11 Serene Virginia Towns For A Weekend Retreat
Nicknamed the Old Dominion, Virginia is home to a broad range of charming towns that offer a wonderful weekend escape from the hustle and bustle of city life. With populations below 50,000, each town enjoys scenic landscapes, a rich history, and unique attractions that make them ripe for exploration. Whether you're interested in historical landmarks, picturesque views, or comfortable accommodations, you’ll be calling any of these destinations “home sweet home” before you know it. Known as the birthplace of eight U.S. presidents and home to more Civil War battlefields than any other state, Virginia’s story runs deep—and you’ll feel it in every corner, from presidential estates in Charlottesville to the vintage charm of Staunton’s brick-lined streets. Below are 11 serene towns you should consider for your next Virginia adventure.
Staunton
Similar to Charlottesville, visitors are sure to get their fix of U.S. history in Staunton, which was settled in 1732 and served as the capital of the Northwest Territory from 1738 to 1771. Woodrow Wilson was born in the Greek Revival Manse that now houses the Presidential Library and Museum, where you’ll learn all about the life of the 28th president. Staunton fuses a small-town vibe with a vibrant cultural scene. Marvel at beautiful Victorian architecture, stroll red brick sidewalks, browse quaint downtown boutiques, and grab a bite or drink at popular establishments like Brick Restaurant and Pub.
Whether you enjoy hiking, cycling, or taking in breathtaking views, you’ll connect with nature at any of Staunton’s parks, including the sprawling 214-acre Gypsy Hill Park. Though options for accommodations abound, The Blackburn Inn, constructed between 1825 and 1828 and boasting cozy rooms, has an interesting history behind it: The inn began as the Main Administration Building for the Old Western State Hospital, committed to the emotional well-being and humane treatment of patients.
Charlottesville
Charlottesville, established in 1762 and named for Charlotte Sophia, consort of King George III of England, combines a rich history and scenic rivers and waterways with lively shops and restaurants. No weekend trip to this town of around 46,000 residents would be complete without a visit to Monticello, the home of Thomas Jefferson, and the University of Virginia, which the third U.S. president himself founded. Boasting marvelous architecture, both comprise a single UNESCO World Heritage site, with the former being the only presidential and private home to make the esteemed list. Just a half mile below Monticello is Michie Tavern, where you can enjoy a bite or drink in a charming 18th-century setting.
Voted a 2024 Top Adventure Town by Blue Ridge Outdoors Magazine, the town’s splendid location near Shenandoah National Park means ample opportunities for biking, hiking, and fishing. Ready to call it a day? The luxurious Inn at Court Square, built in 1785, is the oldest existing house in downtown Charlottesville.
Lexington
If the Civil War is more your thing, Lexington, a small town of over 7,000 people tucked into the Shenandoah Valley, makes an ideal destination for an enriching weekend getaway. The home of the Confederate General Stonewall Jackson is located here, as is the final resting place of Commanding General Robert E. Lee. To learn more, visit the 1749 Washington & Lee University, where Lee served as president following the Civil War. Also steeped in history is The Georges, a five-building property where you can rest your head after a busy day of sightseeing. Its Georgian-style Washington building dates back to 1789, the same year George Washington was sworn in as president.
Great water views, hikes, and picnics can be had at the Chessie Trail, which parallels the Maury River from East Lexington to Buena Vista for seven miles. Take pictures of eye-catching flora and fauna at the 15-acre Boxerwood Nature Center and Woodland Gardens if time allows.
Abingdon
Eighteenth-century buildings, immersive cultural activities, and a wealth of recreational opportunities come together nicely in Abingdon. The town was established by an act of the Assembly of Virginia in 1778. Two years later, Patriots from North Carolina and Virginia convened at the Muster Grounds to initiate a 300-mile march to Kings Mountain, South Carolina. The resulting battle was a turning point in the Revolutionary War, helping the young nation secure its independence.
