Lindsey Schmidt

Hiking & Wine Tasting with Your Pup in Delaplane, VA

Rummy turned six this month–big day calls for big plans! We wanted an entire day out with her- a park or trail that she’d love exploring, then a winery or brewery for us all to relax in after. We lean towards wineries and breweries because they’re the only places you can order food (or bring your own) and sit indoors with your pup. Her birthday fell on a Tuesday and it was tough finding places open on a Tuesday, before 4pm, that allow dogs inside. But we did and what a great day it turned out to be! We chose Delaplane as it’s an hour and some change West of Alexandria/DC and has two of the most dog-friendly wineries we’ve visited.

Sky Meadows State Park

We started out at Sky Meadows State Park. It was a cool (mid-50s) day, but sunny with blue skies and the perfect day to be outside. There are many trails in Sky Meadows and we chose the James Ball trail at random, which is .83 miles.


It is mostly flat, winding through countryside and Rummy absolutely loved it. You probably won’t completely wear your dog out on this one, but there’s much for them to explore and was a really nice walk for us. We did roughly 35 minutes out then turned back. But the trail continued and there are more that intersect so you can definitely spend a good amount of time here. I’d love to go back when we have more time. The James Ball trail did take us past a picnic area– several large tables covered by a pavilion. So if you’re looking for an afternoon out with a group, this could be a nice place.


They also have a nice gift shop and old farm houses to check out. We didn’t go inside the houses, but it was fun to poke around after our hike.

Naked Mountain Winery

After our “hike”, we headed over to Naked Mountain Winery & Vineyards. We’d been once before and they were incredibly welcoming to Rummy with many tables inside. I’ve said it before but it’s worth repeating– the number of tables inside is so often the determining factor for a visit (with or without a dog). I love wine, but I don’t love it enough to sit outside in early March (or August) to enjoy it. So an abundance of indoor tables is huge and, unfortunately, hard to find. Not exactly an issue in Winter or midweek, but come Summer weekends scoring an indoor table is a sport. Naked Mountain scores in this category. It has a large tasting counter, several barrel “cocktail” tables for two and roughly two dozen tables for four. There’s also a seating area by the fireplace which was very welcoming on this cold day.

Mary greeted us with a warm smile and welcoming attitude. She immediately made us feel comfortable with Rummy and provided not only an informative, but fun, tasting. They offer small bites along with the wine and we chose the pimiento cheese with pita chips which was pretty freaking delicious. I’m a Southern girl (Roll Tide!) so I couldn’t pass it up. It paired very well with the Tannat. No need to worry if pimiento cheese isn’t your thing, they have several other options.

A few photos to reminisce…

The photos below are from a trip out to Naked Mountain during the holidays (looks like we really like their Tannat!). This cheese plate was also great, and Rummy-approved. The photo unfortunately only captures the edge of the fireplace. Definitely worth a visit during the holidays. Can you think of a better way to spend an afternoon than sipping Virginia wine next to a fireplace and Christmas tree with the ones you love (four-legged family members included, of course)? Didn’t think so.

We give Naked Mountain 5 Pups for allowing dogs in the tasting room, plenty of indoor seating and room for several pups without being stacked on each other.

Barrel Oak Winery

The next stop was Barrel Oak Winery. We’ve visited several times as it’s probably the most dog-friendly winery in Virginia. Not only do they allow dogs in the tasting room and have A TON of tables inside, they also regularly support animal rescue organizations. More on that shortly…

As always, Rummy was warmly welcomed at the tasting counter. There were a few other dogs that came in while we were there and Rummy had more than enough room to relax without being crowded by them. There are paintings of dogs all over the tasting room and several of the wines are named after dogs (photo below is their original winery dog), so there is no doubt that your pup is welcome. We even met one of the winemaker’s dogs, Zombie. She’s the sweet shih tzu pictured further down.

Another throwback photo…

Here’s Rummy a few years ago during one of our summer visits. It doesn’t show anything other than the tables are large enough for the kids and dogs to fit under. When it gets crowded, even dogs that are super comfortable in public just want to chill under the table and there’s plenty of room for that here. Another reason we love Barrel Oak.

Regularly Helping Animal Rescues

Outside the main entrance is a sandwich board sign advertising dog gelato and we were happy to meet the woman behind it. Being Rummy’s birthday it was fitting to buy her gelato (as if we need an excuse to spoil her…). While picking flavors, Megan introduced herself as the founder of Martin’s Dog Farm Rescue, a nonprofit specializing in canine rescue, rehabilitation and education.


She started making the gelato out of necessity–to improve the gastrointestinal issues of the dogs she rescued. After speaking with her vet about the gelato, she realized she not only had something the dogs needed, but also something they’d want. So she started selling the gelato to fund more rescues. Rummy is super picky about food and she enjoyed the sweet potato flavor so we were thrilled to support this organization. And we love the fact that dogs can get treats here, too (aside from trying to steal our cheese)!

We give Barrel Oak 5 Pups for allowing dogs in the tasting room, plenty of indoor seating and supporting local animal rescues.

All in all it was a great day. We love wine tasting but also need to include something more active for Rummy. Need to let her burn off some energy before we ask her to mind her manners inside a business. And we got both!

We also took her to on a more challenging hike at Raven Rocks in Bluemont, VA earlier in the week, with a stop at Twin Oaks Tavern Winery after. Be on the lookout for that post coming soon!

Check out our Parks & Walk Routes page for more ideas of where to let your pup explore, and our Wineries page for more places to relax after.