Road Trips from Maryland

Wintergreen, VA Vacation with Kids

Every year we take a fall family vacation to Wintergreen, VA. My husband visited here for many years growing up, and we started coming here with my parents in 2013.

Wintergreen is located in Nelson County, Virginia. It is home to the Blue Ridge mountains, Wintergreen Resort, beautiful hiking trails and (maybe most importantly!) dozens of wineries, breweries, distilleries and cideries.

For us, this trip is full of visits to several wineries and breweries, kid friendly hikes, apple picking, and playing in the nearby rivers and streams. This part of VA is LOADED with kid friendly breweries and wineries and we have so much fun exploring them all. In this post, I’ll share a few of our favorite places to visit in the area, as well as where we like to stop to break up the drive.

On the way – W.O. Riley Park – Woodstock, VA

  • 540 Park Ave, Woodstock, VA 22664
  • From where we live in Central Maryland, it is about a 3.5 hour drive to Wintergreen, VA. We like to stop in Woodstock, VA at W.O. Riley Park since it is a perfect halfway point for us. This is a huge, beautiful park that is extremely well maintained. The playground is wheelchair accessible and includes several slides, climbing structures and swings. There is a natural play kitchen and a water pump to create an outdoor water table. There is also super clean permanent restrooms on site – a road trip pit-stop must! There are also picnic tables around the play ground – we usually grab happy meals at the McDonalds drive through down the street and have lunch here after the girls play.

Where to Stay: Wintergreen Resort

Wintergreen Resort offers a variety of outdoor activities including skiing, snowboarding and snow tubing in the winter. There is also a spa as well as indoor and outdoor pools. In the fall and summer (when we typically visit) there is summer tubing, mini golf, a climbing wall, gem mining, bungee trampoline and more! My kids are still pretty young for most of these activities but definitely something we will check out when they are older! For a full list of activities available at the resort, click here.

Our family typically rents a house in the mountains at Wintergreen Resort. This was the first year we stayed in the valley in the Stoney Creek section of Wintergreen. While we missed the views from up in the mountains, it was much more convenient to get out and about by staying in the valley. My dad enjoyed golfing at Stoney Creek golf course as well!

We find rentals on VRBO or AirBNB. We have stayed in condos and houses of all difference sizes. Our family keeps growing so each year we’ve needed something a little bigger. We go on this trip with my parents and brother so we need a pretty big space to accommodate everyone.

Things to Do

Lake Monocan

  • 239 Camping Ridge Lane, Nellysford, VA
  • Lake Monocan is located in the valley in the Stoney Creek section of Wintergreen It is open for swimming during the summer months, but during the fall it is a great scenic place to bring the kids and let them play in the sand

Spruce Creek Park

  • 800 Rockfish Valley Hwy, Nellysford, VA 22958
  • We love exploring the nature playground at spruce creek park! They have an huge mud kitchen, sand box, tree house, a creek stocked with pots and pans for water play, nature trails, and more! We easily spend a few hours here each trip – its always a huge hit with my kids.

Chile’s Peach Orchard

Chile’s Peach Orchard is a family owned orchard in Crozet, VA. They have PYO peaches, apples, strawberries, blueberries, veggies and flowers (depending on the time of year!) We visit for PYO apples every fall and we love it! They are open daily – we usually arrive when they open at 9 on a weekday. After picking apples, they have a great farm market that sells fresh cider donuts and ice cream. My favorite is their peach soft serve – SO good! If you visit a little later in the day, they also have wine shop where you can purchase virginia wines by the tasting, glass or bottle. They have a huge outdoor seating area with picnic tables and a covered pavilion – they even have live music on some weekends!

Breweries, Wineries, Cideries and Distilleries

Alright – lets cut to the chase. The real reason we love coming down here besides the beautiful scenery, is the plethora of wineries and breweries to explore. Nellysford, VA has got to have one of the highest concentrations of kid friendly breweries/wineries in our area. There are SO many and I’ll try to list all the ones we have visited at the bottom of this post. Here I will focus on sharing our favorites to visit with kids!