Amble along the brick sidewalks of Abingdon’s 20-block downtown, and you’ll discover striking architecture bridging two centuries of history, from The Tavern, Virginia’s oldest bar, to inviting small-town American storefronts. Plus, the Martha Washington Inn & Spa, built in 1832, features 63 elegantly appointed guestrooms, a spa, and a fitness center. Named one of the Best Small Towns in the South by Southern Living Magazine, Abingdon is just too good to miss!
Middleburg
Affectionately dubbed The Nation’s Horse and Hunt Capital, this lovely town set against the backdrop of the Blue Ridge Mountains boasts fine fare, historic attractions, and unique antiques. Middleburg was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman Leven Powell, who bought the property from Joseph Chinn, a cousin of George Washington. Powell changed the name from “Chinn’s Crossroads” to Middleburg, as the town marked the halfway point between Winchester and Alexandria along the Ashby Gap trading route, known today as U.S. Route 50.
From art galleries to high-end boutiques, shoppers will no doubt have great finds to take home with them. Foodies can delight their taste buds at popular stops like Middleburg Common Grounds and Hunter’s Head Tavern. The region is home to Greenhill Vineyards, one of the oldest vineyards in Northern Virginia, and several local breweries. Ready to kick back and relax? The Red Fox Inn & Tavern, a Middleburg jewel since 1728, encompasses five painstakingly restored historic buildings and houses with twenty-two comfort-inducing inn rooms, suites, and cottages.
Culpeper
Though Culpeper is merely an hour from Washington, D.C., the tranquil pace here makes it feel worlds away. Culpeper was established in 1759 and was known as Fairfax and Culpeper Court House before a new charter gave it the name of Culpeper in 1870. Lining the area’s Historic Downtown are cafes, farm-to-table eateries, and antique shops. Head over to The Museum of Culpeper History to learn about the town’s rich past, from the Triassic period 215 million years ago to the present day. The local culture is also on display during community events like the Fourth of July festivities and the Libations street fair. Within walking distance of downtown is Fountain Hall, which features six charming guestrooms and suites, all with private baths. If the outdoors is calling, make your way to the Shenandoah National Park for camping, hiking, paddling, or bird watching. Spanning nearly 200,000 acres, it is an abode of endless flora and fauna.
Orange
Just 30 minutes south of Culpeper lies Orange, so named in honor of William IV, Prince of Orange. History abounds in this small town, and enthusiasts have many options to explore. Montpelier, the estate of James Madison, the fourth President of the United States, aims to preserve the legacies of the Madisons, the U.S. Constitution, and the enslaved community. You’ll learn more about the fourth president at the James Madison Museum, which features period items like furnishings, jewelry, clothing, correspondence, and books. Speaking of books, the Orange County Historical Society’s library contains more than 2,000 volumes.
If all that history makes you work up an appetite, stroll over to Orange’s Historic Downtown, where charming eateries and shops abound. Barboursville Vineyards, which boasts a 900-acre vineyard and tasting room, is open seven days a week. For lodging, luxury bed and breakfast Mayhurst Estate is a haven of warmth and hospitality built in 1859 by President Madison’s great nephew, Col. John Willis.
Warrenton
The county seat and largest town in Fauquier County, Warrenton, is the gateway to Virginia’s Piedmont Region. It was at the junction of the Alexandria-Culpeper and Falmouth-Winchester roads, where a trading post known as the Red Store was established, that this charming town’s story begins. A settlement had begun taking shape around the time of the American Revolution, and by 1790, the first courthouse was built. Richard Henry Lee donated over 70 acres of land for the county seat, which was incorporated as the Town of Warrenton in 1810.
