A Weekend in Virginia Hunt Country

Nestled among the rolling hills of Virginia’s Piedmont, Hunt Country is known for its timeless beauty, historic charm, and vineyard-lined countryside. We hope you will take time throughout the weekend to explore, relax, and enjoy the landscape that made us fall in love with this special place.

Below, we’ve shared a few of our favorite restaurants, cafés, wineries, breweries, and destinations throughout the area. We encourage you to wander, discover, and savor all that Virginia wine country has to offer.

Middleburg, Virginia

Highly recommend coming here, no matter where you are staying! Elegant, understated, and rich in equestrian tradition, Middleburg is considered the heart of Virginia Hunt Country.

Spend the afternoon strolling through boutiques and art galleries, or visit the National Sporting Library & Museum for a glimpse into the region’s storied heritage. The surrounding countryside is home to some of Virginia’s most beautiful wineries—perfect for a leisurely afternoon among the vines.

Where to Eat & Drink

    • The Bistro at Goodstone Inn — Elegant countryside dining at Goodstone Inn, featuring seasonal, farm-to-table cuisine in a beautiful estate setting. A great choice for a romantic or special-occasion meal.

    • Red Horse Tavern — A casual, lively local tavern serving classic American and pub fare, burgers, beer, wine, and cocktails. Great for an easygoing lunch, dinner, or drinks.

    • Tremolo Bar — A modern wine bar with elevated small plates, creative cocktails, premium coffee, and an impressive wine selection. Refined but relaxed, and perfect for drinks or a light meal.

    • Goodstone Inn & Restaurant — A luxurious countryside inn set on a picturesque 265-acre estate, offering boutique accommodations and sophisticated farm-to-table dining. Ideal for a romantic getaway or special dinner.

    • The Red Fox Inn & Tavern — A historic Middleburg landmark with an intimate dining room and cozy pub. Known for seasonal Virginia cuisine, game and seafood, wine, cocktails, and classic Hunt Country charm.

    • King Street Oyster Bar — A lively seafood spot specializing in oysters, fresh seafood, cocktails, and happy hour. A fun choice for a casual meal or drinks in the heart of Middleburg.

    • Gold Cup Wine Bar at Salamander Resort — An upscale yet relaxed wine bar at Salamander Middleburg, offering Virginia wines, cocktails, and all-day dining in a sophisticated resort setting. Live piano music is featured on Friday and Saturday evenings.

Coffee & Breakfast

  • Cuppa Giddy Up

  • Middleburg Common Grounds

  • The Upper Crust

The Plains, Virginia

Quiet, scenic, and effortlessly charming, The Plains is best experienced at a slower pace.

Enjoy a relaxed morning with coffee and pastries, browse local antique shops, or take a scenic drive past horse farms, stone fences, and open countryside. It is the perfect place to pause and take in the beauty of the region.

Favorites

    • Bistro @ The Porch — A cozy Virginia wine-country bistro offering locally sourced dishes, creative cocktails, and a curated wine list. Great for a relaxed lunch, dinner, or drinks.

    • Girasole (Welcome Party location) — An elegant, chef-owned Italian restaurant known for authentic regional Italian cuisine, fresh pasta, seasonal ingredients, and an intimate European atmosphere. A lovely spot for a special dinner or celebration.

    • The Rail Stop Restaurant — A longtime local favorite offering upscale American cuisine with fresh, locally sourced ingredients. Known for its house-made breads, pastas, and desserts, plus lunch, dinner, and Sunday brunch.

    • The Plains Market — A convenient local market and deli that’s especially popular for breakfast and casual lunch. A good stop for grab-and-go food, deli favorites, and everyday essentials.

Marshall, Virginia

Just beyond Middleburg, Marshall offers a quieter and more understated charm, filled with hidden gems and local favorites. It is the kind of town best discovered slowly—where a simple outing can turn into an unexpectedly perfect afternoon.

Where to Visit

    • Field & Main Restaurant — Upscale yet relaxed farm-to-table dining in a historic home, with seasonal dishes, great wine and cocktails, and a cozy, intimate atmosphere. Great for a special dinner or date night. Would recommend for dinner!

    • The Whole Ox — A local butcher shop and gourmet market with a casual lunch counter, known for high-quality local meats, burgers, fried chicken sandwiches, and specialty provisions.

    • Red Truck Bakery — A beloved Virginia bakery and café serving homemade pies, cakes, pastries, breads, coffee, and sandwiches. A perfect stop for breakfast, a sweet treat, or coffee.

    • Marshall Diner — A classic, no-frills local diner serving traditional American comfort food, with breakfast as a standout. A good choice for a casual, affordable meal.

Warrenton, Virginia

A classic Virginia town with historic character and a walkable downtown, Warrenton offers the perfect blend of small-town charm and local history.

Spend the morning wandering through Old Town’s brick sidewalks, antique shops, and cafés. For those interested in history, the Fauquier History Museum at the Old Jail is well worth a visit. Just outside town, Sky Meadows State Park offers scenic trails, open fields, and sweeping views of the Blue Ridge Mountains.

Where to Eat & Drink

    • Claire’s at the Depot — Casual- elegant dining in a historic train depot, serving American dishes with Southern and global influences, plus cocktails, beer, and wine. Would recommend for dinner out of all other options!

    • Molly’s Irish Pub — A lively Old Town Irish pub with classic bar food, plenty of beer and drinks, and live music. Open later than many spots in town (any spots in town), especially on weekends.

    • Red Truck Bakery — A beloved local bakery and café known for fresh pies, cakes, pastries, breads, coffee, and breakfast/lunch favorites.

    • Great Harvest Bread Co. — A cozy bakery café specializing in freshly baked breads, pastries, breakfast sandwiches, coffee, and casual lunch options.

    • Denim & Pearls — A stylish Modern American restaurant and bar in the heart of Old Town, offering brunch, dinner, cocktails, and a fun atmosphere.

    • Deja Brew Cafe — A cozy coffeehouse and café serving coffee, breakfast and lunch, with beer, wine, and cocktails for a relaxed day hangout.

    • Black Bear Bistro & Brick Oven — A casual neighborhood restaurant known for comfort food, brick-oven dishes, burgers, and a relaxed atmosphere.

    • The Natural Marketplace — A charming natural-foods and wellness shop with organic groceries, health products, and a small upstairs café serving fresh, wholesome lunch options. (Caitlin worked here all throughout high school— her favorite spot for healthy eats!)

Wineries, Breweries & Distilleries

Virginia Hunt Country is home to more than 20 wineries within a short drive, making it one of the premier wine regions in the state.

Nearby Wineries

  • Boxwood Estate Winery

  • Greenhill Vineyards

  • Cana Vineyards

Breweries & Distilleries

  • Lost Barrel Brewing

  • Barrel Oak Winery & Brewery

  • Mt. Defiance Cidery & Distillery

  • The Farm Brewery at Broad Run

  • Old Bust Head Brewing Company

  • Trouvaille Brewing Company

  • Great Mane Brewery

  • Lark Brewing Co.

Additional Destinations

If you plan to extend your stay or explore farther afield, we also recommend:

  • Charlottesville

  • Washington, D.C.

  • Leesburg

  • Culpeper