11 Autumn-Ready Virginia Towns For A Weekend Retreat

Virginia is a beautiful place to visit at any time of year. Autumn, however, transforms the “Old Dominion” into an unforgettable, somewhat magical travel destination. Dense forests and tree-lined streets alike become even more appealing as maple, oak, and hickory trees add a backdrop of crimson, gold, and burnt orange to an already attractive landscape.

This incredible autumnal eye-candy all adds up to making Virginia one of the Mid-Atlantic region's top places for leaf-peepers to visit for a fall weekend escape. Better still, the state’s unique microclimates give it one of the country’s longest peak foliage seasons, extending from early October through to mid-November. So, whether you’re looking for a quiet coastal break or an excuse to explore the beautiful Blue Ridge Mountains, here are 11 autumn-ready Virginia towns I’ve visited that are just perfect for a weekend retreat.

Wytheville

Wytheville was a destination I all too often drove past on my way to places like Hilton Head and Orlando. That all changed when I recently stopped for a few days to explore the town and its surrounds. Long a hub for travelers heading south along Route 21 (aka, the Great Lakes to Florida Highway), its location on Interstates 77 and 81 is a good reason to stop and explore, rather than simply speed past.

Base yourself at the downtown Bolling Wilson Hotel. Named after the former first lady (and the subject of the Edith Bolling Wilson Birthplace Museum directly across the road), this 1920s property also boasts an excellent restaurant, Graze. Afterwards, pop up to the Rooftop Terrace for its splendid fall views over both the town and the surrounding Blue Mountains. From here, it’s a five-minute drive to the Wohlfahrt Haus Dinner Theatre with its Broadway-quality professional productions… and great food.

Another great option for a weekend getaway is the Eupepsia Wellness Center, a luxurious facility that offers three-day (and longer) health and wellness retreats, along with spa treatments and delicious vegetarian meals. While you could get to Eupepsia in 20 minutes via the highway, take the slow drive through along the Big Walker Mountain Scenic Byway. This 16-mile stretch of the old Florida road passes Big Walker Lookout, a 100-foot observation tower that provides spectacular fall views across five states, as well as a quirky general store (be sure to try their ice cream).

Danville

It’s not for noDanville City of Churches photo Bryan Dearsleything that the former tobacco and textile town of Danville is known as the City of Churches. Boasting one of the highest densities of churches in the country, wander up Millionaire's Row to see some of the best, along with many restored Victorian and Edwardian mansions. While self-guided walking tours of this picturesque street are available, I opted for a guided tour led by the awesome Joyce Wilburn, as it included a look inside one of these classic mansions (ask nicely, and you may even get to take a peek inside one of Danville's pretty churches).

The River District is another great place for a stroll. Follow the Riverwalk Trail from the Main Street Plaza along the banks of the Dan River before checking out the converted tobacco warehouses now housing attractions like the Farmers’ Market and the Danville Science Center. This state-of-the-art facility also features the Dome, which, in addition to providing a close-up look of the night sky above Danville, also hosts nature shows and other immersive, wrap-around viewing experiences.

As for accommodations, I thoroughly recommend the boutique Bee Hotel. Set in a restored 1920s newspaper building complete with an original printing press in its lobby, it’s situated directly across the street from Danville City Hall and within walking distance of Main Street, Millionaire’s Row, and those marvellous churches. It’s also a great place to base yourself for the fall Market Monster Mash, which sees the River District and town come alive with Halloween fun.

While you’ll need to drive to it, the superb Schoolfield Restaurant is located directly across the road from the brand new Caesars Virginia. This fine dining establishment offers delicious dishes using local ingredients (ask if the pork chop is on the menu!), as well as a cocktail bar that serves up a delicious Lady Astor, so-named after the first female British MP who was, in fact, born in Danville.

Onancock

The area where the Chesapeake Bay town of Onancock is built is so attractive that Captain John Smith, the first Englishman to set eyes on it, proclaimed it to be “the Gem of the Eastern Shore.” It’s a compliment that stands to this day. Spend a weekend at the cozy Inn at Onancock, a Victorian-era bed and breakfast. In addition to hostess Kim’s incredible homemade breakfasts (try her pancakes!) and the 5 pm “Wine Down” drinks and nibbles, you can easily walk from here to Onancock Wharf and Marina to catch a Bay sunset.

Better still, book a table at Mallards at the Wharf, a classy restaurant known for its fresh local seafood, waterfront setting, and sunset views. For more casual fare and the best bar pizzas on the Eastern Shore, the Onancock Taphouse(or “OT” to those in the know) is steps from the B&B and serves craft beers from the not-too-far-away Cape Charles Brewing Company (their stouts are superb).

