Oakton, Virginia: 10 Best Short Road Trips Near Fairfax

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10 Fun Out-of-County Road Trips Near Oakton, Virginia

Living in or near Oakton, VA and itching to get out of town for a bit? The good news is you’re surrounded by some of the best day trip spots in the Mid-Atlantic. In less than an hour or so, you can be walking historic streets, hiking along rivers, or sipping wine with mountain views—all without hopping on a plane. This guide shares 10 easy out-of-county road trips from Oakton, focusing on nearby counties like Arlington, Loudoun, Prince William, Charles (MD), Montgomery (MD), Prince George’s (MD), and the independent cities of Alexandria, Fairfax, and Falls Church. Each idea is perfect for a quick escape, a family Saturday, or a laid-back date.

1. Old Town Alexandria – Cobblestone Streets & Waterfront Charm

If you want that “mini-vacation” feeling without going far, head to Old Town Alexandria in Alexandria City, VA, about 25–35 minutes from Oakton depending on traffic. Stroll along King Street, where colorful row houses, boutiques, and cafes line the sidewalk. The Alexandria waterfront is a great place to grab a bench, watch the boats, and just breathe for a minute.
  • Don’t miss: The Torpedo Factory Art Center – a former munitions factory turned art hub with working studios.
  • Best for: Couples, friends, or solo wanderers who like history and cute shops.
  • Road trip tip: Street parking can be tight. Consider one of the garages closer to the waterfront.
If you’ve been to Old Town before, try going in the late afternoon, then stay for dinner. The town feels totally different once the lights come on along the river.

2. Arlington’s Memorials & Views – A Different Look at D.C.

Right across the river from Washington, D.C., Arlington County, VA offers powerful history and some of the best skyline views of the nation’s capital. Start at Arlington National Cemetery. It’s sobering, quiet, and beautiful in a very simple way. Seeing the Tomb of the Unknown Soldier and the changing of the guard in person is something you don’t forget. Afterward, head over to the U.S. Marine Corps War Memorial (Iwo Jima Memorial). The view toward the National Mall, especially at sunset, is incredible.
  • Don’t miss: The John F. Kennedy gravesite and the eternal flame at the cemetery.
  • Best for: History lovers, families with teens, out-of-town guests.
  • Road trip tip: Wear comfortable shoes; you’ll walk more than you think.
If you’ve ever watched a D.C. fireworks show on TV, imagine actually being there on the hill by Iwo Jima—that’s the kind of view you get.

3. Leesburg & Loudoun Wine Country – Small Town + Big Views

Looking for a slower pace? Point your car toward Leesburg in Loudoun County, VA, roughly 40–50 minutes from Oakton. Downtown Leesburg has that classic small-town vibe: brick sidewalks, antique shops, and plenty of local restaurants. But the real star is the surrounding Loudoun wine country. Within a short drive of town, you’ll find rolling hills, scenic vineyards, and wineries with decks that make you want to sit for hours.
  • Don’t miss: A tasting at one of the many wineries or cideries just outside town.
  • Best for: Couples, friend groups, low-key birthdays, and “we just need a break” days.
  • Road trip tip: Designate a driver or use a local tour service if you’re visiting multiple wineries.
On my first drive out there, I remember thinking, “Wait, this is less than an hour from Northern Virginia traffic… really?” The open views make it feel like you’ve gone much farther.

4. Historic Occoquan – Riverfront Strolls in Prince William County

Just south of Fairfax County, right across the Occoquan River, sits the small but charming town of Occoquan in Prince William County, VA. It’s an easy 35–45 minute drive from Oakton and feels like a step back in time, with old mill buildings and cozy shops lined up along narrow streets.
  • Things to do:
    • Walk along the riverfront path.
    • Browse local art, gifts, and antiques.
    • Have lunch on a patio overlooking the water.
  • Best for: Half-day getaways, relaxed weekends, or showing off “small-town Virginia” to visitors.
  • Road trip tip: Occoquan hosts seasonal craft fairs that get busy, so arrive early on those weekends.
It’s the kind of place where you can park once, wander around without a plan, and still feel like you had a solid little adventure.

5. Fairfax City – Historic District & Local Eats

Even though Oakton is close to Fairfax, anything inside the City of Fairfax is technically outside Fairfax County itself, which makes it fair game for a quick out-of-county road trip. Downtown Fairfax City has grown into a fun mix of old and new. You’ll find historic buildings mixed with modern restaurants, coffee shops, and ice cream spots.
  • Don’t miss: Walking the compact historic district and checking out the local murals and markers.
  • Best for: Families with younger kids, students, and anyone wanting something close but not boring.
  • Road trip tip: Pair your visit with a local event or festival—Fairfax City has plenty throughout the year.
If you only have a few hours but still want to “go somewhere,” Fairfax City is a smart pick. It doesn’t feel as intense as D.C., but it still gives you that sense of being out and about.

