Middleburg is one of the most charming towns you can visit on a day trip from DC or a weekend trip! The town has gained a great reputation for its food, antiques, wine, and so much more. If you’re looking for the best of quaint, small town Virginia, then Middleburg is for you!
It took me far too long to take a day trip to Middleburg. Once I finally did, I was hooked. There are so many great things to do in Middleburg, VA, that you’ll love. So, without further ado, here are some suggestions!
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Shop for Unique Items and Antiques Downtown
While downtown may be small, there’s no shortage of great, local places to go shopping for unique finds here! The main street in town, where you’ll find shops, is Washington St., but you’ll also find them along some of the side streets, too.
Spending a morning grabbing a coffee from a local coffee shop like Common Grounds and strolling down Washington Street, stopping in shops, is a top-tier morning!
Antique shops in Middleburg tend to be highly curated with impeccable styling and curated touches, making it easier to imagine pieces within your own space, too. It’s one of those places home designers are known to frequent to source pieces and inspiration.
Grab a Bite (or Stay) at a Historic Inn
There’s no shortage of quaint, historic inns in Middleburg! Since it has been home to activities like horse racing and foxhound hunting, there’s been a long-standing need for places to stay.
Staying at one of these inns is an experience in itself, but even if you’re visiting just for the day, you can join in on the fun by making a reservation for lunch or dinner at one!
These inns are all unique and offer a different style of hospitality than you’ll find in cities just an hour away. It’s something you have to experience! Here are a few options to consider:
- The Red Fox Inn & Tavern (1728): Located right downtown, this is one of the oldest operating inns in the US. Reservations here sell out weeks in advance (even for lunch), so plan ahead! We learned this the hard way on our latest day trip.
- Goodstone Inn & Restaurant (1915): This spot is popping up for a second time on this list! This is a historic 265-acre estate with a Manor House, Carriage House, and French Farm Cottage. It features a beautiful farm-to-table restaurant and an outdoor pool.
- Welbourne Inn (1775): This historic bed and breakfast has been family-owned and operated for generations. It has a cozy feel and unique connections to Civil War history and writers of the Jazz Age in the 1920s and 30s.
Head to One of the Fun Town Events
Middleburg seems to be hosting a special event all the time! There is something on the city’s calendar happening every month. However, there are a few that the town is known for more than others. Below are a few to keep in mind!
- Christmas in Middleburg: The town turns into a Hallmark Christmas movie during the month of December! The charm is just turned up even more this time of year, but the event that Middleburg is best known for is its Christmas parade. Stay up to date on all holiday events here. December
- The Middleburg Hunt: Horse races and foxhound events are hosted in Middleburg. These events are heavily connected to the history of Middleburg. Spring and Fall
- Oktoberfest: While this is a newer event in Middleburg, it is a fun one! There’s not just beer during this event – there’s also local artisans, dog races, live music, and more.
- Art in the Burg: An annual art festival featuring work from local and regional artists in downtown Middleburg. May
Enjoy a Meal at a Local Restaurant
Many great restaurants in Middleburg are well worth dining at! If you couldn’t tell from this list, food and drink are a huge part of the fun in visiting. As part of that visit, you’ve got to stop at a local restaurant (or two if you’re staying longer than a day).
I would recommend that wherever you choose, you book in advance, especially on weekends. We made the mistake during our first visit of not making any reservations, and ended up walking around town for quite a while trying to find a spot with availability on a Saturday at 12:30 pm.
A few great restaurants are:
- Red Fox Inn & Tavern: historic and traditional American cuisine in a tavern setting, this spot is known as one of the oldest inns in the US
- King Street Oyster Bar: located right downtown, this spot has great seafood and cocktails in a casual setting. There’s indoor, outdoor, and bar seating. Great oysters!
- Conservatory at Goodstone Inn: for something upscale in a gorgeous setting, consider dinner for their tasting menu; lunch is much more casual.
- Harrimans at Salamandar Resort: special occasion spot offering seasonal flavors, local butcher’s cuts, fresh seafood, and imaginative desserts. Consider going for their Sunday brunch!
- Tremolo Bar: modern wine bar with small plates, they also offer a large tasting menu that looks divine!
Take a Hike on a Nearby Trail
Middleburg is located in the foothills of the Shenandoah Mountains so you’ll find some great hikes just 20 minutes or less from town. If you want to venture even further (30-45 minutes), you’ll find Shenandoah National Park and beyond.
