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Upperville

Welcome to Upperville, VA 20184 – a charming gem in the heart of Virginia's horse country! This picturesque village is a delight for travelers, with its stunning equestrian farms, quaint shops, and delightful eateries. Don’t miss the iconic Upperville Colt & Horse Show! Stroll through its historic streets and soak up the countryside charm – it’s pure Americana! 🐎✨

Recommendations

Outdoor4.5/5

Battle of Upperville | Goose Creek Bridge Historic Park

The Battle of Upperville at Goose Creek Bridge Historic Park offers visitors a glimpse into Civil War history, with scenic landscapes and informative markers that bring this pivotal clash to life.

Landmark4.8/5

Upperville Horse Show

Experience the charm of the Upperville Horse Show, an iconic equestrian event showcasing top-tier competition amid scenic Virginia countryside, where tradition and community come together in celebration of horse culture.

Landmark4.5/5

Salem Oaks Farm

Nestled in the scenic Virginia countryside, Salem Oaks Farm offers a charming blend of rustic elegance and breathtaking landscapes, making it a perfect destination for unforgettable gatherings and serene retreats.

Landmark

Old Welbourne Farm and Dulany

Nestled in the scenic Virginia countryside, Old Welbourne Farm and Dulany offer a charming blend of history, stunning landscapes, and iconic architecture, making it an unforgettable destination for nature lovers and history enthusiasts alike.

Landmark4/5

Llangollen Farm Virginia International Polo

Nestled in the picturesque Virginia countryside, Llangollen Farm Virginia International Polo offers thrilling polo matches amid stunning landscapes, making it an iconic destination for sports enthusiasts and a perfect spot for unforgettable social events.

Landmark

Rose Hill Farm

Culture4.8/5

Trinity Episcopal Church

Culture5/5

Upperville United Methodist Church

Culture

Upperville Library

Landmark5/5

Piedmont Fox Hound

Landmark

Salem Course

Landmark

Lazy Lane Farm Inc

Landmark

Heronwood Farm & Golf Course

Landmark4.5/5

Foxlease Farm

Landmark4.6/5

Ayrshire Farm

Eat$$$4.5/5

Hunter's Head Tavern

Eat

Wolf Tones Irish Pub

Cafe4.6/5

Bluewater Kitchen

Eat4.7/5

Upperville Country Store

Eat5/5

Upperville Auto & Deli

Stays

Stay4.7/5

Goodstone Inn & Restaurant

Welcome to Goodstone Inn & Restaurant, a charming countryside oasis nestled amidst the rolling hills of Middleburg, VA. This delightful retreat offers a mix of elegant rooms, picturesque gardens, and delectable farm-to-table dining. Whether you're savoring a gourmet meal or strolling through the scenic estate, Goodstone promises a memorable and whimsical escape from the hustle and bustle of everyday life.

Stay4.65/5

The Ashby Inn & Restaurant

Nestled in the heart of Virginia's wine country, The Ashby Inn & Restaurant offers a charming blend of historic elegance and farm-to-table cuisine, making it a must-visit for food lovers and romantic getaways.

Self Care4.55/5

Salamander Middleburg

Welcome to Salamander Middleburg Resort & Spa, the ultimate oasis for travelers seeking relaxation and adventure. With its charming location in Middleburg, VA, this resort offers countless opportunities to explore the beautiful countryside and indulge in luxurious spa treatments. Take a dip in the pool, savor delicious cuisine, and unwind in elegantly designed rooms. Get ready for a blissful staycation!

Stay4.9/5

Welbourne

Stay4.8/5

The Manor at Airmont

Nestled in the picturesque countryside, The Manor at Airmont offers a stunning backdrop for events, complete with breathtaking views and elegant architecture, making it a perfect destination for unforgettable gatherings and serene escapes.

Stay4.6/5

The Red Fox Inn & Tavern

Nestled in the heart of charming Middleburg, The Red Fox Inn & Tavern is a historic gem offering cozy accommodations, delicious cuisine, and friendly service. Enjoy a stay in a 1728 inn, savor traditional American fare in the tavern, and explore the quaint shops and wineries nearby. A perfect spot for a relaxing getaway!

Stay4.2/5

Foxglove Retreat

Nestled in the serene Blue Ridge Mountains, Foxglove Retreat offers a tranquil escape with stunning views, inviting accommodations, and nature-inspired activities, making it a perfect destination for relaxation and rejuvenation.

Things To Do
Provided by

5/5

6 h

Private Loudoun County Wine Tour from DC with 3 Winery Stops

Let us escort you on a wonderful and relaxing full-day tour through some of the finest wineries in Loudoun County, Virginia. Complimentary hotel pick-up and drop-off is provided from all hotels within the Washington, DC metro area. Along the way, enjoy the natural beauty of the rural landscape on this scenic drive through Loudoun County. The tour includes stops at three popular local wineries, such as Stone Tower Winery, Fabbioli Cellars, and Casanel Vineyards (locations may vary depending on availability), with approximately one hour to enjoy at each destination. This is a private experience for groups of up to 14 passengers, with a total duration of six hours — time that will fly by as you ride in comfort and style in a luxury vehicle. Please note: Wine tastings and tours inside the wineries are not included. Customers are responsible for making their own reservations directly with the wineries. We provide transportation only.

