Memorial Day weekend doesn’t ease you in — it drops you into summer headfirst. From a 39th annual arts festival shutting down Bennington’s Main Street, to an inaugural food and wine festival anchored by The Equinox, to a 20-piece cosmic big band in a Mad River Valley movie theater and a free folk cult gathering in a gothic Brattleboro church, this is the kind of weekend Vermont was built for.
Friday, May 22
Don’t Let the Pigeon Drive the Bus! The Musical! | Spruce Peak Arts, Stowe, Lamoille County
TheaterWorksUSA’s touring production of Mo Willems’ beloved picture book hits the Spruce Peak stage Friday at noon — songs, feathers, and a bird who just wants a chance. If you’ve got kids in the 3–8 range and you haven’t already penciled this in, consider it penciled. sprucepeakarts.org
Manchester Food & Wine Festival: VIP Preview Soirée | The Equinox, Manchester, Bennington County
The inaugural Manchester Food & Wine Festival opens Friday evening at 6:30 p.m. with a VIP Preview Soirée at The Equinox — a ticketed, smaller-crowd kickoff before Sunday’s Grand Tasting. Vermont’s finest culinary voices, set against the mountain backdrop Manchester does better than anywhere. The full festival runs all three days; Friday night is your early-bird look at what they’re working with. vermontfoodfestival.com
Saturn People’s Sound Collective | Big Picture Theater & Cafe, Waitsfield, Washington County
Here’s the show of the weekend that nobody outside the Mad River Valley may know about — and it should be packed. Saturn People’s Sound Collective is a 20-piece Vermont ensemble at the intersection of creative big band, postmodern rock, and outer space, featuring some of the finest musicians in the state. Special opener Highland Jazz. Friday at 7 p.m. at the Big Picture in Waitsfield — a beloved community cinema-and-cafe that doubles as one of Vermont’s best small music venues. bigpicturetheater.info
The Others (Film) | Catamount Arts, St. Johnsbury, Caledonia County
Catamount Arts’ monthly horror film series — curated and hosted by film podcaster Eric Hauter — screens Alejandro Amenábar’s The Others Friday at 7:30 p.m. The 2001 Nicole Kidman gothic ghost story is set in a fog-soaked Jersey mansion, built entirely on atmosphere and dread, and holds up better than most horror from that era. Admission is free. catamountarts.org
Crunk Witch w/ Night Protocol & Hexenclub | The Monkey House, Winooski, Chittenden County
Friday night at the Monkey House gets loud, late, and a little weird — Crunk Witch headlines with Night Protocol and Hexenclub (DJ set) starting at 8:30 p.m. Exactly what a Memorial Day Friday deserves. monkeyhousevt.com
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Saturday, May 23
Memorial Day Weekend in Woodstock | Downtown Woodstock, Windsor County
Woodstock’s Memorial Day parade steps off Saturday at 10:30 a.m. — one of those small-town Vermont traditions that still feels genuinely earned. Around it, the downtown Sidewalk Sale runs 9 a.m. to 5 p.m. with live music from 10 a.m. to 5 p.m., and the Woodstock Garden Club holds its plant sale from 8 a.m. to 1 p.m. on The Green. The Billings Farm & Museum is open for the season, as is the Marsh-Billings-Rockefeller National Historical Park. If you’ve been sleeping on a spring day trip to Woodstock, this is the weekend that tips the hand. woodstockvt.com
Mayfest Arts & Crafts Festival | Downtown Bennington, Bennington County
Now in its 39th year, Mayfest takes over Bennington’s Main Street — Four Corners to Valentine — Saturday from 10 a.m. to 5 p.m. with more than 130 curated vendors, 10-plus food trucks, and live music on two stages all day. The lineup includes All Ten & John, Mister Sister, Olson Brothers Band, Sky Allan, Buck2Fifty, and more. There’s a full Kids’ Zone running 11 a.m. to 4 p.m. with free activities, and a 501st Legion appearance if you know, you know. Admission is free. This is one of Bennington’s signature events and it delivers every single year. happyvermont.com/event/mayfest-arts-crafts-festival-in-bennington
