Ultimate Loudoun County VA Exploration

Day 1: Historic Charm

Leesburg, Loudoun County VA

8:00AM

Breakfast at Shoe's Cup & Cork

Start your day with a delicious breakfast at Shoe's Cup & Cork, known for its cozy atmosphere and excellent coffee selection.
Head to 17 N King St, Leesburg, VA 20176
$15, 1 hour

10:00AM

Explore Morven Park

Visit the historic Morven Park for a step back in time and a glimpse into the life of Loudoun County's past residents.
Travel to 17195 Southern Planter Ln, Leesburg, VA 20176
$10, 2 hours

12:30PM

Lunch at The Wine Kitchen

Indulge in a farm-to-table meal at The Wine Kitchen offering a picturesque view of downtown Leesburg.
Make your way to 7 S King St, Leesburg, VA 20176
$30, 1.5 hours

3:00PM

Explore Historic Downtown Leesburg

Stroll through the charming streets of Historic Downtown Leesburg, shop for unique finds, and admire the well-preserved architecture.
Enjoy the walk around King St, Market St, and Loudoun St.
Free, 2 hours

6:00PM

Dinner at Tuscarora Mill

End your day with a delightful dinner experience at Tuscarora Mill, known for its upscale Southern cuisine in a historic mill setting.
Head to 203 Harrison St SE, Leesburg, VA 20175
$50, 2 hours
View Hotel Availability

Day 2: Wine & Dine

Middleburg, Loudoun County VA

9:00AM

Breakfast at Market Salamander

Start your day with a gourmet breakfast at Market Salamander, a charming cafe offering delicious pastries and coffee.
Visit 200 W Washington St, Middleburg, VA 20117
$20, 1 hour

11:00AM

Winery Tour at Greenhill Winery & Vineyards

Embark on a guided tour of Greenhill Winery & Vineyards, known for its award-winning wines and beautiful vineyard views.
Travel to 23595 Winery Ln, Middleburg, VA 20117
$25, 2 hours

1:30PM

Lunch at The Red Fox Inn & Tavern

Enjoy a traditional American lunch at The Red Fox Inn & Tavern, an iconic establishment with historic charm and delectable cuisine.
Make your way to 2 E Washington St, Middleburg, VA 20117
$35, 1.5 hours

3:30PM

Explore Middleburg Historic District

Take a leisurely stroll through the Middleburg Historic District, filled with boutique shops, art galleries, and quaint cafes.
Wander around Washington St and Madison St in Middleburg
Free, 2 hours

6:30PM

Dinner at Goodstone Inn & Restaurant

Indulge in a fine dining experience at Goodstone Inn & Restaurant, known for its seasonal menu and elegant ambiance.
Head to 36205 Snake Hill Rd, Middleburg, VA 20117
$60, 2 hours
View Hotel Availability

Day 3: Country Charm

Purcellville, Loudoun County VA

8:30AM

Breakfast at Monk's BBQ

Start your day with a hearty breakfast at Monk's BBQ, known for its delicious southern-style barbecue dishes.
Visit 251 N 21st St, Purcellville, VA 20132
$15, 1 hour

10:00AM

Hike at Franklin Park

Explore the natural beauty of Loudoun County with a hike at Franklin Park, offering scenic trails and peaceful surroundings.
Travel to 17501 Franklin Park Dr, Purcellville, VA 20132
Free, 2 hours

12:30PM

Lunch at Magnolias at the Mill

Enjoy a farm-fresh lunch at Magnolias at the Mill, a popular restaurant known for its innovative American cuisine.
Make your way to 198 N 21st St, Purcellville, VA 20132
$40, 1.5 hours

3:00PM

Visit Doukenie Winery

Experience wine tasting at Doukenie Winery, known for its scenic vineyard views and a selection of exquisite wines.
Head to 14727 Mountain Rd, Purcellville, VA 20132
$20, 1.5 hours

6:00PM

Dinner at Monk's BBQ

End your day with a flavorful dinner at Monk's BBQ, savoring their signature barbecue dishes once more.
Return to 251 N 21st St, Purcellville, VA 20132
$25, 2 hours
View Hotel Availability

Day 4: Urban Exploration

Sterling, Loudoun County VA

9:00AM

Brunch at Eggspectation

Start your day with a delightful brunch at Eggspectation, offering a wide array of breakfast and lunch options to satisfy your cravings.
Visit 21030 Sycolin Rd, Sterling, VA 20165
$25, 1.5 hours

11:00AM

Discover Udvar-Hazy Center

Immerse yourself in aviation history at the Udvar-Hazy Center, part of the Smithsonian National Air and Space Museum, featuring iconic aircraft and space artifacts.
Travel to 14390 Air and Space Museum Pkwy, Chantilly, VA 20151
$20, 3 hours

2:30PM

Lunch at Choolaah Indian BBQ

Enjoy a unique culinary experience at Choolaah Indian BBQ, serving delicious Indian barbecue dishes with a modern twist.
Head to 21426 Epicerie Plaza, Sterling, VA 20164
$20, 1 hour

4:00PM

Shop at Dulles Town Center

Discover a variety of shops and boutiques at Dulles Town Center, perfect for some retail therapy and souvenir hunting.
Explore 21100 Dulles Town Cir, Dulles, VA 20166
Free, 2 hours

6:30PM

Dinner at The All American Steakhouse & Sports Theater

Satisfy your cravings with a hearty dinner at The All American Steakhouse & Sports Theater, known for its juicy steaks and lively sports atmosphere.
Head to 45979 Regal Plaza, Sterling, VA 20165
$40, 2 hours
View Hotel Availability

Day 5: Culinary Delights

Ashburn, Loudoun County VA

8:30AM

Breakfast at Sense of Thai St.

Enjoy a flavorsome breakfast at Sense of Thai St., known for its authentic Thai dishes and cozy ambiance.
Visit 4250D Fairfax Corner Ave, Fairfax, VA 22030
$15, 1 hour

10:00AM

Discover Ashburn's Trailside Park

Explore the scenic Trailside Park in Ashburn, offering walking trails and serene natural surroundings perfect for a morning stroll.
Travel to 20375 Claiborne Pkwy, Ashburn, VA 20147
Free, 1.5 hours

12:00PM

Lunch at Ford's Fish Shack

Savor a seafood feast at Ford's Fish Shack, renowned for its fresh seafood dishes and casual coastal vibes.
Head to 44260 Ice Rink Plaza, Ashburn, VA 20147
$30, 1.5 hours

3:00PM

Visit Lost Rhino Brewing Company

Experience the craft beer scene at Lost Rhino Brewing Company, known for its innovative brews and laid-back brewery atmosphere.
Travel to 21730 Red Rum Dr #142, Ashburn, VA 20147
$10, 2 hours

6:00PM

Dinner at Parallel Wine Bistro

Indulge in a wine-paired dinner at Parallel Wine Bistro, offering a sophisticated dining experience with a curated selection of wines.
Make your way to 43135 Broadlands Center Plaza #121, Ashburn, VA 20148
$50, 2 hours
View Hotel Availability