Leesburg

Day Trips

Make the most of your day with our curated plans, packed with Leesburg's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Begin your day with a leisurely breakfast at a local café, savoring freshly brewed coffee and pastries. After breakfast, take a stroll through the charming streets of Leesburg's Historic District, admiring the well-preserved 19th-century architecture. Stop by the Thomas Balch Library to learn about the town’s rich history and heritage.

afternoon
:

Enjoy lunch at a farm-to-table restaurant, where you can indulge in seasonal dishes made from locally sourced ingredients. Afterward, visit the Leesburg Corner Premium Outlets for some shopping, where you can find great deals on designer brands. As the afternoon winds down, take a scenic walk along the W&OD Trail, soaking in the natural beauty of the surrounding area.

evening
:

For dinner, head to a cozy bistro that offers a menu of regional cuisine paired with local wines. After your meal, take a leisurely walk through the historic district illuminated by soft evening lights, perhaps stopping at a local ice cream shop for dessert. Conclude your night by catching a live music performance at a nearby venue, immersing yourself in the local culture.

day 2
Wine Tasting in Loudoun Valley
morning
:

Start your day with breakfast at your accommodation or a nearby eatery, fueling up for a day of exploration. After breakfast, drive to the Loudoun Valley, home to some of Virginia's best wineries, and enjoy the scenic countryside views. Your first stop is a picturesque vineyard, where you can join a guided tour to learn about the winemaking process.

afternoon
:

After tasting a selection of wines, enjoy a relaxed lunch at the vineyard's outdoor patio, accompanied by a glass of your favorite vintage. Continue your winery tour by visiting a couple of more vineyards, each offering unique flavors and atmospheres. Don't forget to capture stunning photos of the rolling hills and grapevines that define this beautiful region.

evening
:

Return to Leesburg in the evening and savor a delightful dinner at a local restaurant that features an extensive wine list. After dinner, take a stroll by the Catoctin Creek, where you can listen to the gentle flow of the water and enjoy the tranquility of the setting. If you're in the mood for a nightcap, stop by a nearby brewery for some local craft beer.

day 3
Outdoor Adventure at Morven Park
morning
:

Wake up early and enjoy breakfast before heading to Morven Park, a beautiful estate with sprawling gardens and trails. Spend the morning exploring the park's grounds, taking in the sights of historic buildings and well-maintained landscapes. Consider renting a bike to cover more ground and enjoy the fresh air.

afternoon
:

After a morning of exploration, enjoy a packed picnic lunch on the lush lawns of Morven Park, surrounded by nature. Head to the park's equestrian center for an afternoon of horseback riding lessons or a guided trail ride through the scenic trails. Embrace the spirit of adventure as you connect with these magnificent animals and the beautiful countryside.

evening
:

As the sun sets, return to Leesburg and indulge in a hearty dinner at a local steakhouse that offers a cozy atmosphere. After dinner, take some time to relax at a nearby park or visit one of the local breweries for a casual drink. End your day by enjoying the peaceful ambiance of the town under the starry sky.

day 4
Art and Culture Discovery
morning
:

Start your day with breakfast at a local diner known for its hearty portions and friendly service. Afterward, visit the Loudoun Museum to immerse yourself in the local art scene and learn about the area's history through various exhibits. Take your time exploring each gallery, appreciating the works of local artists and historians.

afternoon
:

For lunch, choose a café that features local art and perhaps even live music. Post-lunch, spend the afternoon at the nearby 868 Estate Vineyard, where you can enjoy art installations and local crafts while sipping on fine wines. Engage with artists and artisans, getting a behind-the-scenes look at their creative process.

evening
:

As evening approaches, head back to Leesburg and dine at a restaurant that specializes in international cuisine. After dinner, attend a local theater performance or art show, immersing yourself in the vibrant cultural scene of the town. Cap off the night with a nightcap at a wine bar, reflecting on the day's artistic discoveries.

day 5
Family Fun at Ida Lee Park
morning
:

Enjoy a hearty breakfast with your family at a family-friendly restaurant before heading to Ida Lee Park. The park features a variety of outdoor activities, so spend the morning enjoying the playground, splash pad, and sports fields. Rent bikes or rollerblades to explore the scenic pathways that wind through the park.

afternoon
:

After a fun-filled morning, have a picnic lunch in one of the park's designated areas, complete with games and laughter. Spend the afternoon at the park's indoor recreational facilities, where the kids can enjoy swimming or participate in organized sports activities. Don't forget to visit the park's community center for any special events or workshops that might be happening.

