Weekend guide
48 hours in Middleburg, Virginia
A two-day route built from 4 independent listings on this hub — not a paid ranking.
Saturday afternoon
Settle in outdoors
An easy first pour to get oriented in town.
Winery50 West Winery and Vineyards
Middleburg, Virginia
Saturday night
Stay out for the room
A fuller room and a longer last pour.
WineryBoxwood Estate Winery
Middleburg, Virginia
Sunday midday
Eat with the pour
A calmer second-day stop before you head out.
WineryGreenhill Vineyards
Middleburg, Virginia
Sunday evening
One more round
Close the weekend at a highly rated independent taproom.
CideryMount Defiance Cidery & Distillery
MIDDLEBURG, Virginia
Planning FAQs for Middleburg
How should I spend 48 hours in Middleburg taprooms?
Start at 50 West Winery and Vineyards, then Boxwood Estate Winery, Greenhill Vineyards, Mount Defiance Cidery & Distillery. The route uses 4 independent listings in Middleburg, Virginia.
What is the best dog-friendly taproom in Middleburg?
Taprooms Near Me does not currently flag a dedicated dog-friendly taproom in Middleburg. Check individual brewery pages before you go.
Which breweries in Middleburg have outdoor patios?
Outdoor patio and fire-pit listings are limited for Middleburg right now. Open a brewery profile to confirm seating.
Where are food trucks parked near Middleburg taprooms?
Food-truck rotations are limited in the Middleburg listings right now. Check individual taproom pages for tonight’s lot.