alloween falls on a Saturday this year, which means the whole state gets a three-day run at it instead of one frantic school night. Free horror movies, a walking parade, a haunted disco, and on Sunday someone in Brattleboro will teach you trapeze for nothing. The couch will still be there Monday.
🏁Weekend Spotlight: Pentangle’s Horror Film Festival
Pentangle Arts takes over Woodstock Town Hall Theatre on the Green for three days of cult favorites and Halloween classics — movies made to be watched with a crowd that screams on cue. Tickets are $10, costumes are welcome, and there are seasonal concessions.
Friday, October 30: Little Shop of Horrors at 7 p.m., then Carrie at 10 p.m. for the people who don’t need sleep.
Saturday, October 31: Monster House at 2 p.m. for the kids, The Craft at 7 p.m., and Scream at 10 p.m. to close out Halloween proper.
Sunday, November 1: Labyrinth at 2 p.m. — the gentle landing.
Friday, October 30
An Edgar Allan Poe Halloween starts at 7 p.m. at Lost Nation Theater in Montpelier’s City Hall Auditorium Arts Center, a fundraiser of spine-tingling tales with decorations, treats, and a costume contest. Stoph Scheer hosts, with Kim Bent, AnnaMaria DiPietropaolo, William Pelton, Maura O’Brien, and Mark Roberts doing the reading. Tickets are $20 in advance, $25 at the door, and a digital version streams through Sunday if you’d rather be haunted at home. Lost Nation Theater
Sleepy Hollow The Musical opens Friday at the Barre Opera House, with four shows through Sunday afternoon. Acorn Youth Arts turns Washington Irving’s headless-horseman tale into a rock musical that mixes film with live performance. Come in costume — there’s trick-or-treating, door prizes, and raffles, and admission is pay what you can (suggested $25), no one turned away. Barre Opera House
Live Band Karaoke and Costume Contest runs 6 to 8 p.m. at Lawson’s Finest Taproom in Waitsfield, with The Karaoke Bandstand backing you up. A real band behind you means you can’t blame the track. Lawson’s Finest Liquids
Almost, Maine plays at 7:30 p.m. in the Seeler Studio Theatre at Middlebury College’s Mahaney Arts Center. Professor Alex Draper directs John Cariani’s comedy about romance going sideways under the northern lights in a town that doesn’t quite exist. Tickets run $5 to $15. Addison County Chamber of Commerce
Night of the Living Dead screens free at 7:30 p.m. at Catamount Arts Center in St. Johnsbury. George A. Romero’s 1968 farmhouse siege basically invented the modern zombie, and it’s part of Eric Hauter’s monthly horror series. Free, in the dark, with strangers — exactly how Romero would want it. Catamount Arts
Real Big Blues at the Kingdom Brewery goes 6:30 to 9 p.m. at Kingdom Brewery on Coburn Hill Road in Newport. Brews and blues, live, up where the weekend starts early. Discover Newport
MINC: A Halloween Concert & Costume Party runs 7 to 9 p.m. at Artistree Community Arts Center in South Pomfret. MINC is an eight-piece band of Vermont high schoolers playing soul, funk, and pop in the Amy Winehouse and Stevie Wonder vein, and there’s candy and maybe a costume contest. $10 for students, $20 for adults. Woodstock Area Chamber of Commerce
Saturday, October 31
Halloween Bash fills the Orleans County Fairgrounds in Barton from 1 to 4 p.m. — trunk-or-treat on the track, a hay maze, farm-themed entertainment, and it’s completely free. First year for this one, so get in on the ground floor. Discover Newport
Artist Festival at Reading Greenhouse runs 10 a.m. to 4 p.m. at Reading Greenhouse & Farm Market on Route 106 in Reading. More than 45 local artisans, a quilt exhibit, live acoustic music, tarot and Reiki demos, and farm food. Admission is free, there’s a door-prize raffle, and if you miss it, it comes back November 7. Woodstock Area Chamber of Commerce
Halloween on the Hill runs 2 to 5 p.m. at the Southern Vermont Arts Center in Manchester: a magic show, spooky stories with the Kinhaven Quartet, fortune telling, face painting, and a make-your-own potion station. There’s a costume parade with prizes and barbecue from curATE Café. Free, but register — registrants get entered in a raffle. Bennington Banner
North Bennington Halloween Parade steps off at 3 p.m. from the Vermont Arts Exchange front yard at 48 Main Street, winds down to Pangaea, around the fountain, back up Main, and right on Houghton to Lions Park. The after-party there has live music, refreshments from the Norshaft Lions, and the costume awards. Walking parade only — leave the float plans at home. Bennington Banner
Halloween — the 1978 original — screens free at 7 p.m. at the Paramount Theatre in Rutland, doors at 6:30, no ticket required. Jamie Lee Curtis, Donald Pleasence, Michael Myers, a big dark room on Halloween night. That’s the whole pitch. Paramount Theatre
Halloween-o-thon 2026: Leaf Creepers runs 6 to 7:30 p.m. at JAM – Junction Arts & Media in White River Junction, a screening and awards night for short films on this year’s “somebody’s watching” theme. It wraps just before the Gory Daze Parade, so show up in costume and walk out into it. Registration required. JAM
Cirque Du Funk – Haunted Disco goes from 8 p.m. to 1 a.m. at afterthoughts in Waitsfield, with a live set from Ryan Dempsey, Lee Ross, and Bill Love, then DJ Tobin Ellsworth. Promised: spooky shenanigans and wild visuals. Presented with The Black Kitty. Mad River Valley Chamber
Sunday, November 1
Free Community Day at the Vermont Circus Festival kicks off at 9 a.m. at the New England Center for Circus Arts in Brattleboro — free circus classes for youth, adults, and the Silver Circus crowd, with clowning, performances, and trapeze at your own speed. It’s free thanks to the Brattleboro Town Arts Fund, but pre-registration is required. The festival keeps going through November 8. New England Center for Circus Arts
Vermont 10 Miler loops out from the Mayo Farm Event Fields in Stowe, up West Hill Road and home along the last three miles of the Stowe Recreation Path, with aid stations every two miles. No pets, no strollers. Run it, or stand at the finish and clap for the people who did. Go Stowe
📌Heads-up: Keys to Hope Gala, Friday, November 13
The Dodge House holds its first annual Keys to Hope Gala on Friday, November 13, from 6 to 10 p.m. at Rutland Elks Lodge #345 — an evening of community, connection, and giving back, with JT Dodge giving the keynote. Every ticket helps the Dodge House keep providing transitional housing and support to veterans working toward permanent housing, and Vietnam Veterans of America Chapter 1 of Rutland is a Gold Sponsor. Tickets are $50 per person, online or at the Dodge House office during business hours. Get tickets
Nine counties, one Halloween, and three whole days to wear the costume. Go get your money’s worth out of it.
Feature photo by Colton Sturgeon on Unsplash