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Haunted trails, free Halloween festivals, live music, local markets, and a few longer day trips worth considering.
If you haven't made plans for October 23–25, there's quite a bit going on around the Shenandoah Valley. Harrisonburg has its annual Skeleton Festival, Winchester is hosting a wine and cheese event, and South River Farm in Front Royal is opening its haunted trail and corn maze after dark. There are also several free family activities, a Sunday market, and a few options farther out if you don't mind the drive. Here's what's happening and what I'd check before heading out.
At a glance
| Event | When | Admission |
|---|---|---|
| Harvest of Horror, South River Farm, Front Royal | Fri and Sat, 7–10 p.m. | Price not listed |
| Skeleton Festival, Harrisonburg | Sat 1–5 p.m. Sensory-friendly trick-or-treating noon–1. Costume contest 3:30 p.m. on Court Square. | Free |
| The Big Cheese, James Charles Winery, Winchester | Sat noon–6 p.m. | $20 in advance or $25 at the door. Under 12 free. |
| Monster Mash, Charlottesville | Sat 2–4 p.m. | Free |
| Boo at the Moo, Dairy Market | Sat 3–6 p.m. | Free with RSVP |
| Farm to Market on Main, Front Royal | Sun 9 a.m.–1 p.m. | No admission listed |
The 5K and the bands are Saturday too, if a morning run or an all-day wristband sounds better than costumes.
The map
Brown pins are the plans close to home. Blue pins are the longer day trips, outside this first view. In Harrisonburg the Skeletons, 5K, and Bands pins sit close together.
Directions: South River Farm, Court Square in Harrisonburg, James Charles Winery, Ting Pavilion, Dairy Market, the Sunday gazebo, Westover Park, Bridgeforth Stadium.
Halloween plans close to home
Harvest of Horror
Choose the farm when you want the dark. South River Farm says Harvest of Horror is a haunted trail and corn maze, every Friday and Saturday from September 26 through October 31, 2026. That covers October 23 and 24. The address is 2310 Rivermont Drive, Front Royal, VA 22630, phone (540) 551-0487. The farm page does not list a clock or a price.
The town calendar does list the clock. Friday and Saturday are each 7:00–10:00 p.m. at that address. Both pages point at a ticket link and still do not print a price. The town's line is the packing note I would read first: when the sun goes down, the walk goes through dark woods and tall corn.
Skeleton Festival
Choose downtown Harrisonburg when the costume is the point and you want to skip a ticket. Skeleton Festival is Saturday, October 24, 2026, 1–5 p.m., and the page calls it a free community festival. Trick-or-treating at downtown businesses runs those hours. Noon to 1 p.m. adds a sensory-friendly hour at Shops at Agora for neurodivergent children and their caregivers, and a separate free trick-or-treat hour on Liberty and Mason, with the first 30 people at each participating stop. The costume contest is 3:30 p.m. on the Court Square lawn, and the page says it is open to all ages.
Main Street, from MLK to just before Gay Street, is closed 8 a.m.–6 p.m. The page says parking stays reachable from Mason and Liberty. If Saturday is for costumes, this is the one I would circle. It overlaps the winery, so it is one town or the other.
Other ways to spend Saturday
The Big Cheese
Choose Winchester when you want music, food, and a glass, and Harrisonburg can have the costumes. The winery events page lists The Big Cheese on October 24, noon–6 p.m., at 4063 Middle Road, Winchester, VA 22602, for $20. The ticket on that page includes entry plus one wine and cheese pairing at one of three winery tents. Phone (540) 931-4386.
Visit Winchester matches the date, hours, and address, then adds $20 in advance, $25 at the door, and children under 12 free. The ticket page showed no price on October 23, so open it before you count on a sale at the gate. Facebook and Instagram.Noon to 6 overlaps Skeleton Festival. Pick the town that matches the afternoon you actually want.
Charlottesville, two free afternoons that overlap
Charlottesville Parks and Recreation lists Monster Mash on Saturday, October 24, 2–4 p.m., at Ting Pavilion. The calendar does not give a street number. It is free, with a costume contest, and Downtown Mall trick-or-treat from 4:00–4:30 p.m. Phone 434-970-3260. Choose it for a short, free mall afternoon. Dairy Market lists Boo at the Moo the same day, 3–6 p.m., at 946 Grady Avenue. Admission is free, and the page asks for an RSVP. The afternoon is costumes, trick-or-treating, live music, face painting, balloon animals, and pumpkin painting, then an outdoor screening of Casper. Choose it when you want to stay through the movie. That 3 p.m. start covers the last hour of Monster Mash, so pick one.The 5K, then the bands
The Race to Beat Breast Cancer 5K is the early Saturday, if a run is the reason to be in Harrisonburg before the skeletons. The city page lists Saturday, October 24, 2026, 9:30–11:30 a.m., at the Community Activities Center / Westover Park. From October 10 through October 24 the individual rate is $40. Virtual is $30. RunSignUp, linked from that city page, says registration ends October 23, 2026, at 5:00 p.m. EDT, at those same prices, and it lists the place as 305 South Dogwood Drive, Harrisonburg. The city page also thanks people who already came, so on Friday I would trust the RunSignUp line for whether signup is still open. The city page says the proceeds go to the RMH Foundation at Sentara RMH Medical Center.
