lessons or ski school?

We had heard that it’s good to leave them wanting more after their first time skiing. Ski school wasn’t an option this year anyway so we booked one-hour private lessons for each day we planned to ski. It was a great option! I would highly suggest you coordinate closely with the Treehouse to fill them in on the skill-level of your new skiers. There are two different “bunny hills” and you will definitely want your beginners on the smaller one.

How did they do?

I was so impressed! The first day they did a little bit of skiing after their lesson but they got tired pretty quickly. After their lesson the second day, they didn’t want to stop. We did a few more runs on the bunny hill which was about two more hours of skiing. We opted not to bring them back after lunch in the afternoons and stayed at our rental instead.

family ski trip


  • At this age, private 1-on-1 lessons are the way to go! We made the mistake of putting them together in one lesson (due to coronavirus this made the most sense this year) but the individual attention would definitely have made things better for learning.
  • Rent your equipment before you go. I highly recommend this especially if you have little ones in tow. The lines can be long and lengthy so it helped to skip this step and hit the slopes fresh. Any Richmond locals, you can rent at The Ski Center!
  • Here were a few helpful ski gear items I would suggest besides the obvious: Face mask, wool ski socks, goggles. We rented helmets!
  • You want them as fresh as possible. I would highly recommend starting first thing in the morning when they have the most energy. Try to make the process of getting into their ski gear, getting to the lessons, and onto the mountain as painless as possible. This is what I love about learning at Wintergreen – we could literally get dropped off at the top of the mountain which was a quick walk to the slopes. Snacks are always a must too!

family ski trip

Other Things to Do:

Since Covid was still very much on the scene while we were there, during our hours off the slopes we mostly stayed around our rental house. Luckily, Wintergreen got a big snowstorm while we were there so the kids could enjoy playing outside. It was our first snow of the season! Lots of snowmen, snowball fights, and general excitement. It also happened to be a big football weekend and my family is huge Packer fans. Our rental house had a big TV downstairs where we could watch and enjoy playing games.

family ski trip

family ski trip

However, we very much look forward to going back once coronavirus is passed to enjoy some of Wintergreen’s other activities. Usually, they have activities such as a Kid’s Park with tubing and other snow activities. They also have a larger tubing park for older kids and adults (this is open now). Wintergreen has a nice spa that is open in the winter with a pool and hot tub. Hiking is always an option but we were a little nervous about slippery paths this time. Finally, you can always venture down the mountain into nearby towns. Lots of wineries, restaurants, and breweries are a quick drive. Charlottesville being my favorite!

We can’t wait to go back. Let me know in the comments below if you have any specific questions for me. I’m more than happy to answer!

PS: Check out our other family travels here and here.


  1. Bizzy
    February 5, 2021 / 10:16 pm

    Looks like such a fun trip, and tons of great tips!! Love seeing your beautiful family and all your snowy fun! Thank you Valerie!

    • valeriesmcfarland
      February 6, 2021 / 12:17 am

      Thank you for your comment, Bizzy! We had a great time and can’t wait to go back again soon.

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