12 Days Of Cheer In Leesburg: Making This A December To Remember

The holiday season is officially here, and there’s no shortage of ways to soak up the magic in and around Leesburg. To help get you in the spirit, we’ve rounded up a dozen festive ideas you can enjoy throughout the month — each one a fun, joyful way to celebrate the season close to home.

From twinkling light displays and holiday markets to cozy treats, local shopping spots, winter activities and seasonal shows, these 12 picks highlight what makes Leesburg feel especially merry this time of year. Whether you check off one or all twelve, it’s all about slowing down, supporting local businesses and making memories.

1. Walk through a glowing winter wonderland at Winter City Lights.

If you're looking for an immersive holiday light experience near Leesburg, Winter City Lights transforms 18 acres into one of the most advanced walk-through displays in the country. The 1.5-mile trail winds through massive ornaments, light tunnels, synchronized shows, and a 52-foot “dancing” Christmas tree, all set to nightly snowfall. You can stay longer for snow tubing, cozy bonfires and treats like s’mores and funnel cakes. Tickets must be reserved online, with select dates running Nov. 28 through Dec. 29, available here.

2. Lace up for holiday public skating at ION: The Rinks at Compass Creek.

Spend a festive afternoon gliding across the ice at ION International Training Center, which offers public skating sessions every weekend in December. It’s a popular spot, especially during the holidays, so arriving 15–20 minutes early helps with check-in and skate rentals. Keep an eye on their schedule, updated weekly, and consider stopping by for special events like the Dec. 5 Holiday Tree Lighting or Skate with the Grinch & Santa on Dec. 20.

3. Sip a cozy seasonal latte at Second Nature Coffee Co.

Set inside a historic Leesburg home, Second Nature Coffee Co. is the perfect warm-up spot for a December morning or a break between holiday errands. The shop is loved for its welcoming atmosphere, seasonal drinks and fresh baked goods — plus outdoor seating when the weather cooperates. It's the kind of place where the baristas remember your name and the vibe feels like a holiday hug. Stop in before browsing the shops in downtown Leesburg or after an evening of light viewing around town.

4. Shop local gifts and Virginia-made treats at Very Virginia.

For uniquely local holiday gifts, Very Virginia is a downtown staple packed with artisan items, gourmet snacks, regional souvenirs and charming Virginia-themed goods. The shop is known for its warm Southern hospitality, making browsing feel like part of the holiday experience. From local honey and peanuts to handmade candles and horse-country keepsakes, it’s an easy place to finish your gift list. They also offer curated gift baskets perfect for hosts, coworkers or out-of-town family.

5. Enjoy craft beer and live music at Vanish Farmwoods Brewery.

Just outside Leesburg, Vanish Farmwoods Brewery sits on 63 scenic acres with a relaxed, festive atmosphere that’s perfect for winter gatherings. With up to 20 beers on tap, fire pits and wide-open mountain views, it’s a great spot to unwind after a day of holiday shopping. December often brings live music — check the event lineup to plan your visit around a show. Bring friends, grab a table indoors or outdoors and soak up the farm-brewery atmosphere.

6. Tune your radio to 98.3 and enjoy the Woodlea Hills Lights show.

The annual Woodlea Hills Lights display transforms a local neighborhood home into a synchronized musical light show, drawing families from all over Leesburg. With nearly 30,000 LEDs, pixel effects, singing bulbs, arches and a towering mega tree, the show grows more impressive every year. Simply pull up, tune your car radio to 98.3 FM and watch the lights dance in time with the music. You can preview past shows on their YouTube channel to get a taste of the magic.

7. Bowl, brunch or join a holiday event at The Branch.

Retro-meets-modern at The Branch, Leesburg’s revamped bowling alley, offering great food, a full bar and plenty of December happenings. It's a fun pick for family outings, date nights or group gatherings, especially with weekend brunch and late-night half-price bowling on Saturdays. Their holiday events calendar is packed, including Christmas-themed Music Bingo (Dec. 4), Breakfast with Santa (Dec. 14) and an Ugly Christmas Sweater Contest (Dec. 19). Check the full list here before planning your visit.

8. Find a new read — and maybe a new plant — at Birch Tree Bookstore.

A cozy, woman-owned indie bookstore in historic downtown, Birch Tree Bookstore offers a curated selection of books plus a unique twist: it shares space with Foliage Plants. It's a warm, welcoming spot to pick up holiday gifts, browse staff recommendations or unwind with a new winter read. December often includes workshops, storytimes and small holiday markets: see upcoming events here. Open daily, it’s an easy stop during a stroll through downtown Leesburg.

9. Browse holiday deals and designer finds at Leesburg Premium Outlets.

With over 100 designer and name-brand stores, Leesburg Premium Outlets is a go-to spot for holiday shopping and December savings. The outdoor center features fire-pit seating, updated lounges and play areas, making it a comfortable place to spend an afternoon. From Michael Kors to Under Armour to Burberry, you can tackle your entire gift list in one visit. Located near Loudoun’s wine country and airport corridor, it’s also an easy stop for visiting friends and family.

10. Catch a holiday concert or show at Tally Ho Theater.

A restored Depression-era movie palace, Tally Ho Theater hosts a full December lineup with everything from rock tributes to seasonal performances like the 16th Annual Jingle Jam. The venue blends Art Deco charm with modern sound, making it a memorable place to enjoy live music during the holiday season. You can order food from the restaurant next door and grab drinks from one of the three indoor bars.

11. Learn to ski indoors at Inside Ski Training Center.

Whether you're prepping for a winter trip or trying skiing for the first time, Inside Ski offers an innovative indoor slope experience right in Leesburg. Their revolving “endless” ski deck simulates a real mountain run with adjustable pitch and speed, giving beginners and seasoned skiers a chance to practice safely. Certified instructors guide lessons for kids and adults and pricing starts at $89 for group sessions. It’s a fun, active way to embrace winter — no snow required.

12. Sip wine and take in mountain views at Stone Tower Winery.

Spend a December afternoon unwinding at Stone Tower Winery, a picturesque estate on Hogback Mountain offering tastings, tours and stunning views. With two tasting rooms (one family-friendly, one club-exclusive), it’s easy to settle in with a glass and enjoy the holiday atmosphere. Their educational tours and specialty experiences make great seasonal outings, especially for visiting friends or relatives. Walk-ins are welcome for groups of eight or fewer and larger groups can reserve pergolas or private spaces for a festive gathering.

Stay warm, shop local and enjoy every twinkling moment — happy holidays, Leesburg!

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