10 Weekend Trips That Feel Like a Month-Long Journey

2. Shenandoah & Skyline Drive, Virginia — Slow driving, hilltop overlooks, and small-town stops

Skyline Drive through Shenandoah is an intentionally slow road trip where overlooks create natural pause points. Pull over for short ridge hikes, wander into small towns like Luray or Sperryville for local markets, and book a cozy bed-and-breakfast that encourages lingering breakfasts and porch time. The route is compact enough to avoid long daily transfers while giving a steady stream of changing views that mimic the variety of a longer tour. Logistics: from Washington, D.C. it’s a 1.5–2 hour drive to the park entrances; Charlottesville is within an hour. Budgets (per person, As of November 2025): budget $80–$180; mid-range $180–$350; splurge $350+. Best season: fall for foliage, spring for wildflowers. Accessibility & family note: several overlooks and short trails are family-friendly; some hikes include moderate elevation. Quick itinerary: Friday evening — check into a B&B near Skyline Drive; Saturday — morning overlook hikes, lunch in a small town, afternoon scenic drive; Sunday — short nature walk then head home.