Planning A Family-Friendly Middleburg Getaway for Labor Day Weekend


Labor Day has always been one of my favorite weekends, and a little family getaway can be the perfect way to close out the summer. One of my favorite Labor Day destinations is family-friendly Middleburg, Virginia.

Middleburg is a great getaway from DC because it’s only about an hour away.  It’s much more manageable than many of the other driveable trips out of the region. Plus, you’ll feel like you’ve totally escaped city life once you’re out in the country.

The biggest bonus? Kids love Middleburg!

Kid-Friendly Places to Stay in Middleburg

Red Fox Inn Middleburg, VAThe first step in planning your family-friendly Middleburg getaway is deciding where to stay.

Two favorite accommodations are The Red Fox Inn (prices ranging from $235-750 per night) and The Goodstone Inn (prices ranging from $375-548 per night), both brimming with country charm. The Red Fox is in the center of town, allowing you to walk to the shops and restaurants in Middleburg. The Goodstone is a bit further outside of town, so perfect if you’re looking for more of an oasis.

With a family, however, it’s generally much more convenient and affordable to stay in a VRBO or Airbnb property. Having your kids in their own rooms, or at least outside of your room, makes all the difference!

Many of the properties in the area are kid-friendly, and the owners are usually more than happy to help you plan your visit.

Family-Friendly Middleburg Dining Options

Middleburg Farmers MarketFor a small country town, you’ll be surprised to find how many wonderful restaurants and markets you can find in Middleburg!

Our favorite kid-friendly restaurant in town is the King Street Oyster Bar. The laid-back atmosphere and outdoor seating is perfect for children, and the food is delicious. I know it sounds crazy that some of the best seafood in the area can be found out in the Virginia countryside, but it’s true!

My husband loves the oysters, and I always go for the crab cake sandwich. Our daughter can be a very picky eater, but goes crazy over their cauliflower puree and blue crab dip. You really can’t go wrong here.

Another great spot is Hammerdown BBQ, just a short drive outside of Middleburg in Aldie. If you’re a meat eater, you won’t want to miss a chance to eat here. In fact, it was recently rated one of the best BBQ spots in the DC area by the Washington Post! If you’re taking Route 50 home from your trip to Middleburg, Hammerdown will be right there on the way home. It’s the perfect place to grab a bite on your way out of town.

If you’re looking for a lighter bite, check out Brassicas, just down the road from Hammerdown. It’s a must-visit for vegetarians and vegans. Almost everything on the menu is grown or harvested locally, so food options change with the seasons.

If you go the VRBO or Airbnb route for your stay, you’ll want to make sure you stop by the Middleburg Farmers Market. It’s held each Saturday morning through October 5 in the center of town. The locally grown fruits, vegetables, and flowers are out of this world!

Activities Kids Love to Do in the Country

Blue Ridge MountainsMany of the activities in Middleburg, Virginia are more adult-centric. Think wine tastings, upscale restaurants, and shopping in the boutiques. But, there are tons of fun things for kids to do, too.  

One of my family’s favorite things to do in the area is to go out for a hike at Sky Meadows State Park. You can make the hike as long as you’d like and will enjoy beautiful views of the Blue Ridge Mountains for most of the hike. If you’re feeling extra adventurous, you can even camp at Sky Meadows!

Another family-friendly Middleburg activity is watching an outdoor movie at The Salamander Resort & Spa.  Disney’s The Good Dinosaur (rated PG) will be shown on Saturday of Labor Day Weekend!

A unique Labor Day Weekend event in Middleburg is the Virginia Scottish Games at Great Meadow. It features traditional music including bagpipes, pipes, and drums; Scottish dog events, and children’s competitions. This event is both kid-friendly and dog-friendly!

No matter when you’re visiting Middleburg, it’s worth checking out whether there are any events being held at Great Meadow. There are often equestrian events your children will love.

Another fun place for kids in Middleburg is The Fun Shop, filled with amazing toys, clothing, and gifts for little ones. This is an especially great treat for kids if you’ve had them tag along with you to some of the other boutiques around town.

Of course, it’s always an option to just relax and enjoy the country. We love going on long walks on the country roads, and just enjoying the quiet you just can’t experience in the city. Even though it’s just an hour away, Middleburg feels like a world away. It is the perfect family getaway to close out the summer.