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By Charles·Holler Guide's AI editor·Trending·

Hunter's Head Tavern: Upperville Hunt Country, Fall 2026

An 18th-century Route 50 tavern in Fauquier hunt country, open Thursday through Monday

Historic stone tavern on Route 50 in Upperville, Virginia hunt country in autumn

Hunter's Head Tavern is an English-style tavern at 9048 John Mosby Highway (Route 50) in Upperville, set in an 18th-century building in the heart of Fauquier hunt country. For an October weekend on the back roads, it is the kind of unfussy table that suits a long lunch or an early supper after a day out.

Quick Facts

  • Where: 9048 John Mosby Highway (Route 50), Upperville, Fauquier County
  • Setting: An 18th-century building, English-style tavern
  • Open: Thursday through Monday; closed Tuesday and Wednesday
  • Google rating: 4.5

Why Upperville in October

Upperville sits squarely in the horse-and-hound landscape that DC-area weekenders already associate with Middleburg, but it reads quieter and more rooted. In autumn the Route 50 corridor is stone walls, turning maples, and pastures worked by people who have been at it for generations. A tavern in a building of this age is a natural fit for the season: the point is the room itself, an 18th-century building that has been part of this stretch of Route 50 for a very long time.

What a Tavern Table Means Here

Hunter's Head is described as serving traditional English-style fare. We don't have a current menu to quote, so treat any specific dish as something to confirm when you call or look at the restaurant's website before you go. What the format promises is straightforward: pub-weight comfort cooking, a proper pour, and a room built for lingering rather than turning tables. Pair it with a fall afternoon and it does what a good tavern should, which is give the day a place to end.

Timing Your Visit

Hours differ across the week, and that matters for planning:

  • Thursday, Sunday and Monday: 11:00 AM to 8:00 PM
  • Friday and Saturday: 11:00 AM to 9:00 PM
  • Tuesday and Wednesday: closed

On a fall weekend in hunt country a call ahead is sensible. If your plans are flexible, a Thursday or Monday lunch fits comfortably within the posted hours.

Building a Fauquier Day Around It

Hunter's Head works best as an anchor rather than a destination you rush to. Pair it with the pastoral drive on Route 50 and a slow afternoon. If you are heading further into farm country, Messick's Farm Market in Bealeton is open daily and is a natural fall stop for produce and farm goods. For a different kind of evening, the stately rooms at Salamander Middleburg sit just across the county line in Loudoun, for guests who want a resort base for the weekend.

Planning Your Visit

  • Address: 9048 John Mosby Highway (Route 50), Upperville, VA
  • Phone: (540) 592-9020
  • Website: huntersheadtavern.com
  • Hours: Monday 11:00 AM to 8:00 PM; Tuesday and Wednesday closed; Thursday 11:00 AM to 8:00 PM; Friday and Saturday 11:00 AM to 9:00 PM; Sunday 11:00 AM to 8:00 PM

We haven't had a recent update from the tavern, so confirm hours and the current menu by phone before making a special trip, particularly on a holiday or event weekend. Find the restaurant's listing at Hunter's Head Tavern.

Places in this story

Sources

Reporting drew on sources available for these places:

  • Hunter's Head Tavern — venue signals
  • Messick's Farm Market — venue signals
  • Salamander Middleburg — venue signals

Frequently asked questions

Where is Hunter's Head Tavern?

Hunter's Head Tavern is at 9048 John Mosby Highway (Route 50) in Upperville, Fauquier County, Virginia.

What are Hunter's Head Tavern's hours?

It is open Monday and Thursday through Sunday, 11:00 AM to 8:00 PM, with Friday and Saturday running until 9:00 PM. It is closed Tuesday and Wednesday.

What kind of food does Hunter's Head Tavern serve?

Hunter's Head is an English-style tavern in an 18th-century building serving traditional fare. Confirm the current menu with the restaurant at (540) 592-9020 or on its website.

Is Hunter's Head Tavern a good stop on a fall weekend in hunt country?

It is a good stop on a Fauquier fall day, since it is open for lunch and supper most of the week. Call ahead on a weekend to confirm hours.

This article was written from local venue data and reviewed by AI. Learn how we write these stories

Photo via Unsplash