Manchester Food & Wine Festival: Saturday Events | Manchester & Pawlet, Bennington & Rutland Counties
Saturday, the Food & Wine Festival fans out across the region. The standout: a self-guided pasture walk and cheese tasting at Woodlawn Creamery in Pawlet — a working farm in Rutland County where you can taste what Vermont cheese is actually supposed to taste like. Back in Manchester, there’s a wine-paired lunch at the Southern Vermont Arts Center and a free brewery tour at Lost Marble Brewing. Plus vermouth and cider flights at Local Maverick. The full weekend is built for people who take food seriously without taking themselves too seriously. vermontfoodfestival.com
Von Trapp Brewing Bierhall Summer Music Series — Opening Weekend | Stowe, Lamoille County
The von Trapp Bierhall Music Series officially opens for summer this weekend (Saturday and Sunday), kicking off what becomes a full season of Saturday-evening concerts in the Biergarten through Columbus Day. This opening weekend features live performances, with the full summer lineup including Uprooted with Michael Glabicki of Rusted Root, Dwight & Nicole, and Blues Over Easy. Pair it with a German-style lager poured by the people who actually know how to make one, and you’ve got a Stowe Saturday sorted. gostowe.com
Mental-Drift: Dredd Foole, Glenn Jones, Allysen Callery, Liam Grant, Lys Guillorn | Epsilon Spires, Brattleboro, Windham County
This one’s for the people who know. Epsilon Spires — a 19th-century High Victorian Gothic church in downtown Brattleboro — hosts a deeply unusual Saturday gathering under the “Mental-Drift” banner: Dredd Foole (free folk legend who moved to Brattleboro decades ago and never really left the underground), Glenn Jones (master of American primitive guitar, making his first Brattleboro appearance in years), and a supporting cast that includes Allysen Callery, Liam Grant, and Lys Guillorn. If you’ve ever been to a show at Epsilon Spires, you know the room makes everything better. If you haven’t, this is an argument to start. epsilonspires.org
Seth Yacovone Band w/ Phantom Suns | The Monkey House, Winooski, Chittenden County
Seth Yacovone has been a fixture of Vermont’s live music scene for three decades — his trio an eclectic, improvisational blend of blues, rock, funk, Americana, and whatever else the room calls for that night. Saturday at the Monkey House starting at 7:30 p.m., with Phantom Suns opening. It’s the right way to spend a Memorial Day Saturday night in Chittenden County. monkeyhousevt.com
Sunday, May 24
Manchester Food & Wine Festival: Grand Tasting | The Equinox, Manchester, Bennington County
The festival’s main event: the Grand Tasting at The Equinox Sunday afternoon, with an extensive selection of local, regional, and international wines, gourmet bites from award-winning regional restaurants, Vermont small-batch producers, artisan vendors, live music, and hourly raffle drawings. This is the capstone of three days of serious eating and drinking in the shadow of Mount Equinox — and from everything we’ve seen of the lineup, they’ve done this right. vermontfoodfestival.com
Stowe Dance Academy: Evening of Dance | Spruce Peak Arts, Stowe, Lamoille County
Stowe Dance Academy brings its spring showcase to the Spruce Peak stage Sunday with two performances: 2 p.m. and 6 p.m. Dancers ages 5–18 from Stowe, Morrisville, Elmore, Waterbury, the Mad River Valley, and beyond perform in Lyrical, Jazz, Contemporary, Tap, Musical Theater, and Hip Hop. A community event as much as a performance, and one of those afternoons that reminds you why local arts infrastructure matters. sprucepeakarts.org
Von Trapp Brewing Bierhall Music Series | Stowe, Lamoille County
The series continues Sunday afternoon — second day of opening weekend in the Biergarten at von Trapp. Grab a Helles and find out what summer in Stowe is going to sound like this year. gostowe.com
Memorial Day weekend in Vermont is less about slowing down and more about finally remembering what “outside” is for. Go find out.
Dave Soulia | FYIVT
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