Lindsey Schmidt

Dog-Friendly Wine Tasting – Charlottesville, VA

What better way to spend a holiday than wine tasting with your dog? We spent a long weekend in search of more dog-friendly wineries in Charlottesville, VA. Planning a trip with a dog always adds an element of difficulty. Summer heat just adds to that as we must find wineries that allow dogs in the tasting room.

We also want to find wineries that are close to each other so we don’t spend all of our time driving, so we enlisted the help of wine blogger Paige Poprocky who we ran into on a wine tasting weekend in Leesburg earlier this year. She posts her favorite winery pics on Instagram and goes into more detail on her blog. We asked her to give us some recommendations for this trip and were thrilled with her picks. You can read her full article here.

With the wineries recommended by Paige, a few we found on our own and a few more we wanted to revisit, we made a really great itinerary. Read on to learn about the dog-friendly wineries in Charlottesville that we visited.

UPDATE 8 July: We rate businesses on our website with a scale of 1-5 pups. These ratings are PURELY based on how easy it is to include your dog. A phenomenal winery may only receive a few pups if they don’t allow dogs in the tasting room and don’t have much shade for them outside. Also, many of these wineries participate in the Virginia Wine Pass, which we’re huge fans of. If you haven’t checked it out, do it. It’s a great way to save money and visit more wineries!

Prince Michel Vineyard & Winery

We started our trip at Prince Michel Vineyard & Winery in Leon, VA. It was right on our route and opens at 10am, which was perfect since we were on the road early. This was a quick stop for us, just the tasting, as it was early. Dogs are allowed in the tasting room, which was great on this already hot day. They have a tasting counter in the large gift shop, so you can look around if you have to wait. We didn’t explore the rest of the building, but did see more indoor spaces outside of the gift shop as well as lawn seating. This was a great stop being right on a main road and allowing dogs inside.

DuCard Vineyards

Next we visited DuCard Vineyards. We’d visited DuCard on a previous trip, but really enjoyed it and had just met the owner at the Mount Vernon Wine Festival (which is truly special–Virginia wine on George Washington’s back yard, overlooking the Potomac… need we say more?). They also allow dogs in the tasting room and have a great patio and grounds to explore.


We were the only ones in the tasting room at this time so Cora gave us an outstanding tasting and tour. As many wineries as we’ve visited, this was actually the first time we’ve taken a tour. She took us to the vineyard and taught us about the grapes and harvesting them; then into the winery to explain the process. Rummy was able to tag along during all of this (nothing actually in production at the time) and she definitely enjoyed being inside on the nice, cool floors while we chatted with Cora.


DuCard has dog-friendly events during the year and are super welcoming to pups every day. Plus there are several tables in the tasting room so your pup can join you in summer and winter. Definitely worth a stop!

Stone Mountain Vineyards

Stone Mountain Vineyards was the next stop and the first of Paige Poprocky’s suggestions. It’s a trek up the mountain (check their website for directions, your GPS WILL lead you astray), but so worth it. Most important, pups are allowed in the tasting room, which is large with lots of seating. Not all wineries have an abundance of indoor seating and it can get packed in summer months, so we really appreciate knowing we have a good chance of scoring an indoor table. Winery dogs Bordeaux and Cabernet greeted us so we immediately felt comfortable with Rummy.


They have a large wrap around deck and another below. The views are really incredible, but we were there during a downpour so we enjoyed our tasting and waited out the rain inside before moving on. This is definitely a place you could spent an entire afternoon, as they have pizzas and other small bites to enjoy with the spectacular view.


This put us near our Airbnb cottage, where we ordered in and enjoyed our Petit Verdot from DuCard. More on the cottage later…

Breakfast, Groceries & A Little Bit of Everything

We chose Free Union because we wanted a home with a yard for Rummy to explore and to be closer to the wineries in the Northwest region of the Monticello Wine Trail. But we hadn’t picked up groceries for breakfast and weren’t returning results when searching for food, so we began the drive closer to Charlottesville to hit a coffee shop.


On the drive out, we passed Wyant’s Store in Crozet and saw their sign advertising hot meals. We’re so glad we stopped as the store has everything you need–a few hot meals made to order as well as a small selection of groceries and other provisions. We hadn’t seen this advertised anywhere and probably wouldn’t have stopped had we not seen the sign for food. If you’re staying in the area, keep this on your radar. Dogs are not allowed inside, but there’s a bench by the door under a covering so she’ll have shade while waiting.

Stinson Vineyards

And lucky for us, it was less than a quarter mile from our first winery of the day, Stinson Vineyards, another of Paige’s picks. They have the loveliest tasting room, just very inviting with fresh flowers, soft colors and lots of sunlight. It is small though, just one table and a small bar seating a total of about a dozen. But dogs are allowed inside and since we were visiting on a weekday, we had the tasting room to ourselves. Pat was a joy to talk to during the tasting and Rummy loved the cool concrete floor. They do have several tables on a completely shaded patio, as well as picnic tables on the lawn. So be prepared to move outside after your tasting, but definitely stop by.

