12 Perfect Destinations For A Long Weekend In Virginia
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. From picturesque historical hubs to scenic mountain retreats, each destination has its own unique character with plentiful attractions, festivals, and landmarks to explore. Whatever time of year you visit, you’ll find no end 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 destinations today provide a fun blend of culture, relaxation, and adventure. I recently had the good fortune to visit these wonderful small towns in the “Old Dominion” and am excited to share a little of what makes each of them the perfect destination for a long weekend in Virginia.
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 get as close to Old Town Winchester as possible. I enjoyed a stay at the historic George Washington Hotel, literally only a block from this fantastic pedestrian-friendly are with its boutique shops and restaurants such as the Union Jack Pub & Restaurant, a classic British-inspired eatery. From here you can also easily walk to attractions such as Stonewall Jackson’s Headquarters Museum, where artifacts from the Confederate general’s campaigns are displayed; and George Washington's Office, where the future president oversaw the construction of local fortifications. For outdoor lovers, Abrams Creek Wetlands Preserve offers trails and birdwatching opportunities with over 200 acres of protected wetlands to explore.
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 great time to visit is during the Lexington Historic House Tour, held each summer when numerous 19th-century homes throw open their doors to the public. Where to stay? The 100-plus-year-old Gin Hotel is located in the heart of the historic Old Town just a few minutes’ walk from most attractions and even has a great restaurant in the Juniper Lounge (opt for a table on the patio overlooking Main Street).
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 enjoyed a three-night stay in one of the Williamsburg Inn’s excellent Colonial Houses, a former forge and kitchen converted into an elegant vacation cottage. Built in the late 1700s, you’ll be just steps from attractions like the Governor’s Palace, which offers guided tours of its ornate interior, and the DeWitt Wallace Decorative Arts Museum with its vast collection of period furniture and ceramics. It’s equally pleasant in winter when events like December’s Williamsburg’s Grand Illumination features fireworks, musical performances, and candlelit tours.
Luray
Best known for the spectacular Luray Caverns, Luray is a must-visit destination in the heart of the Shenandoah Valley. Discovered in 1878 and one of Virginia’s top attractions, you can wander a 1.25-mile underground pathway through breathtaking landscapes including stalactites, stalagmites, and the fantastic Great Stalacpipe Organ, an instrument that produces musical tones by striking rock formations. Expect to spend the best part of a day here if you also take in above-ground sights such as 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 include the Fredericksburg Fine Arts Show in March, showcasing works from regional artists, and the Holiday Candlelight Tour in December are great excuses to visit in the cooler months. As for accommodations, the Courtyard Fredericksburg Historic District features spacious rooms and an on-site bistro, while the Kenmore Inn is a historic bed-and-breakfast offering period furnishings and gourmet breakfasts within walking distance to the best sightseeing in Fredericksburg.
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 is a great option for a weekend stay. Built in 1916 and fresh from a multi-million dollar renovation, it’s an easy walk from here to other highlights of Historic Old Towne Petersburg including the City Market building, constructed in 1878 and still in use today; and the Historic Farmers Bank Museum dating from 1812 and perfectly preserved. And be sure to treat yourself to an authentic British afternoon tea at the delightful Bue Willow Tearoom.
Front Royal
As the gateway to Shenandoah National Park and the spectacular Skyline Drive, Front Royal makes an ideal base for those wanting to spend a weekend of exploration. Start your adventure at the Front Royal/Warren County Visitors Center. Set in a former railway station in the heart of the picturesque downtown area. Here, you can pick up materials, including maps for hiking and scenic drives, as well as details of attractions, including the Belle Boyd Cottage, home to the infamous Confederate spy, and the Warren Rifles Confederate Museum, which houses artifacts from the Civil War.
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
Located in the southwest corner of Virginia and easy to get to via the I-77 and I-81 highways, Wytheville was a place I all too often whizzed past while heading to South Carolina and Florida. My wife and I finally put paid to that bad habit and spent a fun weekend exploring Wytheville, lured by the promise of learning more about this lovely town’s deep connection to one of the country’s best-loved First Ladies, Edith Wilson.
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 great time to visit is during the Strasburg Harvest Festival each fall, with local crafts, food vendors, and live music. Top picks for an overnight stay include the cozy Hotel Strasburg, housed in a restored Victorian-era building in the heart of the downtown area, and the 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 is also home to the Queen City Mischief and Magic Festival, a fun event held in September that transforms the town into a celebration of all things Harry Potter with themed activities, vendors, and entertainment. Whether you’re visiting during this quirky event or not, popular places to stay in Staunton include the Blackburn Inn, a boutique hotel housed in a historic property built in 1828, or the Frederick House, offering cozy accommodations with a personal touch and just a stroll away from downtown.
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 highlights include the Bedford Museum and Genealogical Library, which provides insight into the town’s history, as well as plenty of dining and shopping experiences. Bedford Centerfest in September is a great time to visit and features local artisans, musicians, and food vendors. For accommodations, the Peaks of Otter Lodge offers lakeside rooms with mountain views.
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.
