The Middleburg, VA Travel Guide | Tuckernuck

The Middleburg, VA Travel Guide

By Tuckernuck on

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 Firm 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,