The best time to visit? Plan your weekend break around the town’s November Champagne and Oyster Tasting event at the Historic Onancock School. On the way, you’ll walk past Ker Place. Built in 1799, it’s home to the Eastern Shore History Center with exhibits on fishing and oystering, and grounds with plenty of trees to add a dash of color at this time of year.

Bristol

Unique in that the Tennessee-Virginia border slices the town in two along State Street, Bristol is a hopping fall destination that’s famous as the location of the first-ever country music recording. References to these music-altering 1927 recording sessions are seen everywhere across town, with commemorative plaques and attractions celebrating the launch of the careers of early country legends, including Jimmie Rodgers and the Carter Family.

Book a weekend stay at the cool (and aptly named) Sessions Hotel, a complex of 1920s warehouses that now serve as a great base to explore the town. The opulent Bristol Hotel at the other end of the downtown stretch is another good choice and features a rooftop bar that provides views of that famous “Bristol” sign that’s lit up at night.

The real star, though, is the Birthplace of Country Music Museum. Here, fun immersive exhibits show country music's evolution from Appalachian folk traditions through to the famous recording sessions that put Danville on the country music map. You’ll also find no end of events and live music around town, no matter the season, at venues like the Paramount Bristol venue and even the outdoor stage at Sessions Hotel. You can even dine at Southern Craft BBQ Bristol with outdoor seating overlooking the stage and serving double-smoked Burnt Ends… probably the tastiest barbecue dish you’ll ever experience.

Charlottesville

Charlotteville’s magnificent historic landmarks are wonderful to see at any time of year, but fall foliage adds an extra layer of magic. This is especially true at the University of Virginia's historic Academical Village, where Thomas Jefferson's architectural vision, now a UNESCO World Heritage Site, can be explored. Wander across The Lawn toward the magnificent Rotunda, modeled after the Pantheon in Rome, and you’ll stop many times for photos of the treelined pathways, original academic buildings, and old student quarters.

The annual Virginia Film Festival in late October is the perfect excuse to spend a weekend here, as is the opportunity to visit Jefferson’s elegant Monticello estate. Complete your university-town experience with a stay at Oakhurst Inn, a romantic spot spread across two restored buildings dating to 1834 and just a short walk from the UV grounds.

Winchester

The northern entrance to the Shenandoah Valley, Winchester, is perfect for a memorable Virginia weekend getaway. After checking into the George Washington Hotel, head to nearby Old Town Winchester. This pedestrian mall runs four blocks along Loudoun Street and features some of the town’s best eateries (a shout-out to the Union Jack Pub & Restaurant and its tasty fish and chips) and shopping experiences (if art’s your thing, pop into the Eugene B. Smith Gallery).

Old Town is also where you’ll find some of the South’s best-preserved architecture and attractions, such as the Old Court House, home to the Shenandoah Valley Civil War Museum, and George Washington's Office, where the future president spent his early years planning defences against the British. Just a few blocks away, pop into the Handley Regional Library with its beautiful dome, undoubtedly one of the country’s most attractive small-town libraries.

Although you’ll need to drive, the Museum of the Shenandoah Valley is a must-see Winchester attraction. In addition to its vast collections and exhibits relating to Shenandoah history and culture, check out historic Glen Burnie House with its six acres of formal gardens and colorful displays of native plants and trees. When to visit? Plan your weekend around October’s Apple Harvest Festival as the region’s many orchards and cideries demonstrate why Winchester is the “Apple Capital of Virginia.”

Luray

While Luray is an awesome place to visit any time of year, thanks to the incredible Luray Caverns, autumn is especially rewarding as it serves as the perfect jumping-off point to explore Virginia’s wonderful Skyline Drive. Part of Shenandoah National Park, this leaf-peeping paradise stretches north and south from Luray, presenting countless opportunities to enjoy nature’s symphony of colors.

While the leaves peak here mid-October, arriving at the end of leaf-peeping season later in the month and into early November still present plenty of lovely views… and less traffic (though still arrive early to avoid line-ups).

To top your experience, you won’t do better than booking a stay at Mimslyn Inn. Set on a hillside on the outskirts of this small town, it was built in 1931 and is so pretty that it has become one of Virginia’s top wedding destinations. If you’re not planning a summer marriage or anniversary, visit during the Page County Heritage Festival. Held in mid-October when the foliage in the surrounding mountains is peaking, this fun event at Luray’s Page County Fairgrounds features everything from family rides to historic steam-driven tractors.