Grace Estate Winery

Just a half mile down the road was our next stop (and another Paige pick), Grace Estate Winery. This was one of the few we visited that does not allow dogs in the tasting room. And while they do have several large tables on the patio and lawn, only a few are completely shaded. They do have umbrellas on the tables, but those can be hit or miss in terms of shade provided, something you can’t really chance with a dog in the hot summer months. We were able to let Rummy sit right outside the tasting room door (in the little shade there was) because we were the only visitors. You wouldn’t be able to do this with crowds, so this is one you can only really visit in the summer with a dog if you’re going midweek during the day.

If you’re wine tasting without your pup, this one is a must see. The tasting room is large with lots of seating and is just really well done aesthetically. It’s obvious this tasting room was built for the customer experience. You’d be very comfortable spending an afternoon there. Random side note, we like the trash can right in the parking lot. It’s always super awkward walking around a winery with a poop bag in hand looking for a trash can. I know I’m not the only one who’s done this walk of shame…

Moss Vineyards

About 15 miles north in White Hall is another Paige Pick, Moss Vineyards. This was one of our favorites. The view is really spectacular and we felt very comfortable. Dogs are allowed in the tasting room. It’s small, just a few tables so only a few can savor the AC. But the floors were nice and cool for Rummy and she racked out during our tasting. Morgan provided one of the most entertaining tastings we’ve experienced. He’s knowledgable for sure, but just as important, he kept us smiling during our tasting. Outside they have Adirondack chairs to enjoy the view, which is exceptional. This one is not to be missed.

Glass House Winery

Another truly unique winery (and the last of our Paige Picks) is Glass House Winery, about four miles south in Free Union. This one has a stunning conservatory and their own line of chocolates. Could we have picked a better place to end our day? Nope. Pups are allowed in the tasting room, which is actually a tasting counter in its own separate space. So enjoy your tasting, then move on to the conservatory which, as the name indicates, is a glass house–floor to ceiling glass windows and a glass ceiling.

There are plenty of tables to sit and relax among the tropical plants. We saw seating for roughly 100 inside, so this is the place to go on a hot day. They have food trucks and stay open until 9:00 on several nights, so this seems like a place that both locals and wine travelers will love. This is one we’ll absolutely visit again.


Then it was back to the house to enjoy our food truck finds at the backyard picnic table. Rummy was so happy to have a yard to roam freely in while we ate and enjoyed the wine we picked up that day. This marks the end of the Northwest Monticello Wine Trail portion of our trip. We stayed in the house another night and wanted to make it down to Charlottesville, but you could absolutely make a trip of just this portion of the trail.

Trump Winery

We started early the next morning at Trump Winery. We arrived when they opened at 10:00 and there was already a line! Dogs are not allowed in the tasting room, but the patio right outside is completely covered and tented (so cooler) with many tables. There are also tasting bars in the tented patio open later in the day, so you can taste outside with your pup. We poured Rummy a bowl of water from the ice water coolers and headed inside for our tasting. In addition to the usual red and white tastings, they offer a separate one for their sparkling wines.

Albemarle Estate

Another extra you’ll find here is the winery’s hotel, Albemarle Estate. We stayed here a few years ago and it was one of the most stunning anchors for a wine tasting weekend we’ve experienced. First class accommodations, customer service, food, everything. And dogs are allowed everywhere but the dining room. Rummy joined us for sparkling in the piano room and pizza by the pool. Without a doubt the nicest place we’ve stayed that is 100% dog friendly. Read about that stay here.

Glenn, the Director of Food & Beverage, was phenomenal during that stay and the reason we ended up renting the theatre room for a double feature. Seriously, check out the private theatre. Bottomless candy and popcorn are exciting for adults, too! Pair it with the Blanc de Blanc and you have yourself a night. We ran into Glenn at the winery on this trip and not only did he remember us, he remembered details of our stay a few years back. Exactly what we’d expect here. If you’re doing a Taste n’ Run (to hit max wineries in this super dense winery region), make sure you grab a glass and head out to the Adirondack chairs on the lawn. The views are just incredible (I’m running out of adjectives for Charlottesville…) and there were at least a half dozen dogs enjoying the lawn with us. Great stop for the pups.

Quick sidebar… there are so many wineries right here there that we would love to have revisited. Blenheim Vineyards and Gabriele Rausse are both within a mile and both great memories from our last trip with Rummy. But this is the Charlottesville “curse”. So much goodness. You have to choose.

Tasting Room & Tap House at Mount Ida Reserve

I visited the Tasting Room & Taphouse at Mount Ida Reserve in November when they had been open for just a few weeks. (Read about it in the recap of my Alabama to Virginia road trip here). This is one of the more stunning views in Charlottesville so it was worth a second visit.

The tasting room is beautiful and one could very comfortably hang out there all afternoon. It’s clear this tasting room was built for the customer experience and does not disappoint. But alas, dogs are not allowed inside. There are quite a few tables outside that are completely shaded (check in at the host stand first). They also have tasting counters outside so we were able to enjoy our tasting with Rummy. Beer is offered as well, but we only tasted the wine.