6. Falls Church City – Tiny City, Big Flavor

Just east of Oakton sits the independent City of Falls Church, sometimes called “The Little City.” It’s small in size but big on personality. Here, the fun is all about food and local spots. You’ll find a broad mix of restaurants—from simple burger joints and diners to global eats—packed into a very walkable area.
  • Things to try:
    • Grab brunch or coffee, then walk around the city center.
    • Catch a local performance or community event when available.
  • Best for: Quick evening trips, casual date nights, or a “let’s try a new place for dinner” outing.
  • Road trip tip: Because it’s compact, parking can feel limited at peak times—plan a bit of extra time to find a spot.
If you’ve ever said, “We always go to the same restaurants,” Falls Church is an easy way to break the habit without a long drive.

7. National Harbor & MGM – Waterfront Fun in Prince George’s County, MD

Cross the Potomac River into Prince George’s County, Maryland and you’ll hit National Harbor, a colorful waterfront area that feels almost like a small resort town. From Oakton, it’s usually about a 40–55 minute drive, depending on traffic and your route.
  • Things to do:
    • Ride the Capital Wheel for sweeping views of the river.
    • Walk along the waterfront and browse shops.
    • Visit MGM National Harbor for dining, entertainment, and casino gaming (for adults).
  • Best for: Date nights, group hangouts, birthdays, or anyone who wants some nightlife without going downtown D.C.
  • Road trip tip: Evening visits feel extra festive with all the lights and activity.
If you like the idea of a boardwalk-style outing but don’t have time for the beach, National Harbor is a solid stand-in.

8. Bethesda & Cabin John – Food and Nature in Montgomery County, MD

Head north into Montgomery County, Maryland and spend a day split between city-style dining and quiet outdoor time. Start in Bethesda, about 40–50 minutes from Oakton, and explore its walkable downtown full of cafes, bakeries, and restaurants. Then, drive a short distance to places like Cabin John Regional Park for trails, playgrounds, and open space.
  • Don’t miss: Grabbing lunch or coffee in Bethesda, then walking it off under the trees in the park.
  • Best for: Families, couples, or anyone who likes to mix urban and outdoor time in one trip.
  • Road trip tip: If you’re traveling during rush hour, expect extra time crossing the river and approaching Bethesda.
This combo day trip is great if you like options: if the weather’s perfect, lean into the park; if it turns rainy, just stick to Bethesda’s indoor spots.

9. Southern Maryland Scenic Drive – Charles County Back Roads

If you’re craving more open roads and less traffic, point your car toward Charles County, Maryland. It’s a bit farther than some of the other trips, but the change of scenery is worth it. You’ll find a mix of farmland, small communities, and Potomac River views. Plan a route that takes you near the water or through some of the quieter back roads.
  • Things to do:
    • Take a slow drive and enjoy the wide-open spaces.
    • Stop in a small town for lunch at a local spot.
    • Look for river access points or parks to stretch your legs.
  • Best for: Sunday drives, couples who like exploring, and anyone who wants a real “out of the suburbs” feel.
  • Road trip tip: Fill up your gas tank before you leave and keep a loose plan—cell service can be spotty in some back-road areas.
If your weeks are packed with screens, deadlines, and constant noise, this kind of simple drive can be surprisingly refreshing.

10. Old Town Manassas – Railroad History & Small-Town Vibes

Another great Prince William County day trip is Old Town Manassas, about 40–50 minutes from Oakton, depending on your route. The historic downtown area centers on the train tracks and the old station, giving it a classic railroad town feel. It’s compact and walkable, with plenty of local shops, restaurants, and seasonal events.
  • Don’t miss: Strolling around the town square and checking out the old train depot and nearby historic markers.
  • Best for: Families, casual history fans, or anyone who enjoys relaxed small-town exploring.
  • Road trip tip: Check the local calendar—Manassas often hosts festivals, outdoor concerts, and parades that can make your visit even more fun.
It’s the kind of place where you can grab an ice cream, sit on a bench by the tracks, and watch the world go by for a while.

How to Make the Most of These Oakton Road Trips

To keep your out-of-county adventures from turning into stress-fests, a tiny bit of planning goes a long way:
  • Check traffic: Northern Virginia and the D.C. area can be unpredictable—leaving a little early can save a lot of time.
  • Pick a theme: Ask yourself, “Do we want history, food, nature, or nightlife today?” Then choose a spot that fits.
  • Keep it simple: You don’t need an hour-by-hour plan. One or two main stops per trip is usually enough.
Think of these places as your extended backyard. From Oakton, you can reach a surprising variety of experiences—waterfronts, wine country, small towns, and big views—often in under an hour.

Share Your Favorite Road Trips Near Oakton

Have you tried any of these out-of-county adventures from Oakton? Maybe you’ve found a favorite winery in Loudoun, a hidden cafe in Falls Church, or the perfect sunset spot in Arlington.
  • Which day trip on this list are you most excited to try?
  • Did I miss a hidden gem in one of these nearby counties?
Drop your tips and stories in the comments—your experience might help someone else plan their next weekend escape. And if you found this guide helpful, please share it with friends, neighbors, or family in Oakton and nearby areas. Sometimes, all someone needs is a little nudge (and a short drive) to discover something new just beyond their own county line.
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