Skip to content

Virginia

Shenandoah Apple and Wine Trail

Easy~44 mi point-to-point5 stops
Loading map…

About this farm route

Winchester calls itself the apple capital of Virginia and has the history to back it: the Shenandoah Apple Blossom Festival has run there since 1924, and Frederick and Clarke counties are still full of commercial orchards. This route strings four of them together and then climbs the eastern wall of the valley to finish in Bluemont, where the farms turn into vineyards. That transition is what makes the drive worth doing as one trip rather than two. You spend the first half in flat, open orchard country and the second half climbing switchbacks onto the Blue Ridge, and the vineyards at the top look back west over everything you just drove through.

Winchester apple country east over the Blue Ridge into the Loudoun vineyards at Bluemont.

Highlights

What earns the trip

  • Four working orchards in the heart of Virginia apple country
  • Finishes on the Blue Ridge with the valley view behind you
  • Orchards and vineyards on one route rather than picking between them
  • Under ninety minutes from the Washington DC suburbs

Stops

  1. 1

    Marker-Miller Orchards

    Winchester. Farm market and pick-your-own on the west side of town.

  2. 2

    La Grange Family Farm

    Stephens City. Just south of Winchester off the Valley Pike.

  3. 3

    Mackintosh Fruit Farm

    Berryville. Clarke County orchard, the last stop before the ridge.

  4. 4

    Bluemont Vineyard

    Bluemont. Up on the Blue Ridge, looking back west over the valley.

  5. 5

    Great Country Farms

    Bluemont. Pick-your-own and farm activities next door to the vineyard.

When to go

Best time to go

Late August through October for apples. Bloom in late April and early May is the other reason to come, and the vineyards run year round.

Planner estimate for the mapped line: 2h 56m

Before you go

Know before you go

  • The climb to Bluemont is steep and winding. It is fine in any car, but not a road to hurry.
  • Loudoun vineyards get very busy on fall weekends and several require a reservation.
  • If you are tasting at the end, sort out who is driving before you leave Winchester.

More farm routes

Browse all routes

In your pocket

Take farm country with you.

Free, no account needed. Farm maps, season checklists, and the crop identifier in your pocket.

  • Every farm stand and u-pick in your pocket

  • Plan a multi-stop farm day and save it

  • Snap a photo. AI names the crop

  • GPS tracking that keeps recording down the county road

A planned route with its distance, stops and elevation profile in the Farm Country Hubs app

For operators

Run a farm business?
Get on the map for free.

Claim your free listing for a branded page and a spot in the Farm Country Hubs app, then add bookings and digital waivers whenever you’re ready. No setup cost.