Whether you’re big on horses, wineries, or beautiful views, all three are plentiful in this endearing town of over 10,000 residents. Historic Old Town Warrenton is tucked into the heart of town, offering everything from shops and restaurants to the Old Jail Museum, now the proud home of the Fauquier Historical Society. While there, explore artifacts pertinent to the Revolutionary era and Civil War, among other Fauquier County historical exhibits. From Vint Hill Craft Winery to Mediterranean Cellars, you have myriad options for tastings and wine-themed events. After some drinks, retreat to Airlie Hotel, which is set on over 300 fantastic acres of rolling farmland, and a countryside retreat designated a Historic Hotel of America.
Bedford
The Town of Bedford was established in 1782 as the village of Liberty, with the name changed to Bedford City in 1890. Currently, the town covers approximately nine square miles, and around 7,000 residents call it home. If you want to learn more about Thomas Jefferson without the crowds characteristic of Monticello, visit the lesser-known Poplar Forest. This National Historic Landmark was his personal retreat and plantation — a place where he could read (he kept 1,000 volumes here), study, and contemplate a couple of times a year outside of the public spotlight.
The National D-Day Memorial remembers and honors those who participated in the largest amphibious invasion in military history during World War II. In addition, three hundred years of history are documented at the Bedford Museum and Genealogical Library, where you’ll spot interesting exhibits across three floors. For a different experience, unwind and snap plenty of photos at nearby Smith Mountain Lake, which boasts 500 miles of scenic coastline and 20,000 acres of unspoiled waters, along with enough shops, restaurants, and recreational activities to keep the whole family occupied. Stay at The Inn & Forest Oaks, a splendid bed and breakfast featuring six guestrooms, and treat yourself to sweeping views of the Blue Ridge Mountains.
Farmville
The town of Farmville, established in 1798, melds small-town charm with a vibrant college-town vibe. Located 70 miles south of Charlottesville and 150 miles from Washington, D.C., Farmville is home to both Hampden-Sydney College and Longwood University, the latter of which hosted the 2016 Vice Presidential Debate. High Bridge Trail State Park, ideal for horseback riding, bicycling, and hiking, encompasses a 32-mile trail that runs through Downtown Farmville. At more than 2,400 feet long and 125 feet above the Appomattox River, High Bridge is the longest recreational bridge in Virginia and among the longest in the United States.
Appomattox Court House National Historical Park marks the site of the original village of Appomattox Court House, where Generals Ulysses S. Grant and Robert E. Lee negotiated the terms of surrender, effectively ending the Civil War. Farmville’s quaint downtown Main Street area has shops selling everything from furniture to women’s clothing and accessories. A fabulous choice for lodging is Hotel Weyanoke, offering elegant accommodations, a delightfully cozy restaurant, and top-notch service.
Winchester
Founded in 1744 by Colonel James Wood, Winchester is the oldest city in Virginia west of the Blue Ridge Mountains. George Washington made his first trip to Winchester at age sixteen as a land surveyor. Washington built Fort Loudoun during the French and Indian War and, at twenty-six, was elected to his first public office as the county’s representative to the House of Burgesses. Interestingly, a central water system was installed in Winchester in 1808, making it one of the earliest public water systems in the U.S.
For more history, explore regional art at the Museum of the Shenandoah Valley or interactive exhibits for all ages at the Shenandoah Valley Discovery Museum. Winchester has long been known as the Apple Capital as vast orchards surround it and it represents one of the largest apple export markets in the country. Its annual spring event, the Shenandoah Apple Blossom Festival, draws over 250,000 people each year. Perfect for a weekend retreat, the stately Georgian Revival George Washington Hotel includes a fitness center, business center, pool, and spa.
Venture To These Tranquil Virginia Towns
These serene Virginia towns combine history, charm, and relaxation for the perfect weekend retreat. From museums and historic sites to vineyards and trails, each town provides unique experiences for every taste. Whether you're soaking in the rich history of Charlottesville or delighting in the peaceful ambiance of Middleburg, these destinations promise rejuvenating, memorable getaways. So skip the large cities and discover the many spectacular gems that Virginia has to offer!
