Frozen trees on a lake in Williamsburg, Virginia.

These Towns in Virginia Come Alive in Winter

Often when people think of visiting Virginia, planning a visit to the state in the winter season does not come to mind. However, a trip to the state's lovely small towns during this time of year, visitors will be pleasantly surprised by their charming winter allure. Cute towns such as Fredericksburg have their historic downtowns decorated for the holidays, making landmarks such as George Washington's boyhood home extra magical. Winchester has an Old Time Winter village with activities over the holiday season, such as caroling and carriage rides. There are also outdoor activities aplenty to enjoy, such as skiing in Staunton. Whether visitors are looking for low-key holidays replete with outdoor winter fun, there is no better place than these small Virginian towns! 

 Staunton

Downtown historic Staunton, birthplace of President Woodrow Wilson
Downtown historic Staunton is the birthplace of President Woodrow Wilson. Image credit MargJohnsonVA via Shutterstock.

One of the most beautiful towns to visit in winter is Staunton. The town is in the heart of Virginia, offering stunning mountain views. Enjoy the snow-dusted mountain vistas from Montgomery Hall Park, Betsy Bell, and Mary Gray Wilderness if you do not mind getting muddy. The parks have plenty of trails to explore as well. Another great way to enjoy the views in winter is by hitting the slopes and skiing. 

Afterward, relax and enjoy walking around Saunton's downtown. The downtown received a "Great American Main Street Award," and while meandering Staunton's streets, it is easy to see why. The compact downtown has over 100 unique shops, galleries, and restaurants.  There is also a historic district to explore. Get cozy inside and watch a play at the Blackfriars Playhouse or tour the Woodrow Wilson Presidential Library and Museum. Staunton is a magical Virginia winter town from outdoor fun to a cozy downtown.

Fredericksburg

Falmouth Bridge in Fredericksburg, VA
Falmouth Bridge in Fredericksburg, VA.

The historic town of Fredericksburg embraces holiday magic in wintertime. The downtown has several historic buildings and museums to explore the town's history, including the Hugh Mercer Apothecary Shop, Mary Washington House, and the Rising Sun Tavern. Travelers can also tour George Washington's boyhood home at Ferry Farms. To enjoy some of the town's nature, check out the Heritage Trail. The 3.1-mile loop connects two previous trails and takes you through the heart of downtown, along the river and Old Mill Park. In the winter, the snow-covered trail makes for the perfect stroll. 

During the holiday season, check out some of the annual events the town puts on. The Fredericksburg Christmas Market and holiday parade downtown are the perfect festivities to kick off your holiday season. 

Williamsburg

Frozen trees on lake in Williamsburg, Virginia.
Frozen trees on a lake in Williamsburg, Virginia.

Another Virginia town known for its winter festivities is Williamsburg, featuring everything from historic traditions to magical Christmas lights. During winter, the Busch Gardens theme park becomes a Christmas Town. The theme park displays over ten million twinkling lights, making it one of the largest light displays in North America: christmas-themed treats, a Christmas Town Express, and Santa’s Workshop. 

Check out Williamsburg's Jamestown settlement if you prefer historical Christmas displays to theme parks. The historical site has a rich history dating back to the early 1600s when the first European settlers arrived. In December, Jamestown decorates the town in period-accurate Christmas décor. Visitors can learn about past festivities that took place on Christmas.

Another festive favorite in Williamsburg is the Lighted Boat Parade. The parade is in Yorktown and features boats covered in Christmas lights passing by the waterfront. There is also live music, hot cider, and Christmas carolers. After seeing Williamsburg's winter festivities, check out the historic Shields Tavern. The 18th-century tavern has delicious food, live music, and an inviting atmosphere.

Charlottesville

The Fresh snowfall on the University of Virginia grounds The Rotunda featured in the center
Fresh snowfall on the University of Virginia's campus in Charlottesville. Image credit Wirestock Creators via Shutterstock.

During winter, Charlottesville becomes a winter wonderland. From festive gardens to a magical open-air market, there is something for all in Charlottesville.  A popular spot in town to explore is Thomas Jefferson's gardens, called the Monticello. In winter, the gardens have special evening tours showing off the holiday-themed decor and honoring Jefferson-era traditions. Once you have visited the beautiful gardens, check out the nearby Charlottesville City Market. This is the area's oldest open-air market. You can find seasonal produce and baked goods here sold throughout the year. A special event to check out is Winter Wander at Boar's Head. This is a walking trail in town that makes for a magical outing. The course is lit up from mid-November until early January, revealing whimsical holiday decorations and themes. 

Monterey

Fair Lawn Farm maple syrup agriculture small business sign
Fair Lawn Farm sign is a small maple syrup business in Monterey. Image credit Kristina Blokhin via AdobeStock.

Monterey is one of the smallest towns on this list, with 147 people. However, while it may be small, it is home to some of Virginia's most stunning countryside views and the Blue Ridge Mountains. Snow covers the town's ground in winter, making the pictures more spectacular. To enjoy winter in Monterey, walk around town, enjoy the scenery, and learn about some history. Visiting the Highland County Museum can be a nice escape from the cold.

If you love arts and crafts, you will want to follow the path of Monterey's Barn Quilt Trail. This includes around three dozen quilts painted on boards and mounted to barns, homes, and other buildings around the county. Once you've seen the trail, snuggle up in an authentic log cabin at the Cabin at Faraway Farm. The house has a queen bedroom and two twin beds in the loft. It's the perfect stay for your winter vacation.

Winchester

Winchester Historic District North Washington street sign seen during a sunny winter late afternoon
Winchester Historic District North Washington street sign seen during a sunny winter late afternoon.

A Virginia town known for its European vibe and Christmas festivities is Winchester. Every year, the historic town holds an Old Time Winter Village. The cozy festival occurs in the heart of the Old Town pedestrian mall. The shops all have special offers during this time. There are also complimentary horse-drawn wagon rides for visitors. Walking around the area, you will probably hear carolers or Christmas music. Grab a warm glass of gluhwein from a participating restaurant to enjoy the festivities. This delicious drink is a hot, mulled, spiced red wine. If you want to get in the holiday spirit, Winchester is the place to be!

Culpeper

Downtown Street in Culpeper, Virginia
Downtown Street in Culpeper, Virginia. Image credit refrina via Shutterstock.

An unsuspecting stunning town to visit in winter is Culpeper. The small Northern Virginian community possesses an unparalleled small-town charm. The city holds a winter farmers' market downtown during the winter months. The market vendors sell everything from produce, baked goods, and horticultural products to handcrafted artisan goods. Yowell Meadow Park is a  popular spot in town to enjoy the outdoor winter scenery. The accessible park is in Downtown Culpeper and has a paved walking trail. The one-mile path has signs explaining the town's history and si the perfect stroll for everyone to enjoy. If you want to explore more of Culpeper's winter magic, stay at the Manor House at Spring Haven Farm. The house is set up like an old English Hunting Lodge with 10-foot beamed ceilings and massive stone fireplaces to cozy up to.

Virginia's small towns are an unsuspecting winter treasure. Visitors can expect to find snow-covered mountains, quaint winter markets, unique holiday festivities, and cozy cabins. Towns such as Staunton showcase the stunning beauty of the Shenandoah Valley, covered in snow. Enjoy a charming open-air market in Charlottesville. Finish enjoying Virginia's small towns by cozying up in an authentic log cabin in Monterey. For anyone looking for a winter getaway, any of these small towns will make for the perfect trip!

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