Two events dominate this weekend and both are worth planning around. Bookstock brings 12,000 used books and a lineup of nationally recognized authors to the Woodstock green, while Music on the Mountain at Okemo draws some serious talent for a substance-free festival benefiting Trey Anastasio’s recovery foundation. The rest of Vermont fills in nicely around the edges.
Friday, May 15
Bookstock: Vermont Festival of Words Opens | Woodstock | 1–5pm (Friday) | Free One of the great Vermont literary weekends kicks off Friday afternoon on the Woodstock green with the Used Book Sale — 12,000 volumes, one price, first come first served. The full festival runs through Sunday with author readings, master classes, poetry events, and programming for kids. This year’s lineup includes Katherine Arden, Patrick Bringley, Gesine Bullock-Prado, and Amity Gaige. Friday evening opens at Artistree with a panel of Vermont Book Awards finalists. Free to attend; some ticketed events. Full schedule at bookstockvt.org
Music on the Mountain BIG Weekend Kicks Off | Ludlow | Evening The three-day weekend supporting Divided Sky Foundation — Phish guitarist Trey Anastasio’s residential recovery retreat — gets going Friday night with a Campfire Jam featuring Anders Osborne, Jackie Greene, and Daniel Donato performing in-the-round, joined by the Trombone Shorty Foundation Brass Band. Intimate, acoustic, and a hell of a way to open a festival. musiconthemtn.com
Comedy Play Fest | Grange Hall Cultural Center, Waterbury Center | 7:30pm | $20 suggested Three-night comedy theater run in Waterbury Center, continuing from last weekend. Friday and Saturday nights at 7:30, Sunday matinee at 2pm. Local theater at its most unpretentious. montpelieralive.com
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Saturday, May 16
Music on the Mountain | Okemo Mountain Base, Ludlow | Noon–8pm The main event. Anders Osborne, Jackie Greene, Eggy, LaMP, Karina Rykman, Daniel Donato, Natalie Cressman, and Jennifer Hartswick on one bill, all day, at the base of Okemo. Substance-free, family-friendly, and every dollar goes to Divided Sky Foundation. This is a genuinely good lineup for a genuinely good cause — not a combination you see every day. musiconthemtn.com
Bookstock | Woodstock Green | 9am–5pm | Free The main day. Author readings, master classes, the full book sale, kids’ events, and Cookstock — a sold-out five-course dinner pairing cookbook author Gesine Bullock-Prado with Woodstock Inn Executive Chef Matthew McClure. If you’re going to Bookstock, Saturday is the day. bookstockvt.org
Drew Hutson Rogers Band, Jaded Ravins & Sons of Williams | The Underground, Randolph | Doors 7pm, Show 7:30pm | $14 advance / $17 door The Underground in Randolph is one of Vermont’s best small listening rooms and this is a solid bill. Drew Hutson Rogers brings country-fried, Tom Petty-inspired originals up from Fayetteville, Arkansas, with Vermont’s own Jaded Ravins and Sons of Williams in support. All-ages, substance-free, and worth the drive to Orange County. Tickets at drewhutsonrogers.com
Comedy Play Fest | Grange Hall Cultural Center, Waterbury Center | 7:30pm | $20 suggested Night two. montpelieralive.com
Sunday, May 17
Music on the Mountain — Free Acoustic Brunch | Okemo, Ludlow | Morning The BIG Weekend wraps Sunday with a free acoustic brunch set featuring Murray’s Law (Brian Murray & Jimmy Law) and Vermont guitarist Evan Jennison. Free admission for the brunch — a low-key, beautiful way to close out the weekend at the base of Okemo. musiconthemtn.com
Bookstock Final Day | Woodstock Green | 10am–1pm | Free Sunday morning on the green in Woodstock — authors, books, and one of the prettiest village settings in Vermont. The festival closes at 1pm. bookstockvt.org
Early Birders Morning Walk | Birds of Vermont Museum, Huntington | 7–9am | Free Every Sunday through June, the Birds of Vermont Museum opens early for guided morning walks led by experienced local birders. Binoculars and good shoes required. Finish inside with bird-friendly coffee at the viewing window. Pre-registration helpful. On Sherman Hollow Road, 6 miles south of Richmond. birdsofvermont.org
Comedy Play Fest — Sunday Matinee | Grange Hall Cultural Center, Waterbury Center | 2pm | $20 suggested Closing performance of the run. montpelieralive.com
Woodstock has the books, Ludlow has the music, and a quiet road in Huntington has the birds at 7am. Vermont in May — there’s no excuse to stay inside.
Dave Soulia | FYIVT
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