This winter was our first time ever snowboarding in Virginia. It feels wild to say considering we both grew up in Virginia Beach.

We’ve snowboarded in the Italian Alps, in Breckenridge out West, at Snowshoe West Virginia and Seven Springs, PA… but never in our own home state.

That changed this year, thanks to our now four-year-old.

After a rare snowstorm hit Virginia Beach last January, my husband took him to a giant sand dune near the state park behind our house and let him try snowboarding. That one afternoon turned into a full-blown obsession. We watched snowboarding videos all year. He asked to go constantly. He even had a snowboarding-themed birthday party (I’ll link that post here!).

So this winter we decided to finally explore snowboarding in Virginia, starting with Wintergreen Resort and then Massanutten Resort.

Here’s our full comparison below, especially if you’re planning a family ski trip on the east coast with young kids.

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Wintergreen vs. Massanutten: First Impressions

Wintergreen Resort

We went to Wintergreen for Christmas to have a snowboarding Christmas this year (a white christmas is always fun! and we love an ACTIVE christmas holiday – our 3 year old had been begging to go snowboarding!). Our first impression of Wintergreen is that it is STUNNING, very nice, feels smaller overall, but more like a classic ski resort.

You start at the top of the mountain (which is unique), then ride lifts back up after your runs. The lodge feels cozy and elevated. The views felt slightly more scenic. The food overall pretty good, but you had to drive 30 minutes to the nearest off-resort restaurants or grocery.

We rented a condo that was adorable, updated, and cozy right on the slope via Airbnb and could literally walk out onto the snow. Everything is very close together.

Wintergreen Pros:

• More scenic mountain views
• Classic ski resort atmosphere
• Excellent ski school (we did a private lesson and it was fantastic)
• Better lodge dining overall
• Slopeside condos are incredibly convenient & nice
• Playground at the top of the hill for kids (this was so nice for us with our 1 & 3 year old!)

Wintergreen Cons:

• Smaller bunny slope area
• Less separation between beginners and main runs
• About 30+ minutes to drive to off-resort restaurants or grocery stores

Wintergreen feels:

• More relaxed
• More “out west” in vibe
• More refined and nature-focused

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Massanutten Resort

A few weeks after our visit to Wintergreen, another snowstorm was coming to Virginia so we decided to try out Massanutten nearby instead. It was slightly cheaper and we had already gotten our 3 year old all his own snowboarding gear, so we figured we’d try the other popular Virginia ski resort in the blue ridge mountains. Our first impression was that Massanutten is much much bigger.

There are more lodging options, more terrain parks. More snow production. More activities beyond skiing and snowboarding. You can watch our youtube video showing a fresh powder day on all the terrain parks!

It also feels younger and more energetic, lots of college-aged riders, a lively bar scene, karaoke nights, and a busier vibe.

And for our stage of life? It was actually easier. Let me explain. When we visited Wintergreen, we ONLY focused on our 3 year old learning to snowboard and took turns hanging at the playground or lodge with our 1 year old. Our 3 year old picked up snowboarding in just 2 days! So when we got to Massanutten, I thought, why not let me check if the rentals has equipment small enough for our 1 year old…

Sure enough, they did!! The rental set up was just SO MUCH more convenient at Massanutten because its right NEXT to the bunny slope area (which was wayyy bigger than Wintergreen’s, with multiple magic carpets). I figured let’s just try it out with our 1 year old. I felt we could focus on our 1 year old now since our now 4 year old had picked it up so quickly.

It ended up being so fun, and so much easier to manage both kids on snowboarding learning that we went back to Massanutten 2 weekends in a row.

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Why Massanutten Worked Better for Us With Toddlers

The beginner layout is what made the biggest difference.

Massanutten has:

• Multiple magic carpets
• A large, separated bunny slope area
• Several mini beginner runs
• Rentals that exit directly into the beginner area

That last part is a game changer when you have toddlers.

You rent your gear → walk out the exit → you’re immediately on the bunny slope.

You’re not navigating crowds or hauling kids across busy terrain.

The beginner area is fully separated from main runs, so you’re not trying to teach a three-year-old while experienced riders are flying past.

For families learning to snowboard in Virginia, this layout makes a massive difference.

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Teaching Toddlers to Snowboard (What Actually Worked for Us)

If you’re wondering whether you can teach a one-year-old or three-year-old to snowboard…yes you can! But it looks different than you might think.

Tandem Snowboarding Was Our Secret Weapon

Because our kids are small and light, we did a lot of tandem snowboarding.

