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    The Middleburg, VA Travel Guide

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    For a cozy weekend getaway filled with fresh air, scenic hikes, warm fires, delectable bakeries, and smooth wine, we pick Middleburg, the heart of Virginia’s beautiful hunt country. From your active days to stargazing evenings, you’ll fall in love with this charming destination.

    The Middleburg Bucket List

    Where to Stay

    • ​​Red Fox Inn

      This is an iconic Middleburg spot, and the oldest Inn in America. If you don’t stay there, you must try their restaurant!

    • ​​Goodstone Inn

      This is only about ten minutes out of town, is a very romantic option, and offers lots of activities.

    • Salamander Inn

      This is a great option if you are looking to try a newer property, complete with a spa, restaurant and an easy walk to town.

    • ​​Ashby Inn

      Located in Paris, VA, this is a super-cute spot with well-decorated rooms. It has an amazing restaurant for brunch or dinner, and is close to the Sky Meadow State Park, a great hiking spot! Tuckernuck Tip: The Inn will pack you picnics if you order ahead, which you can take with you to the park!

    Breweries and Vineyards to Visit

    • RdV Vineyards

      This is the best wine in Virginia! You have to call and make a reservation. Tuckernuck Tip: The private tour is worth it.

    • Old Ox Brewery

      There are limited outdoor seating options, but this is still a very convenient option in town.

    • Lost Barrel Brewing

      This is a new spot to try, right outside of town, and very fun for groups. Tuckernuck Tip: Reserve an outdoor firepit!

    • Dirt Farm Brewing

      About twenty minutes outside of Middleburg in Bluemont, VA, this spot has beautiful views and great beer! Tuckernuck Tip: Stop here post-hiking!

    • Greenhill Vineyards

      Grab your friends to experience a serene setting and high-quality wine here.

    • Slater Run Vineyards

      Be sure to check out the newer tasting room!

    • Three Fox Vineyard

      A more casual spot with great wood-fired pizza, this is one of our favorite places to visit after hiking at Sky Meadows.

    • Boxwood Winery

      This is definitely a late afternoon spot since it closes at 6 pm, but go for the $10 tastings!

    Activities to Do

    • Hike at Sky Meadows

      Even if you just stroll along the pasture side, the views are beautiful.

    • Visit the National Sporting Museum

      Learn about equestrian, angling and field sports by exploring the museum’s exhibitions with literature, art, and more.

    Where to Eat


    • Common Grounds

      Fuel up here before a hike with coffee and breakfast sandwiches!

    • Hunter's Head Tavern

      A fifteen-minute drive from Middleburg, this brunch spot is located in Upperville, VA.


    • Market Salamander

      On a busy, activity-filled day, this spot is ideal for a casual lunch.

    • The Locke Store in Millwood

      This is a modern country store and deli that offers delicious to-go meals to grab after hiking at Sky Meadows. Plus, they have complimentary wine, beer and cider tastings on the weekends!

    • Upper Crust Bakery

      The best bakery ever! Like, in the world, in our opinion.


    • Harrimans Restaurant in Salamander Inn

      Located in a luxury hotel, this is a fun and yummy spot for light bites.

    • Red Fox Inn Restaurant

      A historic landmark, this restaurant has an intimate setting and offers delicious tavern dining.

    • King Street Oyster Bar

      This is a fun, more casual dining option for brunch, lunch, or dinner.

    • The Front Porch

      A favorite spot if you venture to The Plains, The Front Porch has great sandwiches, a delicious menu, and a cozy atmosphere.

    • The Buttery

      Part of The Locke Store in Millwood, this is ideal for a delicious dinner in a classic cabin setting after a day of hiking.

    • Field & Main

      If you venture to Marshall, VA we recommend this restaurant for locally-sourced fare.

    Where to Shop

    • Creme de la Creme

      Here you will find beautiful, charming housewarming gifts, or treasures for your own home.

    • Red School House Antiques

      Others We Love: Fox & Pheasant in Boyce, VA, Another Blue Moon, Antique Emporium, Vilnis Antiques in Strasburg, VA.

    • Little Lambkins

      A favorite spot for quality and classic clothing for your or your friends' little ones!

    For more ideas, check out Visit Middleburg before you go to see if there are upcoming events. You’ll find news of horse races, art shows, and more!

    Happy travels!

    All my best,