How many days do you need in Loudoun County VA?

This itinerary covers 5 days in Loudoun County VA, which is a great amount of time to explore the main highlights. Depending on your pace and interests, you could extend or shorten the trip.

What is the best itinerary for Loudoun County VA?

Plan your perfect 5 days trip to Loudoun County VA. This detailed travel itinerary includes daily activities, local recommendations, and insider tips to make your journey unforgettable.

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.

$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.

$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.

$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.

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.

$50, 2 hours

Find Hotels in Leesburg

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.

$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.

$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.

$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.

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.

$60, 2 hours

Find Hotels in Middleburg

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.

$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.

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.

$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.

$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.

$25, 2 hours

Find Hotels in Purcellville

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.

$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.

$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.

$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.

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.

$40, 2 hours

Find Hotels in Sterling

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.

$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.

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.

$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.

$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.

$50, 2 hours

Find Hotels in Ashburn

Step 1 Outline Preview:

Ultimate Loudoun County VA Exploration

Day 1: Historic Charm

8:00AM

10:00AM

12:30PM

3:00PM

6:00PM

Day 2: Wine & Dine

9:00AM

11:00AM

1:30PM

3:30PM

6:30PM

Day 3: Country Charm

8:30AM

10:00AM

12:30PM

3:00PM

6:00PM

Day 4: Urban Exploration

9:00AM

11:00AM

2:30PM

4:00PM

6:30PM

Day 5: Culinary Delights

8:30AM

10:00AM

12:00PM

3:00PM

6:00PM

Plan Your Loudoun County VA Trip