Winchester, Virginia

Private charter · Winchester, VA

Private charter to & from Winchester

Fly private to Winchester for apple country, Patsy Cline’s hometown, Civil War history and the northern gateway to the Shenandoah Valley

  • WGO
  • MRB
  • FRR

Photo: APK · CC BY-SA 4.0

Price a private flight from Winchester

Trip type
1

Times are local to each departure airport.

Fly private in Winchester

Winchester, without the hub.

3
Airports
5
Passengers
54
Direct routes

Winchester calls itself the oldest city west of the Blue Ridge, and it is the commercial center of the northern Shenandoah Valley. George Washington began his career here as a young surveyor and militia officer, and the city changed hands dozens of times during the Civil War. Apple orchards have long defined the surrounding countryside, while healthcare, manufacturing, logistics along I-81 and Shenandoah University support the modern economy. Country music fans know it as the hometown of Patsy Cline.

Winchester is roughly 75 miles from Washington, but traffic on I-66 and Route 7 can make the drive slow, and the region sits well beyond the airline airports. Winchester Regional Airport is just southeast of downtown, so a private flight makes visits to family, factories or orchards an easy day trip. Visitors come for the Old Town pedestrian mall, the Museum of the Shenandoah Valley, Civil War sites at Cedar Creek and Belle Grove, wineries and orchards, and the northern entrance to Skyline Drive at Front Royal.

Airports

Charter to and from Winchester airports

Fly into whichever airport puts you closest to where you're going. Littlebird flies to and from these airports in and around Winchester, and the price is for the whole airplane, however many seats you fill.

  • WGO

    Regional airport

    Winchester Regional Airport

    Winchester · KOKV

    From downtown
    3 mi
    Longest runway
    5,498 ft
  • MRB

    Commercial airport

    Eastern WV Regional Airport/Shepherd Field

    Martinsburg · KMRB

    From downtown
    18 mi
    Longest runway
    8,815 ft
  • FRR

    Regional airport

    Front Royal Warren County Airport

    Front Royal · KFRR

    From downtown
    19 mi
    Longest runway
    3,008 ft

Top attractions

Things to do in Winchester

When to go. Spring is Winchester’s showcase, as orchards bloom and the Shenandoah Apple Blossom Festival brings parades and events to the city in late April and early May. Fall is apple harvest season, with orchard visits and brilliant foliage in the Blue Ridge. Summers are warm and humid, and winters are cold with occasional snow. Festival weekends fill hotels quickly, so plan ahead.

  1. 01

    Old Town Winchester

    The brick-paved Loudoun Street Mall is the heart of the historic downtown, with restaurants, shops and the old Frederick County Courthouse, now a Civil War museum.

  2. 02

    Museum of the Shenandoah Valley

    This museum combines regional art and history galleries with the historic Glen Burnie house and six acres of formal gardens.

  3. 03

    Patsy Cline Historic House

    The modest home where Patsy Cline lived as a young woman is now a museum, with tours sharing her early life and rise to fame.

  4. 04

    Cedar Creek and Belle Grove National Historical Park

    South of Winchester, this park protects the site of a major 1864 battle and the eighteenth-century Belle Grove manor house.

  5. 05

    Skyline Drive

    The northern entrance of Shenandoah National Park at Front Royal opens the famous scenic road along the crest of the Blue Ridge, with overlooks and trails.

  6. 06

    Orchards and Wineries

    Frederick County’s orchards offer seasonal pick-your-own fruit and cider, and wineries in the surrounding countryside have tasting rooms with mountain views.

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