The Ultimate Checklist for an Unforgettable Virginia Holiday

Santa isn't the only one making a list and checking it twice! ‘Tis the season for all your favorite holiday fun, and we want to help you make the most out of this time of year.

To make your holiday planning easy, we've compiled a list of ten of our favorite Virginia traditions, affordable activities, and can't-miss winter events. Use our seasonal checklist to fill your days with good cheer, very merry activities, and all the best of the holidays in Virginia! 

1. Visit a Festive Pop-Up Bar

Celebrate the season by visiting one of Virginia's festive pop-up bars, where holiday cheer and craft cocktails come together for a merry good time. These pop-up experiences transform ordinary bars into winter wonderlands, decked out in dazzling holiday decor, twinkling lights, and seasonal vibes. 

From Santa-themed drink menus filled with signature cocktails to glitzy eye-catching holiday decor, there's something for everyone to enjoy. Gather with friends for a fun night out at these pop-up bars, where you can pair tasty food and drinks with live music and festive photo ops.

A Few of Virginia’s Holiday Pop-Ups

• The Forum Hotel’s Chalet Bar–Charlottesville
• The Doyle Hotel’s Elf’d Up–Charlottesville
• Miracle on Cary Street–Richmond
• Birdie’s Evergreen–Richmond 
• Rum & Reindeer at Island Shrimp Company–Richmond 
• Tinsel & Tequila at Casa Del Barco–Richmond 
• The Emerald Lounge’s Sippin’ Santa–Richmond 
• Hotel Greene’s Winterfreuden–Richmond 
• Noel at Beaucoup–Richmond 
• The Shack’ on 8th Winter Wonderland–Virginia Beach
• Miracle at Stellina–Roanoke 
• Sippin Santa at Tiki Thai–Reston
• Miracle on Exchange Street–Reston 
• Del Ray’s Joy on the Avenue Pop Up Bar–Alexandria
• Miracle on Waterside Drive–Norfolk

Another way to support Virginia’s drink scene? Head to Virginia’s distilleries, ABC stores, and vineyards to purchase a few locally-made spirits or wines as gifts for the imbibers in your life. 

If you prefer brews over cocktail bars, spirits, and wines, you’ll find seasonal ales available at practically every brewery in the Commonwealth, from spiced beers to gingerbread-inspired craft brews. 
 

see more: Seasonal Drinks & Holiday Pop-Ups 
 

2. Plan a Holiday Hotel Getaway

Escape the hustle and bustle of everyday living with a holiday getaway to an over-the-top decorated hotel in Virginia. Whether you're looking for a luxurious mountain retreat or a quaint countryside inn, Virginia offers festive accommodations that go all out with seasonal decorations, twinkling lights, and heartwarming amenities.

In addition to the season’s best accommodations, many hotels feature holiday-themed events, such as gingerbread house decorating, cozy afternoon teas, or visits from Santa Claus himself, making it the perfect opportunity to create lasting memories with loved ones. From romantic weekends for two to family-friendly staycations, a holiday hotel getaway in Virginia promises a magical and stress-free experience full of seasonal charm.

Save This Season: Even if you don't stay at a hotel, they can be great spots for taking festive photos. Many also host events that are open to the public. 
 

see more: 15+ Festive Hotels in Virginia
 

3. Visit a Decked-Out Virginia Town

Experience the magic of the season when you head to one of Virginia’s charming towns, all decked out in holiday splendor. These towns transform into awe-inspiring wonderlands that capture the heart of the holidays, with twinkling lights along Main Streets, tacky lights tours in festive neighborhoods, and extravagant window displays at boutique shops and restaurants. 

Stroll through historic districts adorned with wreaths, ribbons, and garlands, warm up with homemade hot cocoa at a local cafe, and attend seasonal events such as Christmas parades, tree lightings, and holiday markets. Plus, you can spend as much or as little as you like while seeing the holiday sights. Virginia’s Hallmark-worthy towns are sure to fill your heart with joy and nostalgia.
 

SEE MORE: Our favorite festive towns
 

4. Attend a Unique Virginia Holiday Celebration

This holiday season, immerse yourself in Virginia's festive charm by attending one of its unique holiday celebrations, where tradition and seasonal magic come to life in unforgettable ways. 

In the picturesque town of Middleburg, the Christmas in Middleburg Parade offers a delightful experience for visitors of all ages with a procession of horseback riders and hunting hounds celebrating the holiday season in the heart of Hunt Country. The free event takes place December 6. 

The beautiful mountains of Southwest Virginia are illuminated by thousands of lights at the Magical Christmas Village & Marketplace at Mountain Lake Lodge, open November 22 until January 3, 2026. This holiday celebration includes shopping in the Village, horse-drawn carriage rides, a life-size gingerbread house, glow-in-the-dark ice skating, live entertainment, and the Pinecone Express, a festive train providing rides around the mountaintop property. 

Head to some of Virginia’s historic colonial attractions like Jamestown or Colonial Williamsburg, where the Grand Illumination lights up the night with stunning displays of candles, twinkling lights, and even fireworks. These iconic sites also host special holiday events, from traditional caroling and colonial-era festivities to hands-on crafts for the entire family, creating an atmosphere that transports you to a simpler time while celebrating the joy of the season. 