Blue Toad Hard Cider

  • 462 Winery Lane Roseland, VA 22967
  • GREAT place to bring kids – wooden train play set and a wooden swing set, picnic tables and an easily accessible stream to play in, large open field, fire pits, beautiful views, live music on weekends. Light food/snacks served here – outside food is welcome!

Bold Rock Hard Cider – Nellysford Cidery

  • 1020 Rockfish Valley Hwy, Nellysford, VA 22958
  • TONS of open space to run, events like live music, outdoor movie nights, etc. River runs along the back of the property (though there are very few spots for kids to actually access it to play) Indoor seating, outdoor seating on the deck or tons of spread out picnic tables in the field and along the river. They serve small bites and casual lunch and dinner options (burgers, sandwiches, etc.) Outside food is allowed in the meadow.

King Family Vineyards

  • 6550 Roseland Farm, Crozet, VA 22932
  • Patio with seating, or bring your own chairs/blankets spread out in the field. Sweeping views of the Blue Ridge mountains. Polo pitch on site with matches held on some weekends. Horse stalls where kids can go up and see the horses and a corn operated ride-on horse out front. 5 minutes away from Chile’s Orchard so this is a great spot to visit after apple or peach picking! We also love that it opens earlier than many other wineries – 10 am! Outside food is welcome.

Veritas Winery and Vineyards

  • 151 Veritas Ln, Afton, VA 22920
  • They offer reserved seating indoors or on the patio, or open seating on the lawn (our preference with kids!) THere are picnic tables available or bring your own chairs/blankets. Outside food welcome in the lawn area so we pack a cooler!

Afton Mountain Vineyards

  • 234 Vineyard Ln, Afton, VA 22920
  • Beautiful views, indoor and outdoor seating – both patio seating and picnic tables in a field. Outside food is welcome!

Wild Wolf Brewery

  • 2461 Rockfish Valley Hwy, Nellysford, VA 22958
  • Wild Wolf is a full service brewery AND restaurant. While it doesn’t have as much space to run around as some of the other breweries, it is very kid friendly! There is tons of outdoor seating, a small play area for kids and a koi pond. We really love their beer AND their nachos!

Brewing Tree

  • 9278 Rockfish Valley Hwy, Afton, VA 22920
  • This spot is a new favorite for us! We’ve driven by in the past but it didn’t appear to have a ton of space for the kids to run around so we have previously skipped it – boy were we wrong! Behind the building there is a HUGE sandbox stocked with tons of toys and a mud kitchen. Down the hill is “the meadow”, a wide open field with hammocks, picnic tables, and an easily accessible river that runs along the back of the property. We started off sitting on the patio while the girls played in the sandbox, then headed down to the meadow so the girls could run around and wade in the river. We spent over 3 hours here! The only downside is they do not allow outside food, but they have a “Scratch Kitchen” out front with lunch and dinner options.

Where to Eat

In addition to Wild Wolf Brewery, we also like to eat at the following restaurants.

Paulie’s Pig Out

  • 7376 Rockfish Valley Hwy, Afton, VA 22920
  • Paulie’s is our favorite BBQ place EVER. It is always our first stop when we get into town. Sadly on this most recent trip we arrived to find out it was closed for the week. But when its open, we love the pulled pork, mac and cheese and coleslaw.

Margaritas Mexican Restaurant

  • 2815 Rockfish Valley Hwy, Nellysford, VA 22958
  • Excellent Mexican food – our favorite is the green chili with refried beans and rice. Indoor seating or carry out.

Other great spots to visit in Nelson County

There are so many great places in this area, it’s impossible for us to see them all. Here are some spots we have visited in the past and loved – just didn’t make it this time around:

  • Devil’s Backbone Brewing Company
  • Pollack Vineyards
  • Valley Road Vineyards
  • Blue Mountain Brewery
  • Bryant’s Cider
  • Silverback Distillery

Time to plan your trip!

I hope this summary of our trip inspired you to plan a trip to Nelson County, VA. It is one of our favorite places and one we look forward to visiting every year!

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