October 8, 2026
Halloween in downtown Woodstock now runs over two nights, each with its own address. On Friday, Oct. 30, Ghouls Night Out sends trick-or-treaters through the shops and restaurants of Main Street from 4 to 7 p.m. On Saturday, Oct. 31, the City of Woodstock hosts its free Halloween Skelebration from 4 to 8 p.m. at the Northside Hospital-Cherokee Amphitheater, 101 Arnold Mill Road.
This calendar is new. Until 2024, the city's Halloween night was a walk on a single trail. In 2025 it moved to a park with its own name, and this year the date falls on a Saturday. The two events now sit on back-to-back nights, and Friday has more going on than Halloween itself.
Two years ago, the city's Halloween event was the Halloween Trail of Tricks and Treats on Rubes Creek Trail. The 2024 version was free and ran 5 to 9 p.m. on Oct. 31. It was a 1.4-mile round-trip walk with music, characters, games, crafts and treats handed out by vendors along the way, and flashlights were encouraged.
In 2025 the trail was under construction, so the city moved the event to the amphitheater and renamed it. The Cherokee County Chamber of Commerce release from Oct. 22, 2025, explains the change. Woodstock Special Events Coordinator Marybeth Stockdale described it this way:
"We're excited to reimagine this much-loved Halloween tradition in a new setting. The Halloween Skelebration gives families a safe, fun, and memorable way to celebrate, with even more room for activities and community togetherness."
For 2026 the city has kept the Skelebration at the amphitheater. The 2025 Skelebration also fell on a Friday, Oct. 31. This year Halloween is a Saturday, so the city event lands the night after the Main Street trick-or-treat. A family can now do both without picking one.
The 2026 flyer and the city's event listing describe trick-or-treating throughout the park, plus carnival games, mini golf, crafts and activities, pumpkin inflatables, food vendors, music, giant bubbles and playful spooky displays. Mystical Parties Entertainment is listed for character performances and children's dance parties. Admission is free, it's open to all ages, and parking is free.
The current official materials don't mention a costume contest, a trunk-or-treat or a movie, and they don't name a band. The city also hasn't posted a rain plan specific to this event. Its general special-events notice says extreme weather can change an event's date, time or location, and it points people to the city website and social media for updates. If the forecast looks rough on the 31st, check there that afternoon.
Saturday has the one big city event, but Friday stacks several things on the same evening downtown. Here's Oct. 29 and 30 in order:
So a family can trick-or-treat until 7, and the 6 p.m. double feature is already running a block or so away for the older kids and adults. Rocky Horror covers the later crowd.
Visit Woodstock doesn't describe a storefront marker or a set route. Its participant list is the map. The 2026 list includes:
One stop works a little differently. Antiques by Samson & Delilah says its store will be closed during event hours, but it will still hand out treats for kids along with 10% discount coupons for a later visit.
Both nights fall inside the Scarecrow Invasion, which has been building since the end of September. Displays went up Sept. 28 through Oct. 2, stay up through October, and have to be removed by Nov. 3. Visit Woodstock says there are hundreds of them across the downtown district, made by businesses, individuals and nonprofits. It hasn't published an exact 2026 count.
Getting a spot isn't easy. Registration has to be done in person, the 2026 event is full, and Visit Woodstock recommends getting in line before 10 a.m. on registration day. Businesses pay $100 and nonprofits pay $50. A 2026 City Lifestyle feature says individuals can also enter for $50.
This year's scavenger-hunt clue sheet spreads the search across downtown. Several clues are at the Park at City Center, and others point to Adair Park, Chambers, JDs on Main, the corner of Main Street and Towne Lake Parkway, Depot Square, and a display near Rreal Tacos. One clue mentions a scarecrow tied to a Woodstock Elementary class, and another mentions a club's display. You can work through the sheet any day this month.
Votes cost $1 each. You can vote at the Visitors Center, 8588 Main Street, which is open 10 a.m. to 5 p.m. Monday through Saturday and noon to 5 p.m. on Sunday. Some businesses with scarecrows also take votes in their stores for their own entry. The winner gets bragging rights and a trophy. Proceeds go to INSeason, Visit Woodstock's downtown design committee.
The Visitors Center is also on the Ghouls Night Out list. If you haven't voted by Oct. 30, you can stop in between treat stops that Friday.
Woodstock Arts has events most weeks this month, so there's something to do downtown on the in-between nights:
Saturday mornings have their own routine. The Farm. Fresh. Market. runs from 8:30 a.m. to noon at Market Street and Reformation Brewery's Backyard every Saturday through Dec. 19. On Oct. 31, you could go to the market in the morning and the Skelebration in the afternoon.
The season ends Nov. 7 and 8 with the free Día de los Muertos Festival at the Woodstock Arts Event Green, 113 Elm St. Hours are 9 a.m. to 6 p.m. Saturday and 10 a.m. to 5 p.m. Sunday. The 2026 lineup includes Sofi G, Mariachi Buhos de Oro, a salsa dance class, lotería and a movie, along with local art and food vendors. Visitors can add something to the community ofrenda in honor of loved ones who have died.
This year's festival is a week later than last year's, which ran Nov. 1 and 2, 2025. Woodstock Arts is still accepting art, craft and food vendors, with applications due Oct. 15. Parking is free in the City Center East Parking Deck, which has more than 600 spaces, and in the lot next to Woodstock Arts Theatre.
Between the scarecrows going up and Día de los Muertos wrapping up, downtown has something on the calendar for about six straight weeks. Friday, Oct. 30, is the busiest single evening of that stretch.
If you spent a Saturday this month following scarecrow clues from Depot Square to Towne Lake Parkway and started wondering what the streets just off Main are like to live on, Kimberly Eslinger knows these blocks and is happy to walk them with you. Schedule a consultation, and bring your favorite scarecrow's name.
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