12 Perfect Destinations For A Long Weekend In Virginia in 2026
One of the first regions of the United States to be settled by Europeans way back in the 1600s, Virginia today offers no end of charming old towns that make for ideal weekend getaways. Williamsburg is sure to impress if you love colonial history, with its remarkably preserved streets and immersive living-history experiences. For a different kind of escape, Luray is just as appealing for nature lovers, thanks to its famous caverns and easy access to the stunning scenery of Shenandoah National Park. Better yet, no matter what time of year you visit, you’ll find no shortage of fun things to do in these quaint Virginia communities. From sites frequented by the country’s Founding Fathers to Revolutionary and Civil War battlefields, these 12 towns offer a rewarding blend of culture, relaxation, and adventure.
Winchester
Winchester is a hub for history buffs and is well-known for its pivotal role in the Civil War. Founded in 1744 in the beautiful Shenandoah Valley, an area dubbed the region’s “breadbasket” during the conflict, there are plenty of fun things to do in Winchester for those spending a long weekend here. The Museum of the Shenandoah Valley is a great place to start exploring and features exhibits on regional art and history, as well as magnificent grounds. The museum’s Glen Burnie House and Gardens is especially lovely, so take your time and enjoy its peaceful setting.
When booking accommodations, try to stay as close to Old Town Winchester as possible. I loved my stay at the charming George Washington Hotel, just a block away from this lively, pedestrian-friendly area filled with unique boutique shops and tasty restaurants like the Union Jack Pub & Restaurant, which offers a delightful British-inspired menu. From here, it's easy to walk to several must-see attractions such as Stonewall Jackson’s Headquarters Museum, where you can see artifacts from the Confederate general’s campaigns, and George Washington's Office, where the future president managed local fortifications. For outdoor enthusiasts, Abrams Creek Wetlands Preserve is perfect for exploring trails and birdwatching among over 200 acres of protected wetlands, offering a peaceful escape into nature.
Charlottesville
Deservedly ranked as Virginia’s top college town as it’s home to the University of Virginia (UVA), Charlottesville is one of the best places to visit for a weekend getaway. I thoroughly recommend a stay at the wonderful Oakhurst Inn, a historic 4-star property with elegant rooms, a swimming pool, the lively Château Lobby Bar (check out their “Gin and Jazz” nights), and a café, all set around a quiet village-green setting just a few minutes walk from UVA’s spectacular Lawn. A UNESCO World Heritage Site, the Lawn is a must-see and a wonderful place to spend a few hours, especially if you include the famous Rotunda.
In addition to establishing UVA, Thomas Jefferson also designed and built his spectacular Monticello residence. Set on a hill a few miles from the university, Jefferson’s plantation is a must-visit and can be explored as part of a guided tour. Afterwards, you can wander the grounds and the interesting David M. Rubenstein Visitor Center to learn more about the estate and the man behind it. Finally, be sure to visit Charlottesville’s Downtown Mall, one of the longest pedestrian malls in the country. Boasting over 120 shops, galleries, and restaurants, including the first-rate C&O, serving up great “New American” grub since 1976.
Lexington
Historic Lexington is perfect for those seeking a couples' weekend retreat. And it doesn’t get much more romantic than taking a horse and carriage ride around this lovely old town. The Lexington Carriage Company provides a comfy horse-drawn ride about town, with knowledgeable guides pointing out all the best sites with fascinating tidbits of info, making it a truly immersive experience. Hour-long tours start at the Lexington Visitor Center and take in Washington and Lee University, the Virginia Military Institute, and the Stonewall Jackson House. After the tour finished, I knew exactly where to go when exploring this very walkable town on foot.
A wonderful opportunity to explore is during the Lexington Historic House Tour each summer, when many charming 19th-century homes open their doors to visitors. Looking for a place to stay? The charming Gin Hotel, over 100 years old, is right in the heart of Old Town, just a short walk from most attractions. Plus, it features a lovely restaurant in the Juniper Lounge—try to snag a table on the patio overlooking Main Street for a truly delightful experience.
Williamsburg
There’s no place better to get a taste of old colonial Virginia than Williamsburg. Settled by the English in 1632 and the Virginia capital from 1699 to 1780, the highlight here is Colonial Williamsburg, a sprawling site that stretches for a mile from the original Capitol building to the College of William & Mary, with countless well-preserved and reconstructed colonial buildings in between. The world’s largest living history museum, it’s so big you’ll need at least a long weekend to see everything.
