October in Winchester: pumpkin festivals Oct. 24, ghost tours on the mall Oct. 28-31, Haunted Nightmares, the Big Cheese Festival and the Last Sunday Market.

Last checked Oct. 18, 2026. Rebuilt on the first of each month. Listings come from the Winchester-Frederick County Convention and Visitors Bureau calendar, Friends of Old Town and the City of Winchester. Confirm with the organizer before you go.

The rest of October in Winchester is pumpkins, apples and ghosts: orchard festivals on the edge of the city, a haunted house, nightly ghost tours on the walking mall over Halloween week and a busy weekend of food and wine on Oct. 24-25. For Halloween night itself, see our trick-or-treat guide; for more farm days, our fall festivals and pumpkin patches guide.

Good to know

  • Visitor information: Winchester-Frederick County Visitors Center, 1400 S. Pleasant Valley Road. The bureau’s calendar has the full list.
  • Parks and city events: Winchester Parks and Recreation, 540-662-4946
  • Several events are in Frederick County, just outside the city line; the town is given for each.

This week: Oct. 18-24

  • Sunday with a Sentry, Sunday, Oct. 18, noon to 2 p.m. George Washington’s Fort Loudoun Historic Site, 419 N. Loudoun St., opens rain or shine with site tours, the restored well and an archaeological trench. It is the last of the 2026 Sunday openings. Details.
  • Godfrey Miller Center art show, Wednesday, Oct. 21, 5 to 6 p.m. Opening reception for the center’s annual show, 28 S. Loudoun St. Details.
  • Thursday on the Farm, Thursdays, 6 to 9 p.m. Bluegrass at the Homestead Farm at Fruit Hill Orchard, 2502 N. Frederick Pike: dinner from 6 to 7 p.m., music from 7 to 9 p.m. Bring a lawn chair. Details.
  • Flashlight Corn Maze and Moonlit Hayride, Friday, Oct. 23, 7 to 10 p.m. Russell Ridge Farm Market, 500 block of Hopewell Road, Clear Brook. $8; free for 2 and under. The last night of the season.

Saturday, Oct. 24

  • Pumpkin Festival, 9 a.m. to 5 p.m. Marker-Miller Orchards, 3035 Cedar Creek Grade: pick-your-own pumpkins, a bakery, food trucks, crafters, a cow train and wagon rides. Details.
  • Pumpkin Picking and Fall Fun, 10 a.m. to 4 p.m. Shawnee Springs Market, 1488 Senseny Road: hayrides, an apple slingshot and a bounce house. Adults $5; under 18 free.
  • The Big Cheese Festival, noon to 6 p.m. James Charles Winery and Vineyard, 4063 Middle Road: wine and cheese pairings from three wineries, live music and food trucks; ticketed. Tickets.
  • Family History and Genealogy Celebration, 10 a.m. to 3 p.m. 399 Apple Pie Ridge Road: classes and exhibitors for family history researchers.
  • Halloween Happenings, 5 to 8 p.m. Clearbrook Park, 130 Poolside Drive, Clear Brook: a Howl-O-Ween dog parade, then trick-or-treat sessions through the park. Details in our trick-or-treat guide.
  • Handley Avenue block party, 3 to 7 p.m. Handley Avenue between Leicester and Clifford streets is closed for it.

Sunday, Oct. 25

  • The Last Sunday Market, 10 a.m. to 2 p.m. An indoor makers and growers market in the Exchange on Loudoun, 186 N. Loudoun St., on the walking mall: produce, baked goods, honey, eggs and handmade goods. It returns Nov. 29.
  • Tract-or-Treat, 10 a.m. to 6 p.m. Russell Ridge Farm Market, Clear Brook: trick-or-treat at tractors around the farm, plus the corn maze and hayrides. $10 for ages 3 and up.

Halloween week: Oct. 26-31

  • Haunted History Ghost Tour, 6 p.m. Oct. 28, 29, 30 and 31. About an hour through Old Town, from the south entrance of the Loudoun Street Mall, 141 S. Loudoun St. Buy tickets ahead through the visitors bureau.
  • Haunted Nightmares, Oct. 22-25 and Oct. 29-31. A haunted house and escape rooms at Hill High Farm, 933 Barley Lane. Saturday and Sunday from 1 to 5 p.m. it runs a less aggressive daylight show for younger visitors. Times and tickets.
  • ~Nois Quartet, 8 p.m. Thursday, Oct. 29. The Chicago saxophone quartet at the Bright Box Theater, 15 N. Loudoun St.
  • Fall Art Series, 10 to 11 a.m. Saturdays, Oct. 24 and 31. Free abstract art classes for children 6 to 12 at the Youth Development Center, 302 S. Loudoun St.

Looking ahead to November

  • Free community dance night, 7 to 9 p.m. Wednesday, Nov. 4, at Vibrissa Beer, 10 N. Kent St.
  • Veterans Day, Wednesday, Nov. 11: no city trash or recycling pickup that day; see the trash guide.
  • “The Wickhams: Christmas at Pemberley,” Nov. 13-28, at Winchester Little Theatre, 315 W. Boscawen St.
  • “Into the Woods,” Nov. 13-15, at the Patsy Cline Theatre at John Handley High School, a systemwide Winchester Public Schools production: 7 p.m. Friday, Nov. 13; 2 and 7 p.m. Saturday, Nov. 14; and 2 p.m. Sunday, Nov. 15. Show details from the school division, tickets on GoFan.
  • Festival of Trees, Saturday, Nov. 21, at the Youth Development Center, 302 S. Loudoun St.
  • Holiday Parade and tree lighting, 7 p.m. Monday, Nov. 30, downtown. See our Christmas parade guide.

More every week: things to do this weekend.

Winchester’s big yearly events, each on its own page: the Shenandoah Apple Blossom Festival (the 100th, April 23 to May 2, 2027), the Frederick County Fair, the Patsy Cline Block Party and the Rotary club’s Apple Harvest Festival.

Frequently asked questions

What is there to do in Winchester, Virginia, this weekend?

On Saturday, Oct. 24, Marker-Miller Orchards holds its Pumpkin Festival from 9 a.m. to 5 p.m., Shawnee Springs Market has pumpkin picking from 10 a.m. to 4 p.m. and James Charles Winery hosts the Big Cheese Festival from noon to 6 p.m. The Last Sunday Market is 10 a.m. to 2 p.m. Sunday, Oct. 25, on the walking mall.

Are there ghost tours in Winchester?

Yes. The Haunted History Ghost Tour leaves from the south entrance of the Loudoun Street Mall at 6 p.m. Oct. 28, 29, 30 and 31. It lasts about an hour and tickets must be bought ahead through the visitors bureau.

Where is the haunted house near Winchester?

Haunted Nightmares at Hill High Farm, 933 Barley Lane, runs Oct. 22-25 and Oct. 29-31. On Saturday and Sunday afternoons from 1 to 5 p.m. it runs a less intense daylight show for younger visitors.