Regent University’s CBN & Regent Christmas Village is a festive and family-friendly event running December 4–6 and 11–13, 2025. Get into the holiday spirit with sparkling lights, a towering 40-foot Christmas tree, horse-drawn carriage rides, a vibrant market, and a visit to Santa’s Cottage. It’s a magical celebration designed to create unforgettable holiday memories for all ages.

Whether you're taking in a small-town holiday parade, exploring quaint streets, enjoying historic reenactments, or simply marveling at the breathtaking holiday lights, Virginia’s seasonal celebrations offer a truly magical way to celebrate the holidays.
 

SEE MORE: Dozens of Holiday Events in Virginia 
 

5. Find Holiday Gifts in a Bustling Shopping District

This holiday season, make your gift-giving even more special by shopping for unique treasures in Virginia’s vibrant shopping districts. From local boutiques in historic downtowns to bustling open-air malls, Virginia offers a wealth of opportunities to find one-of-a-kind gifts for everyone on your list. 

Wander through the cobblestone streets of Alexandria's Old Town, where artisanal shops and cozy cafés set the perfect backdrop for a festive shopping spree. 

In Richmond's Carytown or Charlottesville's Downtown Mall, you'll discover a mix of locally crafted goods, vintage finds, and stylish fashion pieces—perfect for adding that personal touch to your holiday presents. 

Many districts are also beautifully adorned with holiday lights, live entertainment, and seasonal events, creating an inviting atmosphere that makes shopping feel like part of the celebration. Whether you're seeking handmade jewelry, specialty foods, or unique décor, Virginia’s shopping districts offer a festive experience filled with local charm and seasonal spirit.

If you’re unable to visit in person, consider supporting Virginia artisans and makers by shopping our Made in Virginia Gift Guide.
 

SEE MORE: 14 Shopping Destinations Worth the Trip
 

6. Pick out the Perfect Tree at a Local Farm

Kick off your holiday season with a visit to one of Virginia’s picturesque tree farms, where you can pick out the perfect Christmas tree to bring the spirit of the season into your home. Stroll through acres of fragrant evergreens, from classic Douglas Firs to fresh-cut Virginia pines, and choose the tree that best suits your holiday traditions. 

Most Virginia tree farms also offer hands-on family fun like hayrides, hot cocoa stands, and even visits from Santa Claus. A few farms even let you cut your own tree, giving you the chance to make lasting memories as you search for the perfect one. After choosing this year’s tree, relax by the fire pit or shop the farm’s additional seasonal offerings, from wreaths and garlands to local treats and gifts. 
 

see more: our favorite tree farms
 

7. See Dazzling Lights at a Virginia Theme Park

The magic of the season comes alive at Busch Gardens Williamsburg. The theme park goes all out for the holidays, stringing up millions of twinkling lights, festive decorations, and spectacular light shows set to classic holiday music. 

At Busch Gardens' Christmas Town, stroll through enchanted pathways lined with lights, sip on seasonal treats like hot chocolate, and enjoy festive performances that will get you in the holiday spirit.

8. Get Active on the Slopes at a Family-Friendly Mountain Resort

Get active on the slopes at one of Virginia's family-friendly winter resorts, where seasonal fun awaits at every turn. Wintergreen Resort, Massanutten Resort, the Omni Homestead Resort, and Bryce Resort offer a perfect mix of skiing, snowboarding, and tubing for all skill levels, making them ideal for families looking to enjoy outdoor adventures together. 

From seasoned skiers to first-timers, these Virginia resorts provide lessons and rentals, ensuring everyone can join in the fun. Off the slopes, you'll find cozy mountain accommodations and delicious dining options to warm up after a day on the slopes. With scenic mountain views, snow-covered trails, and a host of winter activities, Virginia’s mountain resorts offer outdoor adventure and holiday cheer for the whole family.
 

More to explore: Virginia's Mountain Resorts
 

9. Cozy Up with a Glass of Wine at a Virginia Vineyard

Escape into the tranquil beauty of Virginia’s wine country this holiday season and cozy up with a glass of locally crafted wine at one of the state’s many picturesque vineyards. 

Nestled in the foothills of the Blue Ridge Mountains or the rolling hills of the Shenandoah Valley, Virginia’s wineries offer a perfect retreat to enjoy the season’s best flavors. During this magical time of year, vineyards transform into festive havens for the holidays, with tasting rooms adorned in holiday decor and warmed by cozy fireplaces. Whether you're enjoying a quiet afternoon with friends or indulging in a wine-and-cheese pairing, a visit to a Virginia vineyard is the perfect way to savor the season and toast to the holidays in style.
 

SEE MORE: The coziest wineries for the winter
 

10. Take Family Photos in Front of a Decorated LOVEwork

Capture the spirit of the season with a memorable family photo in front of one of Virginia’s 300+ iconic LOVEworks. Scattered throughout the state, many of these creative LOVE sculptures are transformed for the holidays with festive wreaths, twinkling lights, and seasonal touches, making them the perfect backdrop for your family’s holiday photo.

Visiting a Virginia LOVEwork is a fun and free way to take home a snapshot of the holidays. As you gather together for these special photos, you’ll not only preserve memories for years to come but also take part in one of the state’s beloved traditions, spreading holiday cheer in true Virginia style.