Middleburg
Day Plans

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

day 1

Exploring the Charm of Middleburg

morning

:

Start your day with a delicious breakfast at a local café. Afterward, stroll through the quaint streets, admiring the historic architecture.

afternoon

:

Visit the local shops and art galleries to find unique souvenirs. Grab a leisurely lunch at a bistro that serves farm-to-table cuisine.

evening

:

Enjoy a wine tasting at one of the nearby vineyards. Conclude your day with a relaxing dinner at a fine dining restaurant.

day 2

Nature's Beauty in Middleburg

morning

:

Hike the trails of nearby state parks, soaking in the fresh air and natural scenery. Don't forget your camera to capture the stunning views.

afternoon

:

Pack a picnic to enjoy by a serene lake or in a scenic park. Afterward, consider renting a bike to explore more of the area.

evening

:

Return to town for a casual dinner at a local pub. Spend some time at a nearby outdoor concert or community event if available.

day 3

Adventure Awaits in Middleburg

morning

:

Rent a bicycle and ride along the scenic countryside roads. Stop at the local farmer’s market to discover fresh produce and crafts.

afternoon

:

Cycle to a nearby vineyard for a guided tour and tasting. Relax in the vineyard’s garden while savoring the wine and beautiful views.

evening

:

Head back to Middleburg to try a local eatery known for its artisanal pizza. Finish your night with a cozy drink by the fireplace at a local pub.

day 4

Artistic Vibes in Middleburg

morning

:

Begin your day at a local art studio for a painting workshop. Immerse yourself in creativity and learn something new.

afternoon

:

Visit art galleries throughout the town to appreciate local talent. Take your time exploring each exhibit and perhaps purchase a piece.

evening

:

Attend a local theater production or live music event. Dine at a farm-to-table restaurant afterward to enjoy fresh, seasonal dishes.

day 5

Equestrian Excursions in Middleburg

morning

:

Visit an equestrian center for a riding lesson or guided trail ride. Experience the beauty of the landscape from a horseback perspective.

afternoon

:

Explore the local history at a nearby museum dedicated to the equestrian culture. Enjoy lunch at a café that specializes in hearty sandwiches.

evening

:

Watch a horse race or practice at a nearby training facility. Cap off the day with a relaxed dinner at a steakhouse renowned for its meat selections.

day 6

Scenic Views of Middleburg

morning

:

Take a sunrise hot air balloon ride to enjoy breathtaking views of the Virginia countryside. Experience the tranquility of the morning sky.

afternoon

:

Have lunch in a charming café with outdoor seating to bask in the afternoon sun. Afterward, visit a local winery for a tour.

evening

:

Enjoy dinner at a rooftop restaurant with panoramic views. Reflect on your day while sipping on a craft cocktail as the sun sets.

day 7

Fall Foliage in Middleburg

morning

:

Begin your day with a walk through local parks known for their stunning autumn colors. Breathe in the crisp air while photographing the scenery.

afternoon

:

Visit local farms for apple picking or a pumpkin patch experience. Indulge in a spiced apple cider as you enjoy fall activities.

evening

:

Attend a harvest festival or seasonal event if available. End your day with a warm meal featuring seasonal ingredients at a local restaurant.

day 8

Shopping Spree in Middleburg

morning

:

Start your day by exploring boutique shops and specialty stores in downtown Middleburg. Find unique gifts and local crafts to take home.

afternoon

:

Stop by a café for a leisurely lunch while you people-watch. Continue shopping at larger retail stores or visiting an antique shop.

evening

:

Share your shopping experiences over dinner with friends at a shared plates restaurant. Enjoy the lively atmosphere of Middleburg’s nightlife.

day 9

Relaxing Retreat in Middleburg

morning

:

Indulge in a spa treatment at a local wellness center for a rejuvenating morning. Enjoy some calm and relaxation before your day kicks off.

afternoon

:

Opt for a leisurely lunch at a café and engage in some light reading or journaling. Afterward, visit a local bookstore to find your next novel.

evening

:

Savor a quiet dinner at a scenic restaurant that offers farm-fresh ingredients. Enjoy a peaceful evening stroll to soak in the peaceful ambiance of the town.

day 10

Wine and Dine in Middleburg

morning

:

Begin the day with brunch at a trendy spot that serves a variety of breakfast dishes. Elevate your experience with local wines.

afternoon

:

Attend a wine tasting tour to sample selections from multiple local vineyards. Learn about the wine-making process during your visit.

evening

:

Enjoy an elegant dinner at a restaurant that pairs food with wines. Wind down with a nightcap as you reflect on the flavors you experienced.

Discover Middleburg

Read more in our Middleburg 2024 Travel Guide.

Middleburg Travel Guide