Below are a few great hikes just 20 minutes or less from Middleburg.
- Sky Meadows State Park: This park offers great views of the rolling hills and farms that cover the region. With over 20 miles of trails, there’s little tree cover, depending on the trail you choose, so I’d recommend avoiding the hottest part of the day when visiting. I’d recommend:
- Lost Mountain Trail: rewards with great views on a 4-mile loop
- Piedmont Overlook: fastest route to the view, but it is a steep climb (2.2 miles)
- Leopold’s Preserve: This 380-acre nature preserve offers seven miles of easy-going nature trails through rivers and trees.
- Banshee Reeks Nature Preserve: More than 20 miles of hiking trails criss-cross the 695-acre Banshee Reeks Nature Preserve, which includes forests, fields, ponds, and streams.
Discover Civil War History
Middleburg played an important role during the Civil War as a hub for cavalry engagements during the Gettysburg Campaign. Today, you can visit the Mount Defiance Historic Park to learn about the lead-up to the turning point of the Civil War in Gettysburg.
The park features historic buildings, including a mill and a blacksmith’s cottage. There are several historic markers and plenty of things to learn while here.
Bonus: Close by is the Mount Defiance Cidery and Distillery, where you can grab a drink after your visit! They also host fun events like sip and paints, so check their calendar!
Sip and Savor at local Wineries
One of the main draws of this area are the fantastic wineries with views of the rolling hills in this area. There’s no shortage of wineries between Washington, DC and Middleburg, no matter which route you take to get there.
In Middleburg and the entire Northern Virginia region, you’ll typically find wines made from grapes like Norton (dry red), Viognier (dry white), and Cabernet Franc (medium red), and Bordeaux-style blends like Cabernet Sauvignon, Malbec, Merlot, and Syrah.
A trip to Middleburg is incomplete without a winery visit. Many offer non-alcoholic wines, live music, and food. There’s truly something for everyone! A few great options are below:
- Boxwood Estate Winery: smaller tasting room with a full food menu, it’s recommended to make reservations in advance as they fill up quickly – especially on weekends
- Cana Vineyards & Winery: just outside town, fantastic views, sparkling non-alcoholic wine options, and live music regularly
- Chyrsalis Vineyards: one of the few vineyards in the area open past 6 pm, great pizza and salads, beautiful grounds, and outdoor seating
- Greenhill Winery & Vineyards: adults-only vineyard with a large outdoor space, fabulous mezze menu
Did you know that the first wine in the US was made in Virginia? The practice of winemaking in Virginia dates back to 1609, when the earliest Jamestown settlers planted vines and attempted to grow grapes. They were somewhat successful, but it took a few centuries before wine was really successful in the state!
Learn about Sporting History at a Museum
Middleburg, Virginia, known as the nation’s “Horse and Hunt Capital,” has interesting museums that offer a glimpse into the region’s history. Middleburg has a history of raising Fox Hounds and of sporting activities such as horse racing, fishing, and polo.
I don’t know about you, but I didn’t grow up with much knowledge about these things, so the museums in Middleburg were a perfect fit for learning something new and different. Both museums are fairly small and do have limited hours, so plan ahead and check that they are open!
Both museums are right downtown and easy to visit in an hour or two.
- National Sporting Library & Museum – open Wednesdays to Sundays
- Masters of Foxhounds Museum – open Mondays, Wednesdays & Fridays
Relax with a Spa or Pool Day
One thing about Middleburg is that there are some beautiful boutique and luxury inns as well as spas. You can spend an entire day just relaxing by a pool or get a treatment or two for a perfect day in the countryside.
The resort that is most famously known is the Salamander Resort. It’s the only five-star resort in the state of Virginia. If you want an amazing spa treatment, this is the perfect place. The resort itself is also beautiful and well worth a visit if you want to make a reservation for lunch or dinner at their restaurant.
Another great pool day you can find on ResortPass is the Goodstone Inn. This historic property is beautiful and offers great views of the rolling hills. You can also make reservations at one of their two restaurants here.
I hope this list of things to do in Middleburg, VA brings you inspiration for your trip! It’s a great getaway from DC, whether you go for a day or stay for a weekend. I love going here for the day to explore. For such a small town, I am always surprised to find something new and unique here!
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