5 Fall Getaways Within 2 Hours of Arlington, VA

Looking for a quick fall escape that will not eat your whole weekend? These five destinations deliver foliage views, small town strolls, and great food within about two hours of Arlington. Pack a light jacket, cue up a road playlist, and go.
Updated: October 2025 · Arlington, VA

TLDR

• Skyline Drive for overlooks and short hikes.

• Harpers Ferry for rivers, trails, and a historic village.

• Annapolis for waterfront eats and cobblestone charm.

• Loudoun Wine Country for tastings around Middleburg and Leesburg.

• Gettysburg for history, rolling farms, and quiet sunset drives.

1) Shenandoah National Park and Skyline Drive

Vibe: Mountain overlooks, short hikes, waterfalls, and classic foliage views.
Drive time from Arlington: about 1.5 to 2 hours to the North District.
Do this: Pick two or three overlooks, add a short loop like Fox Hollow or a waterfall walk, and plan a picnic.
Eat and sip: Grab provisions before you go or stop at a wayside for a simple lunch.
Pro tip: Arrive early for easier parking at trailheads and bring layers for windy overlooks.

2) Harpers Ferry, West Virginia

Vibe: A postcard river town where the Shenandoah meets the Potomac.
Drive time from Arlington: about 1 to 1.5 hours.
Do this: Walk the lower town, cross the footbridge for towpath views, or climb Maryland Heights for a panorama.
Eat and sip: Cozy cafes and taprooms line the main streets.
Pro tip: Wear sturdy shoes for mixed surfaces and check train times if you are arriving by rail.

3) Annapolis, Maryland

Vibe: Nautical streets, brick sidewalks, and waterfront restaurants.
Drive time from Arlington: about 1 to 1.5 hours.
Do this: Stroll City Dock, tour the historic core, and book a short harbor cruise if weather cooperates.
Eat and sip: Crab cakes, oysters, and warm drinks on patio heaters when the breeze picks up.
Pro tip: Park once and explore on foot to make the day easy.

4) Loudoun Wine Country: Middleburg and Leesburg

Vibe: Horse country roads, vineyard views, and relaxed tastings.
Drive time from Arlington: about 45 to 75 minutes depending on your route.
Do this: Build a two stop tasting plan, add a farm market or creamery, and finish with a sunset photo at a hilltop winery.
Eat and sip: Pack a picnic or choose a tasting room with a kitchen.
Pro tip: Book tastings in advance on peak October weekends and designate a driver.

5) Gettysburg, Pennsylvania

Vibe: Wide open fields, history, and calm autumn drives.
Drive time from Arlington: about 2 hours.
Do this: Drive the auto tour, walk a sunset loop near the high ground, and visit town for dinner.
Eat and sip: Casual taverns and local bakeries make for an easy end to the day.
Pro tip: Bring binoculars. The fields and tree lines glow at golden hour.

Sample one day itinerary

• Morning: Drive to Skyline Drive. Two overlooks and one short hike.

• Midday: Picnic at an overlook.

• Afternoon: Roll back east for a vineyard stop in Loudoun.

• Evening: Dinner in Middleburg or Leesburg and home by bedtime.

Packing list

• Light jacket and hat

• Water bottle and trail snacks

• Portable phone charger

• Small blanket for picnics

• Comfortable shoes you can walk in all day

Key Takeaways

• Five strong fall destinations sit within two hours of Arlington.

• Mix mountains, rivers, waterfronts, and vineyards in one weekend.

• Book tastings and arrive early at popular parks on October weekends.

FAQ

Which spot is best with kids?
Harpers Ferry for exploring and easy paths, or Annapolis for walkable streets and boat watching.

Where will I get the best foliage?
Skyline Drive is the safe bet. Loudoun country roads offer beautiful color too.

Do I need reservations?
Wine tastings and popular dinner spots often require them in October. Parks are first come, first served for parking.

Can I do two places in one day?
Yes. Try Skyline Drive in the morning and a Loudoun tasting at sunset, or Annapolis for lunch and a quick stop in Old Town on the way back.

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Fine print: This article is for informational purposes only and is not legal, financial, tax, medical, or professional advice. Information is provided in good faith from sources believed to be reliable, but accuracy and completeness are not guaranteed. Dates, times, prices, availability, and policies can change without notice. Verify details directly with the venue, organizer, County, or applicable authority before making decisions. Discover Arlington, The Davenport Group, and TTR Sotheby’s International Realty are not responsible for errors or omissions or for any loss arising from reliance on this content. Equal Housing Opportunity. Events notice: Event details and participation requirements can change. Always confirm directly with the organizer. Participation is at your own risk and you agree to follow posted rules and local guidance.

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