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Upperville

Upperville is a village in the United States.

Recommendations

Landmark4.5/5

Battle of Upperville | Goose Creek Bridge Historic Park

A historic stone bridge crosses Goose Creek at this park, and a short path lets you walk out onto it.

Landmark4.8/5

Upperville Horse Show

Broad views open across the jumper rings at this Virginia horse-show venue. The hunter side has classic arenas beneath oak trees. Its annual show is America’s oldest, dating to 1853.

Landmark4.5/5

Salem Oaks Farm

Farm in Marshall, Virginia.

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

Polo grounds in Upperville, Virginia.

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

Nestled in the picturesque landscapes of Upperville, VA, Lazy Lane Farm Inc is celebrated for its scenic horse trails and charming rustic ambiance, inviting visitors to experience the beauty of Virginia’s countryside.

Landmark

Heronwood

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

Goodstone Inn & Restaurant in Middleburg offers adults-only rooms with private bathrooms, balconies, and garden or mountain views. Each room includes air-conditioning, a work desk, and free WiFi. The family-friendly restaurant serves American cuisine with vegetarian, gluten-free, and dairy-free options. Breakfast includes champagne, fresh pastries, and a variety of dishes. Dinner features brunch, lunch, and dinner, complemented by a bar. Guests can relax by the seasonal outdoor swimming pool with a view, hot tub, and outdoor fireplace. Additional amenities include a lounge, picnic area, and bicycle parking. Located 28 km from Washington Dulles International Airport, the inn is near attractions such as Chrysalis Vineyards (14 km) and Dulles Expo Conference Center (35 km). Activities include fishing, canoeing, hiking, and cycling.

Stay4.9/5

Welbourne

Stay4.8/5

The Manor at Airmont

This Round Hill wedding venue handles lodging, catering, and planning, turning couples’ mood boards into the design for the day.

Stay4.7/5

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.

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!

Stay4.5/5

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!

Stay4.2/5

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

Antietam Battlefield & Civil War Medicine Museum Private Tour

Experience the American Civil War from two fascinating perspectives in one unforgettable tour! Explore Antietam National Battlefield, site of the bloodiest single-day battle in American history, with a comfortable caravan-style tour. Travel by vehicle between key historic locations, making stops to explore and learn without the need for extensive walking, making this experience enjoyable and less physically demanding. A 30-minute historical film brings the battle’s dramatic events to life. Continue your journey at the National Museum of Civil War Medicine in historic Frederick, where authentic artifacts, surgical instruments, and engaging exhibits reveal how wounded soldiers were treated. What makes this tour special is its unique combination of battlefield history, medical discoveries, and a relaxed, thoughtfully paced experience that brings the human stories of the Civil War to life.

$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 & Bolivar Heights: 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.

$699.00

6 h

Sunday Funday Loudoun 2 Winery Tour from DC Metro or Leesburg

Sunday Funday is our shorter, relaxed Sunday trip to Loudoun County wine country. Sleep in, meet the bus late morning, and spend the afternoon at two Loudoun County wineries while a professional driver handles the road and a Certified Tourism Ambassador host handles the timing. Board at West Falls Church Metro (11:00 AM) or Market Station in Leesburg (11:55 AM) and return to the same spot, about 4:15 PM in Leesburg or 5:00 PM at the Metro. The winery pair changes by date. Your first winery is also your lunch stop, so plan to buy lunch from its menu. Sunday Explorer covers the bus, your host and two winery visits, and you buy tastings as you go. Sunday Connoisseur adds a pre-arranged tasting or flight at both wineries. Lunch is not included with either ticket. Sunday Funday guests may bring up to 2 canned alcoholic drinks per person for the bus. Cans only: no beer, glass or coolers. Solo travelers are welcome, and all guests must be 21 or older.