There are many tables outside (both shaded and on the lawn) with lawn games and lots of things to keep you entertained along with the views. And the food options are more extensive than charcuterie. The menu changes– check out a sample here. But it was a hot day and we wanted to be inside, so we moved on after lunch.

Loving Cup Vineyard & Winery

Loving Cup Vineyard & Winery is just shy of 20 miles from Mount Ida, so it may seem random to have made that detour. But we know they allow dogs in the tasting room and it was really hot, so we went with the sure thing.

*Note to wineries: if you allow dogs inside, advertise it. Include it in your FAQs. People with dogs DO look there and we DO plan our visits based on this. Very few of us (probably only me) actually call to ask if you allow dogs in the tasting room. So if it’s not updated on your site or included at all, we’re probably moving on. Back to Loving Cup…

Loving Cup was really nice. Not a huge a tasting room, maybe three tables inside but they have a separate room with a couch where their winery dog, Riley, was snoozing. I walked in to the room and he slowly opened his eyes, completely unfazed. This is a good thing, in my book. The winery is his domain and he’s clearly comfortable there. He was gentle and sweet and made his rounds in the tasting room on his own time.

While seating indoors is limited, they do have a covered deck that looked really lovely. They also have a special wine, the Dudley Nose Rose, that benefits the Nelson County SPCA with each purchase.

Barboursville Vineyards

We’d wanted to visit Bourboursville Vineyards for a while as they’re a Virginia staple. But on our last Charlottesville trip dogs were not allowed in the tasting room. Virginia law has changed since, so we were thrilled to visit the tasting room with Rummy (this was a HOT day).

Theirs is unique in that you taste like varietals at stations. They are well prepared for the vast crowds that surely descend on this Virginia favorite. The floors are cool and Rummy was comfortable at each station, so we felt completely comfortable. There’s more to the property and the family than we realized, so we really enjoyed the educational portion of this one (as well as the wine, of course).

After our tasting, we made the short drive to the ruins on property. These are the ruins of James Barbour’s home, designed by Thomas Jefferson and destroyed by fire on Christmas Day 1884. There’s a small parking lot at the trail (maybe 20 yards) so you can easily drive to it on a hot day. Don’t worry about baking in the sun. From the parking lot it’s a short walk and you’re there. It was really cool getting to see this on winery property. Only in Virginia 🙂

Honah Lee Vineyard

Next up, Honah Lee Vineyard, part of the Montpelier Wine Trail. Maybe I should’ve known this before going in, but the name comes from Puff the Magic Dragon. The tasting room is small. You may be a able to fit four people at the tasting bar, but dogs are allowed inside, the floors are cool and they have delicious jams to sample and buy. They do have tables outside but it was hot and we were on our way back home, so we shared a tasting, bought some jam and were on our way. They were super helpful, though. Showed us a map of the Monpelier Wine Trail (which is up and coming) and pointed us in the direction of some other dog-friendly tasting rooms.

Chateau MerrillAnne

Chateau MerrillAnne is also on the Montpelier Wine Trail and another great one for dogs. To be clear, we haven’t come across a Montpelier Wine Trail winery that doesn’t allow dogs. They do have a winery cat, as well as some cheeky signage in the parking lot about him.

Dogs are allowed in the tasting room where they have several tables, treats for the pups and some really incredible cheeses for sale. There are a few picnic tables outside to enjoy when the weather is nice.

Hammerstone Cellars

The last stop on this trip was Hammerstone Cellars in Orange, VA. Also part of the Montpelier Wine Trail, they allow dogs in the tasting groom. It’s small, just one table inside. But it worked perfect for us as we waited out a rain storm with the Trivial Pursuit provided at the table. They do have a covered patio with several tables if you want to hang out on a nice day. It was a great last stop of the trip.

Airbnb: Charming Country Cottage

Back to our Airbnb, the Charming Country Cottage, located in Free Union. This is a two-bedroom cottage adjacent to the owner’s home, with it’s own private driveway. We really enjoyed this home. Mark and (Mary) Scott are excellent hosts and provided thoughtful amenities to make for a very comfortable stay. The kitchen is stocked with the essentials–coffee station, condiments, dishes and glassware. They also provide for their four-legged visitors with a dog bed, water and food bowls, extra waste bags and leash. We really loved the low windows upstairs. Rummy could stare out the window all day, watching the world go by. She loved being able to see out of all of the windows without a boost!

The living room has a large TV with a remote that is actually set up to be user friendly. They’ve also labeled everything–outlets, switches, etc so you don’t spend your entire vacation trying to find things.

Outside is a patio table in a large, mostly fenced yard. They did warn us that the yard isn’t fully fenced but Rummy is good and stays within view. She really enjoyed the evenings we spent outside where she could explore the yard and stretch her legs. There are a handful of wineries within a few miles of the cottage, so it’s a great base for exploring the NW portion of the Monticello Wine Trail.

Looking forward to our next trip!

Despite the heat it was a really pleasant trip, filled with great wine, food and views. Charlottesville has so much to offer in terms of all three, we can keep going back and never run out of new places to visit. Just need to start planning our next trip!

For more dog-friendly wineries, visit our Wineries page. Check out the other categories as well and if you’d like your business added, just let us know!