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The Commonwealth of Virginia is home to picturesque pockets of countryside and small-town charm. From posh wineries and boutique hotels to bucket-list adventures and historic sites, there’s something for everyone within these three small towns. Middleburg, Lexington, and Abingdon are all enchanting in their own ways. Come explore!

Middleburg, VA
The “Horse and Hunt” Capital of the Country

A jaunt in Middleburg will plop you into a Jane Austen scene in the English countryside. Picturesque landscapes, low stone walls, and stately horse farms envelop this town that’s just an hour from D.C. in wine-famous Loudon County. The settlement was established in 1728 as a fieldstone tavern on an old Native American trail by a cousin of George Washington. That tavern became the Red Fox Inn, which is the heart of Middleburg still today. At the turn of the 19th to 20th century, the town became a popular destination for foxhunting and steeplechasing, earning it a reputation as the “Nation’s Horse and Hunt Capital.”

Red Fox inn Middleburg

With more than 160 buildings listed on the National Register of Historic Places (including the Red Fox Inn), Middleburg is known for its natural beauty, historic charm, and Southern hospitality. Image: Visit Middleburg

The historic downtown is lined with chic boutiques, dapper men’s stores filled with tartan plaid and leather-clad riding gear, and cuisine that spans from fireside tavern fare to farm-to-table gourmet. Posh lodgings are sprinkled all over Middleburg. You can’t go wrong with a room at the historic Red Fox Inn, the five-star Salamander Resort, or the elegant Goodstone Inn & Restaurant, which has been named one of the best restaurants and best wine restaurants in America. Salamandar’s Harrimans Virginia Piedmont Grill garners rave reviews for its flavorful, locally inspired dishes, while Hunters Head Tavern and Red Fox Inn’s restaurant serve fresh takes on traditional tavern fare. Try Common Grounds for delicious espresso and bagel sandwiches.

Middleburg CHristmas Parade

Christmas in Middleburg is a tradition that celebrates lots of the area’s sporting animals, like beagles and horses. Image: Visit Middleburg

The National Sporting Library & Museum has a trove of fine art, books, and exhibits about Middleburg’s heritage and tradition of country pursuits like angling, steeplechasing, foxhunting, flat racing, polo, and more. Nearby mountains create a scenic backdrop and an ideal grape-growing climate. There are 20 wineries within half an hour’s drive, like local favorites Greenhill Vineyards and Boxwood Estate Winery.

Whether you’re looking for a luxe spa retreat, a fun vineyard day, or a taste of equestrian life, Middleburg’s got it!

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Salamandar Resort

You could fill an entire long weekend exploring Salamander Resort‘s 340 acres of amenities and adventures. They have a well-appointed spa, cooking studio, riding stables, zip-lining, archery, nature trails, tennis, heated pools, and more. Image: Facebook

Lexington, VA
Civil War History Meets College-Town Cool

This gem of a small town is tucked away in the Shenandoah Valley, but close enough to I-81 to make it accessible from many big cities. It’s got a rich history, two colleges (Washington & Lee and Virginia Military Institute), and outdoor scenery strewn across its Rockbridge County home. The two institutions have created an ever-growing demand for boutique hotels, wine bars, and trendy shops. With only a few stoplights, you can explore downtown and both campuses easily on foot. Once you’ve hit the in-town sites like W&L’s University Chapel & Galleries and the VMI Museum, there is more to see nearby.

Lexington VA

Lexington was established in 1777 as the county seat and named for the Battles of Lexington and Concord that marked the beginning of the American Revolution (Source). Image: Chris Weisler | Rockbridge County Tourism

Pumkinseeds Lexington BA

Pumpkinseeds is a beloved and well-stocked shop … one of many that are photo-ready along Main Street. Image: Chris Weisler | Rockbridge County Tourism

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Stay at The Georges, a thoughtfully restored, 200-year-old inn ranked #4 Best City Hotel in America in the 2021 Travel + Leisure World’s Best Awards. In the morning, locals grab their own mug off the wall at Lexington Coffee Shop and head for the serve-yourself station of delicious, locally-roasted brew.

Just down the road, Pure Eats is making fresh donuts and bagels for an easy breakfast. This is no better Lexington lunch than Blue Sky and waiting in the inevitable queue is worth it. People flock to this family-run corner eatery for their homemade focaccia, soups, and sandwiches. Bistro On Main and Southern Inn are cozy old-school staples for supper, or enjoy creative fare at The Red Hen or Haywood’s. Grab a fireside nightcap in the TAPS living room or a local brew at the super-cool Heliotrope Brewing.

Haywood's The Georges

With a reservation at Haywood’s Piano Bar and Grill, you’ll find more than just chef-driven cuisine and creative cocktails. Nightly live entertainment by the town’s top players makes this the musical crossroads of the town. Image: The Georges

Outdoor wanderers shouldn’t miss the Chessie Nature Trail, a flat, six-mile trail along an old rail bed and the Maury River, running from Lexington all the way to Buena Vista. For a more challenging trek with hugely worth-it views, head up House Mountain, or tube down Goshen Pass. Just miles down the road is Natural Bridge State Park, one of the nation’s top natural wonders. Whether or not you’re traveling with kids, Boxerwood Nature Center & Woodland Gardens is a whimsical, off-the-beaten-path gem that’s worth exploring.

Abingdon, VA
Outdoor Adventure Meets On-Stage Culture

Close to the Tennessee border is the eclectic little town of Abingdon. Known as a respite for many Appalachian Trail hikers, it’s filled with funky and hospitable people and businesses. Book a room at a quaint bed and breakfast — like Black Fort’s Inn — or opt for the stately four-star Martha Washington Inn & Spa (lovingly called The Martha) for a well-situated home base. It’s across the street from the famous Barter Theatre, the longest-running professional Equity theatre in the United States. No matter what’s playing, you can plan on an unexpectedly entertaining night.

One of the most extraordinary things about this town is its connection to the Virginia Creeper Trail. Pick one of these bike shops in town to rent your bikes and get shuttled to the top of the 35-mile-long trail. It’s almost all downhill from there. This famous bike trail meaders down an old rail bed that hugs rivers and streams and crosses the Appalachian Trail a few times. Dotted with a few chances to refuel with snacks and ice cream, you’ll work up a great appetite for the rest of your Abingdon weekend.

Main Street Abingdon VA

Though Abingdon is great to visit year-round, it boasts some seriously brilliant fall foliage along Main Street. Image: Jason Barnette

Virginia Creeper Trailer

Sweeping views and little towns are perfect stops for a picnic, ice cream, or a beer. The Creeper traverses the famous Appalachian Trail a few times, so you can greet brave backpackers on the way to their next stop. Image: Facebook

The Tavern

Ask the host or the waiter at The Tavern about the ‘special letters’ table. Image: Jason Barnette

If The Tavern is Abingdon’s oldest and most famous restaurant, Foresta is its modern, eclectic new counterpart serving up elevated Italian and Mediterranean dishes, and 128 Pecan is a no-frills farm-to-table option. Grab a cocktail at Rain, a beer (and a concert) at the Wolf Hills Brewing, and coffee at Wolf Hills Coffee as you walk through the Abingdon Farmer’s Market.

One thing you can expect around every corner in Abingdon, Lexington, and Middleburg, is friendly locals ready to help you find out why they love their towns. Go see why small-town Virginia truly is for lovers!


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