Things To DoThings To Do
Lost Barrel BrewingLost Barrel Brewing
The best place to watch sports, sit by a fire pit, hang out with friends, enjoy the outdoors, drink some beer and grab a bite to eat.
Tremolo BarTremolo Bar
This is the cutest little wine bar that has an unbeatable location, right on main street. You can enjoy a glass of wine or a fun cocktail paired with light bites while you wait on the rest of the wedding guests, friends or family to get into town.
National Sporting Library & MuseumNational Sporting Library & Museum
This is a beautiful museum that focuses on traditional equestrian sports like Fox hunting, shooting, and traditional fishing & hunting focused art pieces. Highly recommend making a stop in for any history buffs wanting to learn more about historic Middleburg or local civil war battles that were fought nearby.
Middleburg Common GroundsMiddleburg Common Grounds
The best place for a morning coffee and a breakfast sandwich. Or enjoy a casual bite to eat for lunch outside on the patio with some friends.
Middleburg MuseumMiddleburg Museum
The Upper CrustThe Upper Crust
This authentic bakery is an institution in Middleburg town. "The Bakery," as everyone locally refers to it, is the best place to grab a sweet treat, sandwiches or a decadent cake or pie. Sophia's favorite cookie is the iced horse shaped sugar cookie, and Alex's is the peanut butter kiss cookie. Don't forget to bring cash!
The Red Fox Inn & TavernThe Red Fox Inn & Tavern
This historic tavern and hotel is a focal point to Middleburg town, and is where multiple Presidents and important historical figures – George Washington, James Maddison, JFK etc. – have stayed at throughout history. The Jennifer & Tony Sirianni had their Rehearsal Dinner here during their wedding weekend in 1991!
Creme de la CremeCreme de la Creme
"Creme de la Creme" is exactly it's translation (the BEST)! This home goods store captures the charm of Middleburg and farm to table life impeccably. It's owned, run and beautifully curated by the Wegdams who are family friends of the Sirianni's. Sophia worked here in high school, and her mom is an avid shopper of the store as well. Highly recommend popping in to get yourself a beautiful candle, vase, or other fun home furnishings over the weekend.
King Street Oyster Bar MiddleburgKing Street Oyster Bar Middleburg
Right on the main street of Middleburg, this is a central place to meet up with friends or pop into after a morning of antiquing or shopping.
Greenhill VineyardsGreenhill Vineyards
Greenhill Vineyards is a true Virginia hunt country vineyard experience. They have a tasting room, light bites, and wine experts who can walk you through their inventory. But the best part of all is the outdoor view of the Blue Ridge Mountains and sloping piedmont valleys. Sophia and her friends made this a fun stop for a party bus tour of vineyards several years ago. Highly recommend for groups wanting to enjoy the countryside!
Hunter's Head TavernHunter's Head Tavern
Quaint and traditional English style pub. This is a bit outside of town (in Upperville), but has great patio seating. The trip outside of Middleburg will allow you to experience the beautiful countryside and iconic Blue Ridge mountains. This is also located next to the church where Alex and Sophia's ceremony will take place.
Boxwood Estate WineryBoxwood Estate Winery
The closest winery to Middleburg town area. Great for groups wanting to do a formal Virginia wine tasting, or just for popping into their taproom and grabbing a glass of wine. This is right across the street from the middle school that Sophia and her sisters attended!
NomadNomad
This is a brewery right in town with good outdoor space and food.
Red Truck Rural Bakery/MarshallRed Truck Rural Bakery/Marshall
This is located in Marshall, the next town over from Middleburg. It's great for baked goods, coffee, and might be located closer to those staying at Airbnb's.
Drive Through the Plains, Marhsll, and RectortownDrive Through the Plains, Marhsll, and Rectortown
Turn-by-turn 50 mins · 13 steps · 3 stops Middleburg -> The Plains -> Marshall -> Rectortown -> Middleburg 1. Drive southeast on South Pendleton Street. 300 ft 2. Turn right onto West Federal Street. 0.1 mi 3. Bear left onto The Plains Road/SR 626. Continue on SR 626. 8.1 mi 4. Turn right onto Main Street/VA 55. 210 ft 5. Stop · The Plains The Plains is on the right. 0 ft 6. Drive northwest on Main Street/VA 55. Continue on VA 55. 4.5 mi 7. Stop · Marshall You have arrived at Marshall. 0 ft 8. Drive northwest on East Main Street/VA 55. 4.4 mi 9. Stop · Rectortown Rectortown is on the right. 0 ft 10. Drive northwest on Rectortown Road/SR 710. 2.4 mi 11. Turn right onto Rokeby Road/SR 623. 3.6 mi 12. Turn right onto Little River Turnpike/US 50. 6.0 mi You have arrived back in Middleburg
Lime Kiln RoadLime Kiln Road
50 mins · 25 steps · Middleburg -> Foxcroft -> Cherry Blossom Farm -> Lime Kiln Road-Middleburg 1. Turn left onto North Madison Street/SR 626. Continue on SR 626. 3.6 mi 2. Turn right onto Foxhound Lane. 0.2 mi 3. Turn right onto Post Lane. 280 ft 4. Foxcroft School Foxcroft School is on the left. 5. Drive south on Post Lane. 0.1 mi 6. Bear left to stay on Post Lane. 80 ft 7. Turn right onto Foxhound Lane. 110 ft 8. Make a sharp right onto Post Lane. 0.2 mi 9. Turn left onto Foxhound Lane. 0.2 mi 10. Turn right onto Foxcroft Road/SR 626. 0.2 mi 11. Turn right onto Mountville Road/SR 745. 0.8 mi 12. Turn right onto Mountville Road/SR 733. 2.2 mi 13. Turn right onto Snickersville Turnpike/SR 734. 0.9 mi 14. Turn left onto Lime Kiln Road/SR 733. 5.7 mi 15. Turn right onto US 15/James Monroe Highway. 530 ft 16. Oatlands 17. Drive south on US 15/James Monroe Highway. 4.5 mi 18. Turn right onto Little River Turnpike/US 50. Continue on US 50. 6.4 mi 23. You have arrived back in Middleburg.