We would:

• Ride slowly with them in front of us
• Hold them while making gentle turns
• Walk mini slopes together
• Ride short sections together on the bunny hill

This helped them feel:

• What turning feels like
• How edges engage
• The rhythm of carving

At this age, it’s about feel, not instruction. By the second day, all four of us were snowboarding down the bunny hill together. Core memory unlocked.

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Balance Time Is Just As Important

As helpful as tandem riding was, independent time is critical.

We let them:

• Go down mini runs alone
• Fall
• Wobble
• Figure it out

The large beginner area at Massanutten made this safe and low-pressure.

By day two:

• Our four-year-old was independently riding the magic carpet
• He was going down the bunny hill by himself
• He started learning how to stop and initiate turns

Confidence builds fast when they feel ownership.

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Teaching a 1-Year-Old vs. a 3–4-Year-Old

One-Year-Old

She picked up stance surprisingly fast.

At that age:

• No fear
• No overthinking
• Just instinct

But developmentally there’s a cap:

• Limited endurance
• Limited core strength
• Limited attention span

We kept sessions short — 20–30 minutes max in below-freezing weather.

We used a harness mostly so we could easily grab her — not to hold tension and control speed. Personally, I think leashes work better for skiing than snowboarding. Pulling backward on a snowboard can interfere with natural edge learning.

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Three–Four-Year-Old

He took slightly longer to find balance independently. But because he skateboards, he already understood sideways balance and weight shifting.

Once it clicked:

• He progressed quickly
• Started learning turning
• Practiced stopping

Honestly? Snowboarding felt easier to introduce than riding a bike.

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Terrain Parks & Snow Conditions

If you’re into terrain parks, Massanutten wins.

They have:

• Two larger terrain park sections
• Bigger kickers
• More snowboard-focused features

My husband loved it and would say he prefers the terrain park there. Massanutten also has stronger snowmaking capabilities. On a weekend before a snowstorm hit, they had significantly more open terrain than Wintergreen likely would have in similar conditions. That matters in Virginia.

BUT we LOVED the Wintergreen terrain park with our 3 year old – it was much easier to access and perfect for him to do on his own!

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Food & Lodging: What to Expect

Massanutten Food Review

Ski lodge food? Okay. Expensive.

Ramen shop? Fine.

The waffle stand on the slopes? Incredible. Get the waffle. If you get one thing, get the waffle!

Insider tip:
Right before entering the resort area, there’s a gas station with a Southern-style counter restaurant inside.

Best food of the weekend. Fried chicken, biscuits, green beans. So good.

Also, it’s much easier and closer at Massanutten to drive off resort for additional restaurants compared to Wintergreen!

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Lodging at Wintergreen

Wintergreen had many rentals available right by the slopes, so you had a super short walk to the lifts! We rented a condo on airbnb that was beautiful, cozy, and could see the mountains out our windows! Wintergreen’s slopeside condos are extremely convenient, but you’re more remote from off-resort dining options (30 minutes to the nearest grocery or local restaurants). We didn’t stay in the hotel at all, but in general, the resort is very convenient and everything is close, quaint, and super nice! We loved that we could walk right to the slopes so easily, even with all our gear and the kids.

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Lodging at Massanutten

Our first weekend at Massanutten, we stayed in the hotel closest to the ski resort so we could walk. It was nice and 1 bedroom with a large bathroom and 2 beds. The walk wasn’t exactly super close, but still walkable (just still feels like a lot with a 1 & 4 year old and all our gear). So for our next visit, we booked a condo so we could just drive anyways (farther up the hill a few minutes, but driving was actually easier for us with all the gear and kids) and bring all our own food with a kitchen in the condo and more space to chill/relax.

Hotel Stay at Massanutten

Great for:

• One-night trips
• Convenience

Less ideal for:

• Families of four or more
• Cooking your own food

Condo Stay at Massanutten

Much better for families.

We:

• Booked a condo
• Drove a short distance to slopes
• Brought all our own food
• Had a full kitchen

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Planning Your Virginia Ski Trip: What You Need to Know

Virginia skiing is incredible… when conditions are right.

Timing Around Snowstorms

The absolute best experience is fresh powder. Nothing compares. If you can book when a snowstorm is forecasted, do it.

But here’s the reality: Virginia winter weather is unpredictable. Random warm days can:

• Turn snow slushy
• Create icy conditions
• Reduce open terrain
• Impact how much fun you have

Even with snowmaking, sustained warmth can limit conditions.

For optimal snow:

• Aim for consistent cold temperatures
• Book around snowstorms
• Watch weather forecasts closely

It can feel like a gamble planning far in advance. But when you hit it right? It’s magical. We definitely took advantage that we are a few hours drive from the mountains to time our trips with a snowstorm and fresh powder!

