ISO rider-friendly lunch suggestions in Middleburg/The Plains/etc

My wedding anniversary and weekly lesson happen to fall on the same day. Mr. Carrots, being a resigned and patient sort, has suggested that he tag along to the barn and we go out to a leisurely lunch afterward. (Bless the man, he didn’t even think to suggest that I cancel with my trainer. He’s learned a lot.)

Would love recommendations on places reasonably close to Middleburg that are nice/festive, but not so nice that I’ll frighten the other patrons (maybe there’s a patio involved…?). I can tidy up with a wash rack hose, baby wipes, and a fresh shirt, but a full shower and change isn’t an option because I’ll have to come back and do evening barn chores. (So as one of the Baby Carrots says, what’s the point of getting clean if I’m just going to get dirty again?)

If you’ve ever dined somewhere reasonably close to Middleburg in breeches and pinned-up hair (and not been stuck in Siberia next to the kitchen), I’d love suggestions! My first thought was the Red Fox, but they only do dinner.

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I lived in Middleburg for a few months. I believe Market Salamander is open for lunch, I’m thinking Girasole or Railstop, in the Plains but I think those are only open dinner too. Both great. If you want an inbetween of come after riding, but nice I’d go to Hunters Head Tavern in Upperville. I believe they did a brunch at one time.

On my days off, I would always run by Upper Crust right beside Safeway. It is not fancy at all, but I can taste the Rooster Sandwich now and they have baked goods. I think they only accept cash. But, it’s convenient to park, eat lunch, then walk to all the shops.

I have been to King Street Oyster Bar a few times. When I go up by myself, I usually order the Gumbo, takeout.

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I would go to Hunters Head, but I love the food there.


OMG the King Street Oyster Bar. MY FAVE.

Dank’s Deli (2nd choice)

Upper Crust


Red Horse Tavern.

None were bad choices. And yes Hunter’s Head in Upperville is also fantastic.


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King Street Oyster Bar would be perfect! Any attire is fine, and the food is great. You could wear riding pants or dressy clothes and fit in equally well.

Market Salamander, Upper Crust, and Dank’s Deli as others have mentioned are also great, but more of “order at the counter” type of places. If you want a sit down place, King Street or Red Horse Tavern would appropriate.

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I lived In Delaplane for a few years and practically resided at Hunters Head. I mean we ate there at least once a week, it is that good. If I recall correctly the majority of their menu is farm to table. If you really want to have an out of body experience, add their goat cheese and avocado to your burger. Never had anything but a great experience there.

But really anything in the Middleburg area is good. I don’t think I’ve ever had a bad meal in that area. Red Horse, Rail Stop, etc were regular stops for me. I really miss breakfasts at the Coach Stop, which no longer exists.

Wherever you go, you’ll be in good company with fellow horse folk. There’s always someone in riding clothes. And the ones who aren’t are DC day trippers who wear faux/fashion “equestrian” attire. :rofl:

Whatever you decide, don’t forget to follow up your lunch with ice cream from Scruffy’s!! :smiling_face_with_three_hearts:

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Honestly anywhere. I have never felt out of place in riding clothes in Middleburg or the surrounding areas. I usually err on the side of “lesson attire” (tucked in quarter zip with breeches and belt, etc) if I know I’m going somewhere nicer after, but odds are you won’t be the only person coming straight from the barn wherever you go so I wouldn’t think twice about it.

I’ll echo King Street Oyster Bar as a favorite, riding clothes or no. They have a patio if you really feel too dirty to sit inside, and their happy hour is also excellent depending on when you’re planning to go. I usually duck into Old Ox brewery if I have to kill time waiting for a table. And would recommend following up dinner with ice cream at Scruffy’s for a delicious dessert that benefits local rescue animals!

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THIS ^^ I felt more out of place without my riding gear on when I was out and about in town. Its been so long since I have been in Middleburg. My go to places were Mosby’s, Magpie and Huckleberries!

I would go to Hunters Head. Its owned by Sandy Lerner / Ayrshire Farm.

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Thank you all for the great suggestions! I appreciate it.

another vote for Hunters Head.