Virginia's 9 Most Festive Downtowns For The Holidays

Virginia’s small towns have a way of making the holidays feel handmade. Across the state, classic downtowns glow with lights, wreaths, and welcoming shop windows. From the Shenandoah Valley to Hampton Roads, these destinations offer an ideal mix of history, hospitality, and holiday cheer in November and December 2025. Whether you crave a tree-lighting ceremony, a festive market, or an evening stroll under twinkling lights, these nine Virginia towns capture the spirit of the holidays in timeless style.

Ashland

Just north of Richmond, Ashland combines rail-town nostalgia with spirited celebration. The highlight of the 2025 holiday season is Light Up the Tracks on November 22, when more than 10,000 lights illuminate the downtown corridor through the end of December. After the ceremony, explore Thompson Street and Railroad Avenue, where boutiques and galleries decorate their windows in glowing displays.

Visitors can cap the evening with carriage rides or hot chocolate from one of the local cafés. The next day, the 56th annual Olde Time Holiday Parade fills downtown alongside a festive vendor market. Ashland’s mix of train whistles, bright lights, and small-town hospitality makes it one of Virginia’s most heartwarming holiday destinations.

Middleburg

Set amid horse country in Loudoun County, Middleburg delivers a holiday experience that feels straight from a storybook. The early-December Christmas in Middleburg Parade brings horses, hounds, and antique carriages through the heart of downtown, followed by the tree-lighting that signals the start of the season.

Shoppers can wander South Madison Street, lined with boutiques, galleries, and cafés adorned in holiday décor. Another favorite event, Jingle in the Burg, fills the town with live music, food trucks, and festive cheer in mid-December. Families can also enjoy Breakfast with Santa at the local charter school. Middleburg’s elegant atmosphere and deep traditions make it one of Virginia’s most photogenic and festive winter retreats.

Culpeper

Located in the heart of the Piedmont, Culpeper’s downtown celebrates the holidays with classic style. The annual Culpeper Christmas Parade, held in 2025 on December 7, features illuminated floats, marching bands, and plenty of small-town enthusiasm. The parade is preceded by the popular Holiday Sunday Funday for Kids, with crafts, vendors, and visits with Santa for families.

Between events, stroll Davis Street, where historic brick buildings house boutiques, chocolatiers, and restaurants serving seasonal specials. The 1930s-era State Theatre often hosts holiday events and performances, adding a touch of history to your visit. Culpeper’s combination of lively events, historic charm, and cozy dining makes it a perfect stop for an old-fashioned December getaway.

Christiansburg

Set in Virginia’s New River Valley, Christiansburg welcomes the holidays with warmth and tradition. Christmas on Main on December 12, 2025, features a parade, local vendor market, and the town’s tree lighting to start the season.

All throughout the holidays, the shops and restaurants on Main Street host festive promotions, while pop-up vendors line the sidewalks. Visitors can also enjoy the festive decor and great food at restaurants such as The Farmhouse, a local favorite. With its friendly pace and cheerful streetscape, Christiansburg turns a December evening into a charming small-town memory.

Staunton

Staunton’s cobblestone streets and Victorian architecture create an enchanting holiday atmosphere in the picturesque Shenandoah Valley. The downtown centerpiece is Beverley Street, where window displays and holiday lights glow from historic façades. Visitors can take in seasonal performances at the American Shakespeare Center, a 17th-century-style theater that is staging A Christmas Carol throughout December 2025.

Nearby Gypsy Hill Park transforms into a wonderland of illumination during the Celebration of Holiday Lights, with the 2025 edition running from November 24 through New Year’s Day. Staunton’s graceful mix of architecture, art, and winter charm makes it a shining jewel of Virginia’s holiday season.

Smithfield

On the banks of the Pagan River, Smithfield’s historic downtown combines colonial character with a welcoming holiday spirit. Held this year on December 6-7, the 2025 edition of Christmas in Smithfield offers landmark tours, an antique show, and a holiday market. The following weekend, the annual Smithfield Christmas Parade fills downtown with floats, marching bands, and festive lights. Alongside the parade, visitors can explore the revitalized Main Street, home to local shops and boutiques offering handcrafted gifts. Afterward, enjoy a meal at Taste of Smithfield, a restaurant celebrating the town’s famous ham heritage. With its rich history and close-knit community, Smithfield offers a holiday experience filled with warmth, charm, and genuine small-town pride.

Dayton

The Shenandoah Valley village of Dayton is small but full of festive energy. The 2025 seasonal festivities begin with Small Town Christmas on November 28, followed by the Dayton Christmas Parade and Tree Lighting on December 5. Downtown’s quaint streets are the focus, as local businesses join in a friendly Holiday Decorating Contest that fills the storefronts with sparkle. Visitors can also browse handcrafted gifts at the Dayton Market Christmas Open House on December 6. Between events, take a stroll through downtown Dayton’s cozy and picturesque business district, where cafés and antique markets make ideal stops for warming up and shopping local.

Abingdon

Southwest Virginia’s Abingdon pairs its rich arts culture with small-town holiday charm. The town likens itself to a southern ‘It’s a Wonderful Life,’ its classic architecture adorned with holiday decor, a look highlighted during events like the annual Merchant Open House on November 22, 2025.

Visitors can attend festive productions at the Barter Theatre, one of the nation’s oldest playhouses, or browse gifts at the Heartwood Artisan Center, showcasing regional crafts. Afterward, stop by one of the Main Street restaurants for a warm, locally sourced meal. With its Appalachian setting, creative flair, and cozy winter ambiance, Abingdon exudes an inviting blend of tradition and artistry.

Lexington

Rich in history and college-town charm, Lexington becomes a winter wonderland each December. The 2025 festive season officially begins with the Candlelight Processional and Tree Lighting on November 28, when residents gather downtown for carols and candlelit cheer. The following weekend, the Lexington Christmas Parade winds through Main Street, framed by stately 19th-century buildings.

Between events, visitors can explore the Stonewall Jackson House Museum or browse the elegant Main Street boutiques, which stay open late for holiday shopping. Many locals and visitors choose to finish the day with a meal at Hardens Restaurant, a family-owned local favorite. Lexington’s blend of heritage and warmth makes it a highlight of Virginia’s holiday circuit.

A Season Wrapped in Small-Town Cheer

Virginia’s festive downtowns remind travelers that the holidays are best enjoyed slowly, among familiar streets and friendly faces. From the rail-lit glow of Ashland to the candlelit charm of Lexington, each town offers its own way to celebrate community and tradition during the holiday season. These are places where carolers sing by shop windows, floats glide past, and neighbors share genuine holiday greetings. Whether you come for a weekend or simply for an evening stroll, Virginia’s small towns promise a holiday experience that feels authentic, welcoming, and beautifully timeless.