Williamsburg

A perennial favorite weekend getaway in Virginia, Colonial Williamsburg is the world’s biggest living history museum. And it’s certainly impressive in scale. Set on over 300 acres and home to 89 original structures (plus hundreds of reconstructed buildings), a weekend is the minimum amount of time you should allocate to exploring. Plan to stay at the opulent Williamsburg Inn or one of its several colonial houses, each of which is just steps away from Duke of Gloucester Street, the attraction’s main drag.

As you wander, you’ll meet costumed interpreters demonstrating trades including blacksmithing at Anderson's Forge, bookbinding at the Printing Office, as well as tailoring and dressmaking. Book a tour of the Governor's Palace, rebuilt on its original foundation, and explore its formal gardens with period plantings and intricate topiary. And see all those white gates and picket fences? They’re not there to keep you out. Enter and explore for memorable, quiet, people-free experiences.

Feeling peckish? I thoroughly recommend the fantastic King's Arms Tavern. Established in 1772, you can order authentic 18th-century traditional dishes that are as tasty as they are to learn about. For a more contemporary culinary experience, I thoroughly enjoyed dining at Fat Canary on Merchants Square. And while you could plan your entire experience to coincide with fall events like An Occasion for the Arts in early October, you really could spend a weekend here at any time of year and never run out of fun things to see and do.

Abingdon

The mountain town of Abingdon lays claim to the title of Virginia's first incorporated municipality west of the Blue Ridge. And its history shows, especially in its 20-block historic district with its buildings from the 1770s. Highlights include the Barter Theatre, State Theatre of Virginia, which, in addition to its cultural importance, is also pleasing to look at.

Whether you see a show or not (and you should), the adjacent Martha Washington Inn & Spa is the ideal place to stay to soak up the town’s autumnal ambience. Built in 1832 as a private home and later serving as a women's college and Civil War hospital, be sure to book a carriage ride for a gentle, authentic ride around town. Along the way, you’ll pass The Tavern, which has been around since 1779, and America's oldest continuously operated restaurant is well worth visiting for a meal.

Abington also marks the start of the Virginia Creeper Trail, a 34-mile cycling and hiking path through the national forest and farmland along an abandoned railroad line. Another good excuse for a fall weekend stay is the Virginia Highlands Festival. Although it takes place over two weeks in early August, it’s considered the traditional start of the town’s fall tourism season, with demonstrations of traditional Appalachian crafts at Main Street venues.

Lexington

Horse-drawn carriage tours are also a big thing in Lexington. Departing from the Visitor Center of Lexington, these fun hour-long rides clip-clop past pretty much everything you’ll want to see during your weekend retreat. Afterwards, head back for a stroll through the grounds of Washington and Lee University and the neighboring Virginia Military Institute. This beautiful park-like area features landmarks, including the University Chapel, a historic building that looks even more stunning when the leaves change color.

You’ll want to venture a little further south to see the remarkable Natural Bridge. Located 14 miles south of town, you’ll follow Cedar Creek to this marvel of nature as it rises 215 feet and spans 90 feet above. As for where to stay, check the rates at The Gin Hotel on Main Street. It’s especially lively during the annual Rockbridge Regional Fair in early October at the Virginia Horse Center.

Yorktown

Connected to Williamsburg and Historic Jamestown via the fantastic Colonial National Historical Parkway, Yorktown is revered for its role in the defeat of the British during America’s fight for independence. You can learn about this fascinating period of history at the American Revolution Museum at Yorktown with its reconstruction of a period troop camp and re-enactments, as well as displays about George Washington and the war.

Afterwards, enjoy a stroll to Riverwalk Landing, which actually connects to the museum via a mile-long path that follows the York River. Although a little bit of a hike, the Yorktown Battlefield site preserves the original siege lines and redoubts that were constructed at the time by both sides. Time it right and you can enjoy the Yorktown Day celebration on October 19, 2025, for a commemoration of the British surrender with military reenactments and artillery demonstrations.

For weekend accommodations, The Hornsby House Inn provides quiet stays in a 1930s colonial revival home. It is also conveniently located within walking distance of the battlefield, waterfront, and Yorktown Victory Monument.

The Bottom Line

Virginia Tourism’s excellent and frequently updated Fall Foliage Report is a fantastic resource for those planning on visiting any of these wonderful Virginia destinations for a weekend retreat. I’ve visited each over the course of two fall trips (one in 2024, the other in 2025), and honestly enjoyed each destination so much that, well, I didn’t want to leave. And the state’s extended fall foliage season certainly provides a broad window of opportunity for a memorable stay, whether you choose to spend your time in the mountains or on the coast. And, like me, I bet you won’t want to go home.