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Approximate Drive Times — Massanutten & Wintergreen

If you’re planning a ski or snowboard trip in Virginia, drive time matters, especially with kids. Here’s a quick look at how long it takes to reach each resort from major cities:

From Richmond, VA

• Massanutten: ~2 hours
• Wintergreen: ~1 hour 45 minutes

From Washington, DC

• Massanutten: ~2.5 hours
• Wintergreen: ~3 hours

From Virginia Beach, VA

• Massanutten: ~3.5–4 hours
• Wintergreen: ~4–4.5 hours

From Raleigh, NC

• Massanutten: ~3.5 hours
• Wintergreen: ~4 hours

From Charlotte, NC

• Massanutten: ~4.5 hours
• Wintergreen: ~5 hours

From New York / New Jersey

• Massanutten: ~5–6 hours
• Wintergreen: ~5–6 hours

From Florida (driving)

• Both resorts are a long drive (12+ hours), so most families flying in will choose nearby airports.

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Best Airports & Rental Car Tips

If you’re flying, here are the most convenient airports for each:

For Massanutten:

• Richmond International Airport (RIC) — typically the closest major option
• Dulles International (IAD) — another solid choice with plenty of rental cars, but it’ll be a much longer drive

For Wintergreen:

• Richmond International Airport (RIC) — also a great option
• Charlottesville Albemarle Airport (CHO) — closer to Wintergreen, but fewer flight options

Be sure to rent a car, both resorts are best accessed with your own wheels, and you’ll want the flexibility to run errands, get groceries, or grab dinner off-resort.

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So… Massanutten or Wintergreen?

Choose Wintergreen if you want:

• Scenic mountain vibes
• Classic ski resort feel
• Excellent ski school
• Cozy slopeside condos

Choose Massanutten if you want:

• Larger beginner area
• Easier layout for toddlers
• Bigger terrain parks
• More snowmaking reliability
• More non-ski activities
• Easier access to restaurants

For us: right now, with a 1-year-old and 4-year-old? We are eager to visit Wintergreen again for how beautiful and nice it was, but Massanutten is easier right now with the bigger bunny slope area and larger terrain park. But we genuinely love both!

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What to Pack for Snowboarding With Kids

It really is going to depend on the weather! When it was below freezing, we had 2 thermal layers and a fleece layer for each kid under their snow overalls + snow jacket! I also found it helped to have knit gloves under the snow mittens for 2 layers on their hands! We only kept them out for 30-60minutes at a time below freezing! At minimum I wanted 2 sets of everything for the kids and us because everything can be wet by the end of the day (which we loved at our condos that we had a dryer to dry the layers at the end of the day!)

For kids:

• Waterproof snow jacket + snow overalls (do the overalls and not the pants!)
• Thermal base layers x 2
• Wool socks (bring extras)
• Winter Hat
• Snow boots
• Waterproof snow mittens (+ extra pair)
• Knit gloves/mittens
• Plenty of snacks!
• Chapstick
• Ski goggles
• Helmet, Snowboard/skis, and snowboard/ski boots (you can always rent at the resort!)

Packing For adults:

• Ski Goggles
• SPF + Chapstick
• Snacks
• Long underwear Thermal layers
• Snowboarding/Ski socks (having proper socks make a HUGE difference!)
• Ski/Snowboard mittens/gloves
• Snow coat
• Snow pants
• UV blocking/UPF layer shirt (for warmer snow days!)
• Fleece vest layer (this is great on a warmer snow day!)
• Fleece jacket layer (SOOO warm for a VERY COLD Day!)
• Neck warmer/face mask (bonus for a kind that magnetizes to your ski googles!! this is crucial for windy cold days)
• Winter hat
• Hand/Toe Warmers (but ONLY for adults!!! kids can’t regulate their temperature the same, so don’t use on your kids!)
• Patience…Lots of patience =)

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Shop it all on my LTK, ShopMy & Amazon Store

You can shop all our snowboarding/ski trip essentials and tested & tried favorites here on my Amazon Store, LTK, and ShopMy!

Kellyyhill’s Amazon Storefront Snow Packing List

Kellyyhill’s LTK

Kellyyhill’s ShopMy

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Final Thoughts

We’ll absolutely be back to snowboarding in Virginia. There’s something special about finding adventure close to home, especially when your kids are this excited about it.

Now we just need to start training… because I have a strong feeling they’re going to outpace us very soon. And honestly? I can’t wait. Now we know we’ll have some more international ski destinations in our future, with how well these closer to home trips went!