Parade of Champions is an all-day marching-band competition at Bridgeforth Stadium the same Saturday. Tickets are sold that day at Ticket Booth A. General admission is $20. Discounted admission is $15 for active or retired military, K–12 and college students, and seniors 65 and older, with the ID the page asks for. Children 3 and under are free. A wristband admits you for the day. The page does not print performance times. If the bands are the reason for the trip, give the stadium the day. Phone on the page: 540-568-6656.The race ends at 11:30 a.m. and the festival's main hours start at 1 p.m. The stadium stays its own plan, because the page never names a start.
Sunday market
Choose Sunday when Saturday was enough and a slow grocery morning sounds better than another ticket. Downtown Front Royal, Inc. says Farm to Market on Main is every Sunday, May 2026 through October 2026, 9 a.m.–1 p.m., at the Main Street Gazebo, 317 East Main Street. October 25 is a Sunday in that range. No admission is listed. A tote at their table is $20, and the page says that money supports the market. The town calendar says the gazebo at Main and Chester, same hours. I would pin 317 East Main. Facebook.
Willing to drive farther?
| Event | When | Admission |
|---|---|---|
| Steven C. Wright book signing, Harpers Ferry | Sat 11 a.m.–4:30 p.m. | Free, RSVP |
| HarvestFest, Lewis Ginter, Richmond | Sat 10 a.m.–2 p.m. | Included with garden admission |
| Plant Native!, Dorey Park, Henrico | Sat 9 a.m.–1 p.m. | Not listed |
| Hirshhorn Teen Studio, Washington | Confirm on the organizer page | Confirm on the organizer page |
The Harpers Ferry signing is the quiet choice. The Appalachian Trail Conservancy lists Steven C. Wright on October 24, 11:00 a.m.–4:30 p.m., at 799 Washington Street, Harpers Ferry, WV 25425. It is free, and the page asks for an RSVP. The book is *The Weight I Carried*. Copies are sold on site, and the page says 15 percent of those proceeds go to the Conservancy. Choose it when you want an author hour and the costume crowds can stay in town. Harpers Ferry map.
HarvestFest is the garden day. Lewis Ginter lists Saturday, October 24, 10 a.m.–2 p.m., included with regular garden admission, at 1800 Lakeside Avenue, Richmond, VA 23228. Storytime is at 10 a.m. The admission page lists $24 for adults, $20 for seniors 65 and older or military, first responders, and full-time educators, $14 for ages 4–17, and free for age 3 and under and for members. Museums for All on that page is $1 for adults and free for up to six youth, with the card the page names. That same page says some special events use another ticket. HarvestFest's own page says this one is included. Choose it when you want crafts and a story hour and you can give the morning to the drive. Richmond map.
Plant Native! is the plant day. Henrico's page lists Saturday, October 24, 2026, 9 a.m.–1 p.m., at Dorey Park, a celebration of native plants and the local groups that look after them. Admission was not listed on the page on October 23. Dorey Park map.
Time and price for that studio were not available on October 23, 2026. They stay on the organizer page. If a teen in the car wants a museum studio hour, read that page before you commit the drive. Washington map.
Prefer the mountains
If the towns feel like too many clocks, take the ridge. The Skyline Drive fall-color guide already has the entrances, the fee, and where to fill the tank. I photographed the red maple near Kennedy Peak on October 17, 2026. The turn and the parking note are in the Kennedy Peak hike.
Overnight and road-trip planning
Lodging and the fuel apps belong in the same decision: are you coming home, or is Saturday going to run late?
A Front Royal room, if the night refuses to end: Expedia (paid link). An RV park search: AllStays (paid link).
Before a longer day I check station prices in town. GasBuddy (paid link, referral link), code EM4F5VF. Upside (paid link, referral link), code LISA42442, for cash back on a fill-up. Savings and cash back vary by offer.
Drive times from Luray, calculated October 22, 2026. One public driving-route calculation that day, not live traffic: Front Royal about 37 minutes, Harrisonburg about 47, Winchester about 71, Charlottesville about 94, Harpers Ferry about 102, Washington about 122, and Richmond about 165. Use the map links the morning you leave.
More from the valley, and the shop
The Apple House in Linden is the donut stop on the way toward the Drive. Valley prints are in the shop. The backpack notes, if the day turns into photographs, are in the gear post. The fall-color guide and Big Meadows are the longer ridge reads. More valley writing lives on Foster Your Journey.Details were checked against the organizer pages on October 23, 2026. The Hirshhorn page did not open that day. Hours and prices move. Check with the organizer before you leave. After Sunday, October 25, 2026, these hours belong to that weekend.
Check Journey if you want a seasonal note.
Which plan are you taking?