A Dog-Friendly Wine Country Weekend for Two.

A weekend where your dog is part of the plan.

Designed especially for couples traveling with a dog, this weekend combines places where pets aren't simply permitted, but can genuinely be part of the day — markets and historic villages, a brewer-led tasting, Virginia wine, alpacas, a tiny country store and a night on a peaceful farm.

Markets, history, craft beer & Virginia wine.

1. 1
   Stop 1

   Start at a Local Farmers Market

   Begin your weekend among local growers, makers and neighbors at a small-town farmers market in the heart of Western Loudoun. Browse seasonal vegetables, herbs, flowers, baked goods and locally made products, pick up something for the road, and get your first taste of the region's thriving agricultural community. It's an easy, relaxed beginning to the weekend — and a chance for both you and your dog to stretch your legs before heading into the countryside.

   
2. 2
   Stop 2

   Explore a Historic Village & Preserved Farm Trail

   Step back in time in a remarkably preserved 18th-century Quaker village, now designated a National Historic Landmark. Take a self-guided walk past historic homes, stone walls and quiet lanes before heading onto a scenic trail through preserved farmland. The combination of history and open countryside makes this an especially lovely stop when traveling with a dog — and provides a glimpse into the agricultural landscape that has shaped Western Loudoun for centuries.

   
3. 3
   Stop 3

   Guided Craft Beer & Food Pairing

   Discover the flavors and stories behind locally crafted beer through a guided tasting led by the brewery's maker. You'll taste four different beers, learn about the ingredients, brewing choices and techniques that give each its distinctive character, and hear directly from the maker about the craft behind what's in your glass. Each beer is paired with a carefully selected bite designed to complement or contrast its flavors, turning the tasting into a delicious exploration of how beer and food can bring out the best in one another. And your dog doesn't have to sit this one out. This is one of the few local breweries that welcomes dogs both inside the taproom and outdoors, giving you the freedom to choose where you'd like to enjoy your tasting — settle in inside together, or head outdoors when the weather is too beautiful to resist.

   Crave Locally Exclusive

   Capture the experience with a special photo opportunity with the makers, arranged exclusively for Crave Locally guests.

   
4. 4
   Stop 4

   Guided Tasting at a Truly Dog-Friendly Estate Winery

   This isn't a winery where dogs are simply allowed — it's a place designed for wine lovers who want to bring their dogs along. Settle in for a guided tasting of locally produced wines at a family-owned estate winery while your four-legged companion enjoys something especially unusual: a dedicated dog park right on the winery property. You can sip your wine while your pup gets a chance to run, play and burn off some energy. It's a perfect example of the difference between “pets permitted” and truly pet-friendly.

   Crave Locally Exclusive

   Your visit includes special coupons exclusively for Crave Locally guests, so you can enjoy savings on purchases during your visit.

   
5. 5
   Stop 5

   Dinner Inside a Historic Grain Mill

   End the day with dinner in a beautifully restored historic grain mill that has been transformed into one of the area's beloved gathering places. The setting connects Western Loudoun's agricultural past with its contemporary food culture, while a pet-friendly outdoor patio means your dog doesn't have to miss dinner. Enjoy a leisurely meal before making the short drive to your countryside accommodation.

   
6. 6
   Overnight

   Stay on a Historic Farm

   Instead of leaving the countryside at the end of the day, stay right in the middle of it. Settle into a charming bed-and-breakfast on a historic working farm surrounded by the quiet landscape of Western Loudoun. The property welcomes guests traveling with dogs and provides a peaceful place to slow down after a full day of exploring. Wake up in the countryside and enjoy a homemade breakfast before beginning Day Two.

   

Farm life, back roads & Blue Ridge views.

1. 6
   Stop 6

   Private Alpaca & Llama Farm Experience

   Start the morning by meeting some of Western Loudoun's most charismatic farm residents. Visit a family-run working farm where alpacas and llamas are raised for their luxurious natural fiber. Get an up-close introduction to the animals while learning about the farm, fiber production and the family behind it. It's a wonderfully personal look at another side of Loudoun agriculture — and at the creative ways small family farms are keeping agricultural traditions alive.

   
2. 7
   Stop 7

   Take the Back Roads to a Historic Country Store

   Now it's time to get a little off the beaten path. Follow scenic country roads through rolling farmland to a tiny rural village and its historic general store — a community gathering place that has served local residents for generations. Browse local goods, pick up a snack or drink, and soak up the atmosphere of a place that still feels connected to an earlier era of rural Virginia. Sometimes the drive really is part of the experience.

   
3. 8
   Stop 8

   Vineyard Tasting with a Blue Ridge View

   Finish your two-day adventure high above the surrounding countryside at a vineyard known for its sweeping views across the Loudoun Valley toward the Blue Ridge Mountains. Settle in for a tasting of Virginia wines that also offers a glimpse into the vineyard's wine club selections. Your dog can join you as you linger over your wine and take in the landscape you've spent the weekend exploring. Time your visit for late afternoon and you may get one final reward: a spectacular Virginia wine-country sunset.

   Crave Locally Exclusive

   Take home a souvenir wine glass as a keepsake from your final stop and your weekend in Virginia wine country.

   

A glimpse of the weekend.