A full day of live animals, demonstrations, and hands-on activities for kids, with presentations from nature organizations across the region. Food available to purchase and admission is by donation, which makes this an easy yes for families.

The fifth annual pilgrimage walk covers the Deerfield River Valley over two days, starting in Wilmington on Saturday morning and finishing at the Ephesus House in Jamaica on Sunday afternoon. Distances run anywhere from 2 to 25 miles, with refreshment stops, talks, a Saturday dinner and a closing barbecue along the way, and rides available on the route if your legs give out first. Registration is required in advance, so sort that before you arrive.

A car show on the Brattleboro Common run by the local Rotary Club, with food, awards, and a 50/50 raffle. Proceeds support the Windham County Career Center auto tech program. Worth pairing with an afternoon poking around downtown Brattleboro.

Live music on the mountain-view patio, free and five minutes away.

Make the drive down for one of American songwriting's true originals. Three-time Grammy winner Lucinda Williams brings her band to the Hunter Center behind her eighteenth studio album, World's Gone Wrong, a set of urgent, unflinching songs written in a burst of collaborative energy. Time Magazine once called her America's best songwriter, and 45 years into her career she still plays like she has something to prove. Tickets run $59 general admission, $99 preferred.

Local arts, crafts, produce, and wellness offerings gathered for an afternoon in Jacksonville. A low-key alternative if the Oktoberfest crowds aren't your speed.

Mount Snow's take on the world's most famous beer festival, now in its 28th year. Admission is free and beer tickets get you pours at winter hangouts like Cuzzins, Station Tap Room, and 1900' Burger, all transformed for the occasion.

Live music on the patio to close out Oktoberfest day.

Devendra Banhart, Gyan Riley, and Noah Georgeson bring Hug to the Hunter Center stage. On paper it's a guitar trio, but the record wanders somewhere stranger and warmer than that, weaving folk, ambient, and experimental threads with field recordings and Sanskrit chant. Written and recorded in three weeks, it plays like three old friends thinking out loud together. Tickets are $46 advance, $56 week-of, $76 preferred.

Fifty-four years running and still entirely volunteer-run, this is the postcard version of a Vermont fall weekend. A juried arts and crafts show fills the village green, local specialty foods turn out in force including apple pie people drive for, and there's a raffle, kids' activities, and live entertainment. Peak foliage backdrop, leashed dogs welcome.

The second Oktoberfest Saturday, running an hour later than the first. Free admission, beer tickets sold separately, and peak foliage weekend on the mountain.

Ride the gondola to the summit, climb the Stratton fire tower for a look at the whole valley in color, then come back down for the BrewFest. Vermont beer, a chili competition, live music, and a family-friendly setup all day. Note dogs aren't allowed at this one even though Stratton is usually leash-friendly.

The last Saturday of the patio series before the season closes out. Catch it while the mountain views still have color in them.

Three days of readings, panels, and author conversations spread across downtown Brattleboro venues. The festival has hosted more than 900 authors over its run, including Pulitzer, National Book Award, Newbery, and Caldecott winners. Daytime events have historically been free with no registration, which makes it easy to drop in for one session or spend the whole day. Dogs not permitted.

NPR called them indie rap's favorite friendship, and they're bringing it to the Hunter Center for one night behind their collaborative album Pompeii // Utility. Earl Sweatshirt has spent over a decade building a catalog of dense, introspective, unmistakably his own records, and MIKE matches him step for step. With support from harrison (SURF GANG) and Anysia Kym. Tickets are $51.50 general admission, $88.50 preferred.

Only in Vermont does a root vegetable get its own festival. The Gilfeather was first cultivated right here in Wardsboro and became the official Vermont State Vegetable in 2016. The Trustees of the Wardsboro Library run the whole thing on volunteer power, selling Gilfeather soup, turnips by the pound, seeds, and souvenirs. Genuinely charming, genuinely strange, and twenty minutes up Route 100. Dogs not permitted.

The museum stays open late just for families. Wander select exhibitions after hours, catch live music and dance performances, make art, get faces painted, and take on the Museum of Mysteries Quest, working together to hunt down clues in the galleries and earn your own artist kit. Food and giveaways too. Free, with a suggested $5 donation. RSVPs are encouraged but not required.

Detroit-raised bassist and composer Endea Owens brings her band to the intimate Club B10. A Juilliard grad mentored by Ron Carter, she spent years in the house band on the Late Show with Stephen Colbert and has picked up an Emmy, a Grammy, and a Peabody along the way, with credits spanning Jon Batiste, Solange, and Wynton Marsalis. Her own music, heard on the 2023 debut Feel Good Music, lives up to the title. Tickets are $36 advance, $46 week-of, $56 preferred, $20 student.

Film critic A.S. Hamrah sits down for a conversation about movies, filmmakers, and the state of cinema in 2026. He writes for the New York Review of Books, n+1, The Nation, and the Criterion Collection, and his two recent books are bestsellers at the museum's R&D Store, where this takes place. Novelist Elif Batuman has said his writing makes art and life feel less lonely. Just $5 in advance, and free for members.

The oldest continuing craft tour in the country, running every Thanksgiving weekend since the late seventies. Follow the map through the hills to open studios of painters, jewelers, potters, weavers, glassblowers, a cheesemaker, a woodworker, an aromatherapist, and a winery. Many artisans demonstrate their work. Start at Putney Mountain Winery on Bellows Falls Road for the preview exhibition and maps. Buy direct from the person who made it.

Wander into the working studios of MASS MoCA's current artists-in-residence for snacks, conversation, and a look at what's being made right now. Studios are spread across Building 13, just off the main visitor lot, and Building 34, across the courtyard from Bright Ideas Brewery. Free and open to all, no ticket needed.

Spend an evening in MASS MoCA's Kidspace learning to mend. Jena Duncan and Elsa Cousins from Swanson's Fabrics Stash House lead a relaxed session in textile repair, embroidery, and small-scale weaving alongside museum educators. Bring a piece of clothing that needs fixing and walk out knowing how to fix it, or skip the repair and try your hand at weaving, adding to the community project on view in the galleries. No sewing experience needed and all materials are included. Refreshments available from the museum bar. $30.