I had a wonderful three-night stay in one of the Williamsburg Inn’s charming Colonial Houses, a lovely former forge and kitchen that’s been transformed into a cozy vacation cottage. Dating back to the late 1700s, it’s just a short walk to wonderful attractions like the Governor’s Palace, where guided tours reveal its stunning interior, and the DeWitt Wallace Decorative Arts Museum, home to an impressive collection of period furniture and ceramics. The experience is just as delightful in winter, especially during December’s Williamsburg’s Grand Illumination, where fireworks, musical performances, and candlelit tours create a magical atmosphere.
Luray
Luray, famous for the stunning Luray Caverns, is a truly enchanting destination nestled in the heart of the Shenandoah Valley. Since its discovery in 1878, it's become one of Virginia’s most beloved attractions. Visitors can enjoy a fascinating 1.25-mile underground walk through spectacular sights like stalactites, stalagmites, and the amazing Great Stalacpipe Organ, a unique instrument that creates musical sounds by striking rock formations. To make the most of your visit, plan to spend most of the day exploring both the underground wonders and above-ground attractions, including the Car and Carriage Caravan Museum, Toy Town Junction, and the Luray Valley Museum.
Head into town and you’ll pass the Luray Singing Tower with its magical Carillion, as well as one of the best hotels in Luray, the historic Mimslyn Inn. Set atop a hill on the edge of town, this majestic hotel is a great place for those seeking a romantic weekend away. It also makes for a great base from which to explore Shenandoah National Park.
Fredericksburg
Steeped in Revolutionary and Civil War history, Fredericksburg is a great small town to spend a weekend. Historic highlights include the Fredericksburg & Spotsylvania National Military Park, which preserves the sites where four important Civil War battles were fought, including those around the Chancellorsville and Spotsylvania Court House. You’ll also want to visit the James Monroe Museum and Memorial Library, located in a building once owned by the fifth U.S. president. For a change of pace, stroll along Caroline Street, lined with eateries like Foode, which serves seasonal dishes in an 1820s building.
Events like the Fredericksburg Fine Arts Show in March, where you can enjoy beautiful works from local artists, and the festive Holiday Candlelight Tour in December are wonderful reasons to visit during the cooler months. For a cozy stay, the Courtyard Fredericksburg Historic District offers spacious rooms and a lovely on-site bistro, making you feel right at home. Alternatively, the Kenmore Inn provides charming historic bed-and-breakfast accommodations with period furnishings and delicious gourmet breakfasts, all within easy walking distance to Fredericksburg's best sights.
Petersburg
Located just a short drive south of Richmond, the state capital, Petersburg also played a significant role in the Civil War, with the Petersburg National Battlefield preserving the site of the longest military event of the war. Pay a visit and you can take a self-guided tour to learn about the 292-day siege that culminated in the Union’s victory. Other must-visits here include the Centre Hill Mansion Museum with its fascinating glimpse into 19th-century life (guided tours are available), and the Blandford Church, completed in 1737 and featuring 15 stained-glass windows designed by Louis Comfort Tiffany.
The recently re-opened Hotel Petersburg makes for a wonderful weekend getaway. Originally built in 1916 and recently refreshed with a multi-million dollar renovation, it’s a short, pleasant walk to charming attractions in Historic Old Towne Petersburg. You can explore the lively City Market building from 1878, still bustling today, or visit the beautifully preserved Historic Farmers Bank Museum from 1812. Don’t forget to indulge in a delightful British afternoon tea at the charming Blue Willow Tearoom for a truly special treat.
Front Royal
As the gateway to Shenandoah National Park and the breathtaking Skyline Drive, Front Royal is a perfect starting point for your weekend of adventure. Begin your journey at the friendly Front Royal/Warren County Visitors Center, located in a charming historic railway station right in the heart of the vibrant downtown. Here, you'll find helpful maps for hiking and scenic drives, along with information about local attractions like the intriguing Belle Boyd Cottage, once home to the renowned Confederate spy, and the Warren Rifles Confederate Museum, where you can explore fascinating Civil War artifacts.
In addition to its boutique shops and eateries, downtown Front Royal is a great place to visit if you enjoy great beer. My favorites included Vibrassa Beer and the wonderful Virginia Beer Museum with its displays, artifacts… and memorable brews. Accommodation options include the affordable Blue Ridge Motel and the Hampton Inn Front Royal with its comfortable rooms and modern amenities.
