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Things to do in Middleburg

Top recommendations from locals

From sightseeing to hidden gems, find out what makes the city unique with the help of the locals who know it best.
Lodging
$$$
“Great find dining restaurant in an historic building. Try the fried chicken!”
  • 14 locals recommend
Resort
“This is where you go if you want to book a spa treatment during your stay in Middleburg. You might want to do this prior to your arrival as their times book up fast.”
  • 13 locals recommend
Library
“The National Sporting Library is wonderful for those who appreciate art and anything equestrian! Check out their current exhibition! About eight miles away!”
  • 12 locals recommend
Café
“Local coffee shop with great sandwiches for breakfast and lunch. My favorite is the Federal on a Gluten Free wrap!”
  • 9 locals recommend
Restaurant
“If you love seafood, King Street food is always delicious, very reliable. Fun happy place. Easy environment, full range of menu items and cocktails. ”
  • 8 locals recommend
Lodging
“They have an amazing fine food restaurant, as well as a great casual french bistro.”
  • 5 locals recommend
Grocery or Supermarket
$$
“If you need to grab a few groceries or essentials before your stay at The Whistle Stop, Safeway is always a safe bet.”
  • 3 locals recommend
Winery
“Greenhill offers rolling hill views and spectacular wine. Adults only on this visit- no one under 21 allowed. The bruschetta is worth a trip by itself. ”
  • 6 locals recommend
Bakery
$
“The Upper Crust is a quaint bakery and café specializing in cookies and pies, with sandwiches and some breakfast options. Home of the famous Cow Puddle Cookie!”
  • 6 locals recommend
Restaurant
“Your typical sports bar with nice outdoor seating and big TVs inside. One of the few spots open late in town. ”
  • 4 locals recommend
Bakery
$$$
“Market Salamander offers a wonderful, quick breakfast and lunch. Their chicken fingers are a crowd favorite for young and old. Don't forget to ask for the honey mustard to go with them!”
  • 3 locals recommend
Winery
“Stunning modern tasting room and facilities make this a must stop while you are visiting! Thought by most to be the "best wine in the region".....go take a look and have a sample.”
  • 5 locals recommend
Store
“Purely local "everything" shop - boasting beautiful equestrian home decor and kitchen gadgetry. Cards, candles and toys round out this seasonally specific shop. Never leave empty handed...there's something you'll surely need!”
  • 3 locals recommend
Food
“Chrysalis Winery has a friendly atmosphere and gives you a good flavor for the Middleburg area.”
  • 2 locals recommend
Restaurant
“The best coffee and breakfast in town. Great lunches and dinner too. If you like to cook, check out their locally raised, organic meat selection from their family farm.”
  • 3 locals recommend
Thai Restaurant
$$
  • 2 locals recommend

Top restaurants

Lodging
“Great find dining restaurant in an historic building. Try the fried chicken!”
  • 14 locals recommend
Café
“Local coffee shop with great sandwiches for breakfast and lunch. My favorite is the Federal on a Gluten Free wrap!”
  • 9 locals recommend
Restaurant
“If you love seafood, King Street food is always delicious, very reliable. Fun happy place. Easy environment, full range of menu items and cocktails. ”
  • 8 locals recommend
Restaurant
“Your typical sports bar with nice outdoor seating and big TVs inside. One of the few spots open late in town. ”
  • 4 locals recommend
Bakery
“Market Salamander offers a wonderful, quick breakfast and lunch. Their chicken fingers are a crowd favorite for young and old. Don't forget to ask for the honey mustard to go with them!”
  • 3 locals recommend
Restaurant
“The best coffee and breakfast in town. Great lunches and dinner too. If you like to cook, check out their locally raised, organic meat selection from their family farm.”
  • 3 locals recommend
Sushi Restaurant
“Surprisingly great sushi restaurant for being way out here in the country. Great for take out as well.”
  • 5 locals recommend
Thai Restaurant
  • 2 locals recommend

Get to know Middleburg

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