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Virginia Vineyards and Culinary Delights: 5-Day Middleburg Escape Itinerary

Last updated: 2024 Jun 14

Rolling Hills and Fine Wines

Morning

Begin your Middleburg adventure with a delightful breakfast at Middleburg Common Grounds, where you can savor freshly baked pastries and a cup of locally roasted coffee. Afterward, pick up your electric bikes from Leesburg Full Day or Half Day Electric Bike Rental and enjoy a scenic ride through the picturesque countryside.

Afternoon

For lunch, make your way to Gold Cup Wine Bar at the Salamander Resort & Spa. Indulge in a gourmet meal paired with a selection of local wines. Post-lunch, continue your cycling journey to visit the renowned Virginia Wineries Tours Experience Virginia Wineries and enjoy exclusive tastings at some of the most prestigious vineyards in the region.

Evening

Conclude your day with a sumptuous dinner at The Red Fox Inn & Tavern, one of the oldest inns in America. The historic ambiance and the menu featuring traditional Virginia fare will transport you to a bygone era.

Bedtime

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Leesburg Full Day or Half Day Electric Bike Rental
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5.00
Virginia Wineries Tours Experience Virginia Wineries
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Ashburn Adventures and Culinary Delights

Morning

Start your day with an exciting activity at iFLY Loudoun - Ashburn First Time Flyer Experience. Experience the thrill of indoor skydiving and work up an appetite for a hearty breakfast at Knead Wine, where you can enjoy a farm-to-table meal with a glass of their own wine.

Afternoon

After breakfast, engage in a unique and interactive experience with the Ashburn & Sterling App-Based Murder Mystery Detective Game. Solve puzzles and uncover the secrets of the area. For lunch, head to Lost Barrel Brewing for a laid-back atmosphere and a wide selection of craft beers paired with delicious pub fare.

Evening

Dine at The Bistro at Goodstone, nestled in the heart of the Goodstone Inn & Restaurant. The elegant setting and the farm-inspired menu will provide a perfect end to your day.

Bedtime

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5.00
iFLY Loudoun - Ashburn First Time Flyer Experience
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5.00
Ashburn & Sterling App-Based Murder Mystery Detective Game
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Leesburg Exploration and Evening Elegance

Morning

Take a day trip to nearby Leesburg and enjoy a leisurely breakfast at Market Salamander. Explore the historic downtown area and visit unique shops and boutiques. Don't miss the opportunity to visit the Leesburg Full Day or Half Day Electric Bike Rental and take a ride through the charming countryside.

Afternoon

For lunch, stop at King Street Oyster Bar and indulge in a selection of fresh oysters and other seafood delights. Afterward, continue your exploration of Leesburg or consider a visit to a local winery for a tasting experience.

Evening

Return to Middleburg for a sophisticated dinner at Harrimans Grill, where you can enjoy a menu highlighting the finest local ingredients in a refined setting.

Bedtime

Find amazing hotels in Middleburg.

Leesburg Full Day or Half Day Electric Bike Rental
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Warrenton Wonders and Culinary Surprises

Morning

Venture to the nearby town of Warrenton and enjoy a delightful breakfast at Red Horse Tavern LLC. Explore the town's historic sites and charming atmosphere, then take a morning stroll to work up an appetite.

Afternoon

For lunch, visit Red Bar Sushi and Best Thai Kitchen for a fusion of flavors in a relaxed setting. Afterward, consider visiting a local attraction or taking a scenic drive through the countryside.

Evening

Return to Middleburg for a memorable dinner at CDMX Mexican Bar and Grill, where you can enjoy innovative Mexican cuisine and a vibrant atmosphere.

Bedtime

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Culinary Capstone and Departure Day Delights

Morning

Enjoy a final breakfast at The Restaurant at Goodstone, where you can savor the last tastes of the local cuisine in a serene setting. After breakfast, take a moment to relax and reflect on your trip before preparing for your departure.

Afternoon

For your last meal in Middleburg, visit Tremolo Bar for a unique dining experience. The modern, yet cozy atmosphere and the carefully crafted menu will provide a fitting conclusion to your culinary journey.

Evening

As you bid farewell to Middleburg, reminisce about your favorite moments over a nightcap at Thaiverse Restaurant Middleburg, where you can enjoy a drink and perhaps a small bite to eat before heading to the airport for your journey home.

Bedtime

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