Wytheville
Situated in the southwest corner of Virginia and easily accessible via I-77 and I-81, Wytheville was one of those places I often hurried past on my way to South Carolina and Florida. However, my wife and I decided to break that pattern and enjoy a delightful weekend exploring Wytheville. We were drawn by the chance to discover more about this charming town’s meaningful link to Edith Wilson, one of the country’s most beloved First Ladies.
Highlights included visiting the Edith Bolling Wilson Birthplace Museum with its impressive collection of artifacts that once belonged to the wife of President Woodrow Wilson and staying at the delightful Bolling Wilson Hotel located across the road from the museum. Built in 1927, a stay in this lovely old hotel is like stepping back in time. Other fun things to do in Wytheville include visiting the Haller-Gibboney Rock House, a museum dedicated to 19th-century frontier life, and the nearby Big Walker with its 100-foot tall observation tower overlooking the Appalachian Mountains.
Strasburg
Strasburg’s another Shenandoah Valley town that’s worth considering for a Virginia long weekend getaway. This quaint old town is a popular shopping spot, especially for antique enthusiasts. If that sounds like you, include the Strasburg Emporium on your must-visit list. This sprawling marketplace covers 52,000 square feet and is home to over 60 vendors, so you’re guaranteed to find something worth taking home. The Strasburg Museum is another must-visit for its exhibits on pottery, textiles, and Civil War artifacts.
A wonderful time to visit is during the Strasburg Harvest Festival each fall, where you can enjoy local crafts, delicious food vendors, and lively music. For a comfortable overnight stay, consider the charming Hotel Strasburg, nestled in a beautifully restored Victorian-era building right in the heart of downtown, or the welcoming Fairfield Inn & Suites by Marriott.
Staunton
Another town with a connection to Woodrow Wilson, Staunton, is a popular spot to visit for its well-preserved downtown area and cultural attractions. Topping your list of places to visit while here for a weekend should be the American Shakespeare Center’s Blackfriars Playhouse, the world’s only recreation of Shakespeare’s indoor theater offering year-round theatrical productions. The town’s presidential connection stems from Staunton being the place where Woodrow Wilson was born in 1856, a fact that’s celebrated at the Woodrow Wilson Presidential Library and Museum. Here, you’ll enjoy a comprehensive look at the life of the 28th President, with exhibits on his presidency, early life, and World War I.
Staunton also welcomes you to the Queen City Mischief and Magic Festival, a delightful event in September that turns the town into a magical celebration inspired by all things Harry Potter. Enjoy themed activities, browse charming vendors, and be entertained by various shows. Whether you’re here for this enchanting festival or simply exploring, you'll find great places to stay, like the Blackburn Inn—a charming boutique hotel housed in a historic building from 1828—or the Frederick House, which offers warm, cozy accommodations just a short walk from downtown. It’s truly a charming spot to experience!”,
Bedford
Bedford is a great weekend getaway destination for history fans and military buffs. Located near the Blue Ridge Mountains, this small town is home to the National D-Day Memorial, a moving tribute to the sacrifices made by WW2 Allied forces on June 6, 1944. In addition to its displays and moving tributes to the personnel involved, the sprawling grounds also feature walking trails and plenty of benches.
Downtown has some real gems like the Bedford Museum and Genealogical Library, where you can dive into the town’s rich history. There are also lots of charming places to eat and shop. If you’re visiting in September, the Bedford Centerfest is a wonderful event filled with local artisans, musicians, and tasty food vendors — a perfect time to experience the community’s spirit. For a cozy stay, the Peaks of Otter Lodge offers lovely lakeside rooms with beautiful mountain views that truly make your visit special.
The Final Word
As anyone who has ever visited Virginia will admit, the state’s small towns are treasure troves of history and culture and offer no end of fun experiences for weekend getaways. From the caves of Luray to the historic streets of towns like Fredericksburg, each of these lovely destinations provides opportunities to explore and, most importantly, kick back and relax. With comfortable accommodations and unique attractions in each of these destinations, you’ll find something to enjoy, no matter your interests. Yes, indeed, these 12 perfect destinations for a long weekend in Virginia are just that… perfect. For more tips and tactics, check out the Visit Virginia website.
