Hunter's Head Tavern
Upperville
Restaurant in Upperville, United States
Book with PearlThe Read
Dress
Casual
Why go
Book Hunter's Head Tavern when the priority is a relaxed Upperville meal with low ceremony, not a destination tasting-menu night. It is better for lunch, early dinner, families, casual celebrations than for a polished special occasion; cross-shop Goodstone Inn or Harrimans Grill if the meal needs more formality.
About Hunter's Head Tavern
For a low-pressure meal in Upperville, Hunter's Head Tavern is best framed as a casual option rather than a high-expectation destination dinner. Hunter's Head Tavern is in Upperville, has a casual dress code, its posted hours run from late morning into evening on the days it is open.
Plan around the schedule before building the occasion around the meal. Hunter's Head Tavern is open Monday, Thursday, Sunday from 11 AM to 8 PM, Friday and Saturday from 11 AM to 9 PM. It is closed Tuesday and Wednesday.
A tavern choice for casual celebrations, not a trophy meal
The strongest case for choosing Hunter's Head Tavern is when the plan calls for an easy Upperville meal with a casual dress code. It does not feature an awards profile, chef-led format, tasting-menu positioning, price point, or detailed seating information that might serve as a stronger draw, so expectations should stay grounded.
For a relaxed occasion, treat it as a practical dining choice rather than a formal special-occasion room. If the event needs a more polished setting, compare it with nearby options before committing; if the priority is ease in Upperville during the posted hours, Hunter's Head Tavern remains the direct pick.
Use it as the easy Upperville option, then cross-shop for polish
Compared with more occasion-oriented choices in the broader area, this is the low-friction option. Readers planning a more formal meal should also check Goodstone Inn or Harrimans Grill. For something lighter and more casual, Side Saddle Cafe belongs on the same shortlist.
Use our full Upperville restaurants guide if the decision is still open, especially for comparing Hunter's Head Tavern with other dining options. If the meal is part of a larger visit, our Upperville hotels guide, bars guide, wineries guide, experiences guide can help shape the rest of the plan.
Planning details
- Location
- 9048 John S Mosby Hwy, Upperville, VA 20184
- Reservations
- Book on Tock
- Website
- huntersheadtavern.com
- Phone
- +15405929020
The take
The Take
The Vibe
Hunter's Head Tavern reads like a piece of the Virginia Piedmont landscape: its stone walls, low ceilings and thick, weathered masonry give the interior an inherited, lived-in quality. The copy presents the tavern as part of a long rural lineage—horse paddocks, century-old steeples and the Blue Ridge forming the backdrop—so the room feels both settled and regionally specific. Rather than a contrived concept, the tavern format is described as the building's natural condition, producing a classic, rustic and cozy atmosphere that leans into history and the rhythms of Hunt Country.
Best For
This is a country tavern best for relaxed daytime visits and approachable evenings. The listing explicitly highlights brunch and frames the kitchen around short supply chains and seasonality, making it a good pick for weekend mornings or leisurely lunches where local ingredients matter. The comfortable, historic interior and roadside location also suit casual hangouts with friends or low-key dinners after a drive through the countryside. It reads as a place where the setting and sourcing are the main attractions rather than a destination for late-night revelry.
Ordering Tips
The menu emphasizes proximity to named local farms and a kitchen that responds to what growers can deliver, so ask servers what’s freshest that day. Signature, hearty tavern dishes—fish and chips, shepherd’s pie and chicken pot pie—appear as anchors of the menu and are reliable choices when you want a sense of the kitchen’s comfort-food strengths. Because the menu ties tightly to season and local availability, be prepared for specials and daily variations driven by nearby producers.
Venue details
Ambiance
Cozy dining rooms in a restored 18th-century building with fireplaces, exposed beams, and hunt-country chic patios.
Tags
Vibe
Best For
Experience
Sourcing
Accessibility
At the Table
- Dress Code
- Casual
- Noise Level
- Conversational
- Service Style
- Upscale Casual
- Meal Pacing
- Standard
- Capacity
- Small
Signature Dishes
- fish_and_chips
- shepherds_pie
- chicken_pot_pie
Planning details
Location
9048 John S Mosby Hwy, Upperville, VA 20184 · Directions
Also consider
Also Consider
- Goodstone Inn, Notable alternative
- Harrimans Grill, American Cuisine, American Cuisine
- Side Saddle Cafe, Notable alternative
- Tremolo, Notable alternative
- Girasole, Notable alternative
Restaurant context
How Hunter's Head Tavern compares in Upperville
Hunter's Head Tavern is the practical, easygoing choice in this set. Choose it when value is measured by comfort, low planning pressure, a tavern atmosphere rather than by a highly choreographed dining experience. Goodstone Inn is the better cross-shop for a more formal countryside meal, while Harrimans Grill is the stronger fit if American Cuisine and a more polished setting are the point of the booking.
For a casual daytime stop, Side Saddle Cafe may be the cleaner match, especially if the meal is lighter or built around errands rather than an evening plan. Tremolo and Girasole are worth checking when the group wants a different mood, but Hunter's Head Tavern remains the simpler answer for diners who want a relaxed room and easier booking dynamics.
For special occasions, pick Goodstone Inn or Harrimans Grill if the room and service style matter more than convenience. Pick Hunter's Head Tavern when the celebration is intentionally casual, the group includes different ages or appetites, the plan benefits from a tavern setting that does not require overthinking.
Explore Upperville
Around this place
Discover more on Pearl
Unlock the full Hunter's Head Tavern guide in Pearl, including awards, comparisons, FAQs, planning details, and nearby places.
Compare Hunter's Head Tavern
| Venue | Location | Cuisine | Awards |
|---|---|---|---|
| Hunter's Head Tavern | Upperville | ; | No published awards |
| Goodstone Inn | Middleburg | ; | Star Wine Lists 20262026 Wine Spectator Best of Award of ExcellenceWorld's Best Wine Lists 2025Pearl Recommended Restaurants |
| Harrimans Grill | Middleburg | American Cuisine | 2026 Forbes 5-Star2026 Wine Spectator Best of Award of Excellence2026 La Liste Top Restaurants2025 Wine Spectator Best of Award of Excellence2025 Forbes 5-Star2025 La Liste Top RestaurantsWorld's Best Wine Lists 2023 |
| Side Saddle Cafe | Middleburg | ; | No published awards |
| Tremolo | Middleburg | ; | No published awards |
| Girasole | The Plains | ; | No published awards |
How Hunter's Head Tavern Upperville compares with similar nearby venues.
FAQ
Frequently Asked Questions
When is Hunter's Head Tavern open?
Hunter's Head Tavern is open 11 AM–8 PM on Monday, Thursday, Sunday, 11 AM–9 PM on Friday and Saturday. It is closed Tuesday and Wednesday.
What should I order at Hunter's Head Tavern?
Check the current menu before you go or when you arrive. No specific dishes or menu format are highlighted, so the safest approach is to choose based on the latest menu and the kind of casual meal you want that day.
Is Hunter's Head Tavern good for solo dining?
It can be a practical solo stop in Upperville if the hours work for your schedule. The hours are Monday, Thursday, Sunday from 11 AM to 8 PM, Friday and Saturday from 11 AM to 9 PM.
What should I wear to Hunter's Head Tavern?
Keep it casual. The dress code for Hunter's Head Tavern in Upperville is casual.
Is Hunter's Head Tavern good for a special occasion?
It is better framed as an easy casual choice than a formal occasion restaurant. For a more polished special-occasion meal, Goodstone Inn is worth comparing; Hunter's Head Tavern makes more sense when you want a relaxed Upperville option.