$495.00

5/5

6 h

Northern Virginia Private Custom Wine Tour and Tasting from DC

Please note: This tour doesn't include admission for the Wineries. Price is for a 6 hour SUV transfer, additional fees will be charged if the tour exceeds 6 hours. This is a completely customizable private wine tour. The locations that are shown are just a sample. If you prefer to visit your desired wineries please let us know so we can customize your 6-hour tour accordingly. Some other sample itineraries include the following vineyards: 868 Estate Vineyards and Breaux Vineyards

$995.00

5/5

8 h

Virginia Winery Excursion by Luxury Vehicle Three wineries

Let us take you through the beautiful Virginia countryside in a luxury vehicle as we introduce you various wineries of the old dominion state Nestled in the Northern Virginia heartland acres of vineyards sprinkled with wineries along country roads. We will drive you to a trio of distinct wineries that capture the essence of the mid-south

$1,379.00

5/5

6 h

Harpers Ferry and National Museum of Civil War Medicine Tour

Enjoy a private, full-day historical adventure through West Virginia and Maryland with your own personal driver-guide. Visit the charming town of Harpers Ferry, the Bolivar Heights Battlefield, and the fascinating National Museum of Civil War Medicine. End your journey with a relaxing stroll along Carroll Creek Park in Frederick. Perfect for couples, families, or small groups who want a personalized, comfortable, and flexible travel experience filled with history, culture, and scenic beauty.

$999.00

5/5

Loudoun County 3-Winery Tour from DC Metro or Leesburg

Leave the route planning and driving to us on a relaxed day in Loudoun County wine country. Vineyard Voyages visits three wineries on one of our rotating scheduled routes, with convenient meeting points at West Falls Church Metro or Market Station in Leesburg. A Certified Tourism Ambassador guide hosts the experience while a professional driver handles the road, so you can focus on the scenery, wine, and time together. Each stop brings a different setting and personality, and the day is thoughtfully paced so you have time to taste, explore, and purchase lunch without organizing multiple cars or choosing a designated driver. Choose Explorer for transportation, your guide, and three winery visits while purchasing tastings as you go. Choose Connoisseur for the same hosted experience plus one pre-selected tasting or flight at each of the three wineries. Lunch and additional purchases are separate with both ticket types.

$119.99

4.5/5

Virginia Wineries Guided Tour and Tastings from Washington DC

We pick you up from DC for a day tour of Virginia's wine country where you'll enjoy wine tastings at two different wineries and have lunch (available for purchase at the estate or boxed lunch from us) while admiring the gorgeous views. We will provide history bits, snacks and water, and behind-the-scenes tours and tastings. We will drop you off back in DC before sunset. Join us on a public group tour and meet new friends. What sets us apart: 1. Each winery tour is led by a certified wine expert 2. Guests travel in executive transportation 3. We work with some of the best NOVA wineries and have different routes. 4. We provide light snacks and tastings at two different wineries

$230.00

6 h

Northern Virginia Winery Excursion By Luxury Vehicle 2-Wineries

Let us take you through the beautiful Virginia countryside in a luxury vehicle as we introduce you various wineries of the old dominion state Nestled in the Northern Virginia heartland acres of vineyards sprinkled with wineries along country roads. We will guide you to a duet of distinct wineries that capture the essence of the mid-south

$1,099.00

Exclusive Small Group Virginia Winery Tour with a Sommelier

Embark on an unforgettable Northern Virginia winery tour, led by a certified Sommelier who has extensive knowledge about wines from around the world, and specifically Virginia Wine. The tour will take your group to three exceptional wineries in the region. Relax in a comfortable private vehicle as you explore the picturesque landscapes of the serene Virginia countryside. Enjoy expertly guided tastings, behind-the-scenes experiences, and personalized service tailored to your preferences. Whether you're celebrating a special occasion or simply indulging in a luxurious day of wine exploration, our curated tours offer an unparalleled experience. Discover the finest wines Northern Virginia has to offer with a unique, VIP experience!

$149.00

6 h

Virginia Wine Country Day Trip from DC - Private Luxury Driver

This private, self-guided winery experience gives you the freedom to explore Virginia's renowned wine country on your own terms. Travel in a luxury Mercedes-Benz Sprinter with leather seating, climate control, and ample space — perfect for groups who want comfort and flexibility. Your professional driver handles all the logistics while you enjoy tastings at the wineries of your choice in the Middleburg area. Since winery availability may vary, we customize your itinerary to ensure the best experience on the day of your tour. Flexible pickup from Washington DC, Northern Virginia, and Maryland makes this the easiest and most enjoyable way to discover wine country.

$799.99

3 h 30 mins

Harpers Ferry Private Tour with transportation

Enjoy a private, full-day historical adventure through West Virginia and Maryland. Visit the charming town of Harpers Ferry and the Bolivar Heights Battlefield. Perfect for couples, families, or small groups who want a personalized, comfortable, and flexible travel experience filled with history, culture, and scenic beauty.