Walks with Bear the Dog

and Other Adventures

🌿 Rolling Meadows & Wine Country: A Perfect Mother’s Day in Virginia

Delaplane, VA – Sky Meadows State Park
Rating: ⭐⭐⭐⭐⭐ (Pure Five Paws)

This might honestly be one of the most beautiful Virginia state parks we’ve been to. Rolling Meadows Trail is a true standout — the kind of place that feels more like the English countryside than Northern Virginia.

From the start, the trail opens up into these wide, rolling hills that stretch out in every direction. It’s one of those rare places where everything just feels bigger — the sky, the quiet, even the sense of space around you. The trail also weaves along the tree line for much of the hike, so you get this nice back-and-forth between shaded stretches and open meadow views.

One of the most memorable parts are the old stone walls that run alongside sections of the trail. They feel like little pieces of history just sitting there in the landscape — weathered, simple, and kind of unexpected in the best way. It gives the whole hike a really unique character.

And then there’s the stream — cold, clear, and honestly perfect on a warm day. It’s one of those spots where you don’t really plan to stop long, but end up staying anyway just to cool off for a bit.

Overall, this one has quickly become a family favorite. It’s peaceful, super scenic, and the kind of hike that makes you start thinking about coming back before you’ve even finished it.

👉 Trail link:
Rolling Meadows Trail (AllTrails)

🍷 Post-Hike Stop: Three Foxes Winery & Brewery

After the hike, we headed to Three Foxes Vineyard & Brewery, which was the perfect way to end the day.

We went with white wine for a warm day — crisp, refreshing, and exactly what you want after a long hike in open sun.

For food, we tried a full spread of wood-fired pizzas:

  • Prosciutto, fig, and goat cheese (the standout — sweet, salty, and perfectly balanced)
  • Margherita
  • Bacon chicken ranch

Everything was solid, but that fig and goat cheese combination stole the show.

The covered deck is the real highlight here. It’s spacious, relaxed, and dog-friendly, making it easy to settle in and unwind after the hike.


📍 Trail Stats & Notes

CategoryDetails
TrailRolling Meadows Trail
LocationVirginia
Distance2.5 miles
TerrainRolling hills, meadow paths, wooded edges
Water FeatureCold stream for dipping toes
Dog-FriendlyYes (leashed)
VibeEnglish countryside meets Virginia farmland
HighlightStone walls + endless rolling views

💸 Trip Budget

ItemCost
ParkingFree
HikeFree
Wine~$35
Pizzas (3 total)~$52
Drinks / extras~$3
Total Estimate~$90

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I’m AJ

Mom of three, lover of adventure, and proud human to one very enthusiastic hiking partner – our Aussie – named Bear. Whether we’re exploring a hidden trail in Northern Virginia, wandering along the Potomac, or finding unexpected beauty in a city park, Bear and I are always on the lookout for our next great walk.

This blog is where I’ll share our favorite routes, little discoveries, and the moments of calm (and chaos) that come with hiking alongside a big, curious dog. I’ve always believed the best adventures don’t have to be far from home — sometimes, they’re just a few miles down a new trail.

And while most of these adventures include Bear’s happy paws, every now and then, I’ll post about solo adventures — because sometimes, the best walks are paws optional.

Let’s connect