2-Hour Road Trips from Arlington to Take This Holiday Season

Updated: November 2025
The best 2-hour road trips from Arlington, VA for the holiday season include Middleburg, Charlottesville, Leesburg, Old Town Alexandria, and Fredericksburg. Each destination offers festive markets, holiday lights, cozy inns, and small-town charm — all within easy driving distance of the DMV.

When the holidays hit, there’s nothing better than packing the car, grabbing a coffee, and hitting the road for a cozy winter escape. Luckily, you don’t have to go far to find twinkling lights, festive small towns, and hot chocolate worth the drive.

Here are five of our favorite 2-hour (or less) road trips from Arlington, VA to make your holiday season a little more magical.

TLDR: Quick Snapshot

🎄 Perfect for: Families, couples, or friends who love holiday markets, small towns, and scenic drives.
🚗 Drive time: 2 hours or less from Arlington.
🕯️ Vibe: Cozy, festive, and full of photo-worthy moments.
🌟 Top picks: Middleburg, Charlottesville, Leesburg, Old Town Alexandria, and Fredericksburg.

1. Middleburg, VA – Horse Country Holiday Magic (1 hr)

Middleburg might be the most picturesque holiday town in Northern Virginia. The annual Christmas in Middleburg Parade brings horses, hounds, and carriages down Washington Street, and the entire town transforms into a postcard scene. Shop local boutiques, sip hot cider at Red Fox Inn, and admire the wreaths adorning every door.

Don’t Miss: Christmas in Middleburg (early December), tasting rooms along Route 50, and Salamander Resort’s winter spa specials.

2. Charlottesville, VA – Wine, Lights, and Cozy Inns (2 hrs)

Charlottesville shines in December. Explore the Downtown Mall’s holiday market, tour nearby wineries decked out for the season, and stroll through Monticello’s Holiday Open House for a touch of history. End your night at a local inn with a glass of Virginia red by the fire.

Don’t Miss: Pippin Hill Vineyards, Monticello holiday tours, and lights at Boar’s Head Resort.

3. Leesburg, VA – Shopping & Small-Town Cheer (45 min)

Leesburg mixes charm with convenience. Explore the Village at Leesburg’s holiday ice rink, stop by historic downtown for boutique shopping, and enjoy festive light displays throughout Loudoun County. It’s an easy day trip with plenty of restaurants and kid-friendly fun.

Don’t Miss: Leesburg Premium Outlets for gifts, Delirium Café for a warm drink, and Lights on the Green.

4. Old Town Alexandria, VA – Waterfront Winter Wonderland (15 min)

You don’t even have to leave Arlington’s backyard for this one. Old Town Alexandria is a holiday dream — cobblestone streets, candlelight tours, and the iconic Scottish Christmas Walk Parade. Sip cocoa, browse local shops, and watch the Holiday Boat Parade of Lights on the Potomac.

Don’t Miss: The Torpedo Factory’s Holiday Art Market and festive photos along King Street.

5. Fredericksburg, VA – Colonial Charm & Candlelight (1 hr 15 min)

Historic Fredericksburg is full of old-town character, antique shops, and twinkling lights. Take a candlelight walking tour, explore local bakeries, and stroll Caroline Street for vintage finds. It’s a perfect mix of history, coziness, and classic Virginia charm.

Don’t Miss: LibertyTown Arts Workshop and the Fredericksburg Holiday Craft Show.

Key Takeaways

• You don’t need to travel far for a festive getaway — every destination here is under two hours.

• Middleburg and Old Town Alexandria offer the most iconic holiday experiences.

• Charlottesville and Fredericksburg mix charm with rich history.

• Leesburg is perfect for quick day trips and family-friendly outings.

• All destinations make great weekend escapes or last-minute gift-shopping adventures.

FAQs

Q: What’s the best time to visit these towns for holiday events?
A: Most holiday markets and parades happen from Thanksgiving weekend through mid-December.

Q: Are these trips family-friendly?
A: Yes — each destination offers plenty of family activities, from parades to ice skating.

Q: Are pets allowed at most spots?
A: Many towns, including Middleburg and Alexandria, are pet-friendly (just check event details first).

Q: What’s the best route to avoid traffic leaving Arlington?
A: Leave early or after rush hour, especially on Fridays. Use GW Parkway or Route 50 for scenic alternatives.

Q: Which destination is best for couples?
A: Charlottesville — cozy inns, wineries, and festive dinners make it ideal for a romantic weekend.

🎄 Want to see more holiday fun around Arlington?
Head to our Instagram for local holiday guides, events, and restaurant picks around town!

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