Travel Guide: Middleburg, Virginia

Nestled in the heart of Virginia's picturesque countryside lies the charming town of Middleburg. Known for its equestrian heritage, historic charm, and scenic landscapes, Middleburg offers a peaceful escape from the city seeking a taste of rural elegance and equestrian culture. Located just an hour outside of DC, it is the perfect day adventure with great shopping, restaurants, and things to do for everyone. This guide are just a few of my favorite things to do in Middleburg and the surrounding hunt country.

Discovering Middleburg's Equestrian Legacy

For me, Middleburg isn't just a destination; it holds precious memories from my childhood. I spent many weekends here, competing in horse shows and soaking up the town's deep equestrian culture.


One of my favorite ways to start the day out in Hunt Country is with a hike at Sky Meadows State Park. The park is rich in history with 22 miles of hiking trails that have amazing views of hunt country. Sky Meadows is located less than 20 minutes from downtown Middleburg. Once you come back to town, my favorite things to do include visiting the National Sporting Library and Museum, stopping at Greenhill Vineyard, shopping at the unique boutiques, going antiquing, and enjoying a good bite to eat at the plethora of restaurants.


Breakfast and Lunch

Salamander Market: gourmet market that offers an indulgent country breakfast and lunch menu. The biscuit breakfast sandwiches are one of the best breakfast sandwiches I have ever had! Common Grounds my favorite spot for a quick cup of coffee and a pastry. The Upper Crust is a bakery with soup and sandwiches and a small town feel. With minimal advertising, their customer base is largely word of mouth and if you visit once you will find yourself going back for their addictive French Crullers. For a more upscale sit down lunch, I would recommend Tremolo Wine Bar. The menu is elevated and they have a unique wine selection. They also have a lovely, dog-friendly patio to enjoy when the weather is nice. Two other favorites of mine are located outside of the town. Hunter's Head Tavern is in Upperville, Virginia, which is the town next to Middleburg. Hunter's Head is worth the ten minute drive and is the most charming, authentic English pub with a lunch and dinner menu. There is also a dog-friendly patio that is covered and heated in the winter for year-round use. Lastly, on your drive back in from a hike at Sky Meadow, do not miss the Locke Store in Millwood, Virginia. The country store and deli has sandwiches that are so good you might go back up to order a second. The roasted turkey club on ciabatta bread and the chocolate chip cookie is the perfect combination.


Red Fox Inn and Tavern is my go-to! The tavern is so cozy and the food is amazing. Hunter's Head Tavern, Tremolo Wine Bar and King Street Oyster Bar also have good food and a good dinner menu! The Goodstone Inn, Lost Barrel Brewery and Bluewater Cocina are on my dinner bucket list. I have not eaten at these spots yet, but they are on the top of my list to try.


My favorite boutique to frequent is Tully Rector. They have been in business forever and are in a larger space now. From basics to cocktail dresses, they have it all! Note: it is closed on Sundays. Courtney Kennedy is another boutique that always has unique, emerging designers. It is located off the beaten path and worth the walk down Marshall Street. Creme de la Creme is the cutest gift shop with all kinds of home goods and decor. I always stop here during my trips to Middleburg! Atelier Design & Decor is one of my favorite design stores! The shop is filled with vibrant home goods and furniture. Every time I visit, I want to buy out the store! Antiques on Washington Street there is something for everyone and obsessed with all of the sporting antiques that fill this space. Brick and Mortar Merchantile has the best country gifts and upscale home decor. The merchandise is typically American-made or from local artisans. They are also hosting my pop-up on May 18 and 19! Nature Composed is the last stop on my list! It is the cutest flower shop to pick up a plant or bouquet to add to your garden or home.


I do not stay overnight often but I would check out the Red Fox Inn or the Goodstone Inn! They are both charming inns and often more reasonably priced than other hotels in town!

Middleburg has so much to offer! I know I missed some amazing spots, but these are a few of my favorites! What should I add to this list? Also, be sure to check out the calendar of events because there are often horse races, art events, and farmers markets in town!