Pumpkin patches and fall festivals near Winchester: Marker-Miller's Pumpkin Festival Oct. 24, Shawnee Springs picking, Hill High Farm, corn mazes and hayrides.

Last checked Oct. 18, 2026. Updated each year. Dates come from the Winchester-Frederick County Convention and Visitors Bureau calendar and the farms’ own listings. Farm hours change with the weather; check before you drive out.

Fall around Winchester is orchard season. Most pumpkin patches and fall festivals are on farms in Frederick County, a short drive from the city line. The last full weekend of the season is Oct. 24-25, 2026.

Good to know

  • Full calendar: visitwinchesterva.com, or the Visitors Center at 1400 S. Pleasant Valley Road, 540-542-1326
  • Farm phone numbers below are as each farm lists them with the visitors bureau.
  • Halloween events are in our trick-or-treat guide.

Coming up

Date Event Where Cost
Friday, Oct. 23, 7 to 10 p.m. Flashlight Corn Maze and Moonlit Hayride (last night of the season) Russell Ridge Farm Market, 500 block of Hopewell Road, Clear Brook $8; free for 2 and under
Saturday, Oct. 24, 9 a.m. to 5 p.m. Pumpkin Festival Marker-Miller Orchards, 3035 Cedar Creek Grade See festival page
Saturday, Oct. 24, 10 a.m. to 4 p.m. Pumpkin Picking and Fall Fun (last Saturday) Shawnee Springs Market, 1488 Senseny Road Adults $5; under 18 free
Sunday, Oct. 25, 10 a.m. to 6 p.m. Tract-or-Treat Russell Ridge Farm Market, Clear Brook $10 ages 3 and up
Oct. 22-25 and 29-31 Haunted Nightmares Hill High Farm, 933 Barley Lane Tickets

Marker-Miller’s Pumpkin Festival has pumpkins already picked or pick-your-own, pumpkin pie, rolls, bars and doughnuts from the bakery, food from Blue Ridge Bar-B-Q, 3 Fires Oven Pizza and Stir Krazy Kettle Korn, crafters, a cow train for children and wagon rides. Festival page.

Shawnee Springs offers carving and specialty pumpkins, hayrides, an apple slingshot, a bounce house, pumpkin bowling and a touch-a-tractor.

Pumpkin patches and farm markets

From the visitors bureau’s farms list:

  • Marker-Miller Orchards and Farm Market, 3035 Cedar Creek Grade, 540-662-1391: pick-your-own produce, wagon rides, a playground, picnic areas and a bakery.
  • Hill High Farm, 933 Barley Lane, 540-667-7377: a seasonal pumpkin patch, hayrides, a corn maze and a haunted house. thepumpkin-patch.net.
  • Cline’s Farm, 920 Hopewell Road, 540-662-5684: seasonal produce and pick-your-own pumpkins.
  • Russell Ridge Farm Market, 500 block of Hopewell Road, Clear Brook: a corn maze, hayrides, a playground and pedal tractors.
  • West Oaks Farm Market, 4305 Middle Road: weekend fall fun with hayrides, corn mazes, live music and food trucks; free to enter, pay as you go.

Earlier this fall

The 2026 season opened with Marker-Miller’s first Honeycrisp Festival on Sept. 5, West Oaks’ Apple Harvest Festival on Oct. 3 and Marker-Miller’s Apple Harvest Festival on Oct. 10-11.

What this means for you

  • Oct. 24-25 brings Marker-Miller’s Pumpkin Festival and the last Shawnee Springs picking day.
  • Check each farm’s page for weather closures before you go.
  • More events: things to do this month and farmers markets.

Frequently asked questions

Where can I pick pumpkins near Winchester, Virginia?

Marker-Miller Orchards, 3035 Cedar Creek Grade, has pick-your-own pumpkins at its Pumpkin Festival on Saturday, Oct. 24. Shawnee Springs Market, Cline’s Farm and Hill High Farm also offer pumpkins in season.

Is there a corn maze near Winchester?

Yes. Russell Ridge Farm Market in Clear Brook has a corn maze, with its last flashlight maze and moonlit hayride night on Friday, Oct. 23, from 7 to 10 p.m. Hill High Farm, 933 Barley Lane, also lists a corn maze.

How much is Shawnee Springs pumpkin picking?

Admission is $5 for adults and free for anyone under 18 on its pumpkin picking Saturdays, which end Oct. 24, 2026.