evening
:

As the day winds down, grab dinner at a casual pizzeria where the whole family can enjoy their favorite toppings. After dinner, take a leisurely stroll around the park or join in on any evening community activities, such as movie nights or concerts in the park. End the day with ice cream from a local shop, creating sweet memories together.

day 6
Historical Landmarks Tour
morning
:

Begin your day with breakfast at a local café, then set off on a self-guided tour of Leesburg's historical landmarks. Visit the Old Courthouse, where you can delve into the town's legal history and admire the stunning architecture. Make sure to take photos at the iconic landmarks such as the Catoctin Creek Bridge.

afternoon
:

For lunch, stop at a historic tavern that offers a glimpse into the past through its old-world charm and traditional fare. Afterward, continue your exploration by visiting the George C. Marshall International Center, where you can learn about the life and legacy of this prominent figure. Engage with exhibits that showcase artifacts and stories from the area’s history.

evening
:

As evening sets in, head to a restaurant that offers a menu inspired by the region's history, perhaps featuring dishes that were popular in the past. After dinner, take a guided ghost tour of the historic district, where you’ll hear spooky tales and legends from the town’s storied past. Conclude your night with a relaxing walk through the town, reflecting on the historical journey you’ve experienced.

day 7
Adventure at Catoctin Mountain Park
morning
:

After breakfast, pack your hiking gear and head to Catoctin Mountain Park for a day of outdoor adventure. Spend the morning hiking one of the scenic trails, taking in breathtaking views of the surrounding landscape. Keep an eye out for wildlife and enjoy the tranquility of nature as you explore the diverse ecosystems.

afternoon
:

Pack a light lunch to enjoy at one of the park's picnic areas, where you can recharge for the afternoon ahead. After lunch, continue your adventure with either more hiking or exploring the park's visitor center to learn about its history and natural features. If you're feeling adventurous, try your hand at rock climbing or bouldering in designated areas.

evening
:

As the sun begins to set, return to Leesburg and treat yourself to a well-deserved dinner at a restaurant that offers hearty meals perfect for hungry adventurers. Share stories of your outdoor experiences over a warm meal, and enjoy a cozy atmosphere. End your day by unwinding at your accommodation, perhaps enjoying a nightcap or planning your next adventure.

day 8
Exploring Local Markets and Festivals
morning
:

Start your morning with a visit to the Leesburg Farmers Market, where you can browse fresh produce, artisanal goods, and local crafts. Enjoy breakfast from one of the food stalls, sampling homemade pastries or breakfast burritos made with local ingredients. Engage with local farmers and vendors, learning about their practices and products.

afternoon
:

After the market, visit a nearby craft fair or festival if one is taking place, immersing yourself in local culture and creativity. Enjoy lunch at one of the food trucks that often appear at these events, offering a variety of delicious options. Spend the afternoon exploring booths, enjoying live music, and participating in any hands-on workshops or activities available.

evening
:

As the sun sets, head to a local brewery or pub for dinner, where you can enjoy unique craft beer paired with pub fare. If there’s a live music event happening in town, make your way there to enjoy the vibrant atmosphere and support local artists. Conclude your day with a leisurely walk through the vibrant streets of Leesburg, reflecting on the day's experiences.

day 9
Relaxation and Spa Day
morning
:

Kick off your day with a nutritious breakfast at your hotel or a nearby health-focused café, preparing for a day of relaxation. After breakfast, head to a local spa for a morning of pampering, where you can indulge in a massage or facial to rejuvenate your mind and body. Spend the morning unwinding and enjoying the tranquil atmosphere of the spa.

afternoon
:

After a morning of relaxation, enjoy a leisurely lunch at a nearby restaurant that focuses on fresh, healthy options. Spend your afternoon at the spa or consider a yoga class at a local studio to continue your wellness journey. If time permits, take a leisurely stroll through a nearby park, enjoying the fresh air and peaceful surroundings.

evening
:

As evening approaches, treat yourself to a gourmet dinner at a fine dining restaurant known for its elegant atmosphere and exquisite menu. After dinner, enjoy a nightcap at a cozy lounge, reflecting on your day of relaxation and rejuvenation. End your evening with a calming walk through the town, soaking in the serene ambiance.

Discover Leesburg

Read more in our Leesburg 2025 Travel Guide.

Leesburg Travel Guide