May arrives with one of Vermont’s most beloved civic traditions, a fly fishing festival celebrating its 5th anniversary on the Battenkill, classical music in Randolph, and the Mad River Valley doing what it does every weekend — throwing a better party than most places manage all year.
Friday, May 1
Battenkill Fly Fishing & Arts Festival Kicks Off | Arlington | All Weekend Vermont’s newest Signature Event opens Thursday and runs through Saturday on the banks of one of the most storied trout rivers in the Northeast. Friday is your chance to get in before the weekend crowds — free casting clinics with Orvis instructors, the Mountains, Valleys and Rivers art exhibit at the historic Watkins House, and the Lawson’s Microbrew Tent. This is its 5th anniversary and the thing has grown into a full-on celebration of fly fishing, art, music, and river stewardship. Proceeds support the Battenkill Fund. Worth the drive to Arlington. vtflyfest.com
GreggFest | Catamount Arts, St. Johnsbury | 7pm Two-day music festival kicks off Friday night in the Northeast Kingdom. Catamount Arts runs one of the best small venues in the state — if GreggFest is on their calendar, it’s worth your attention. catamountarts.org
Thea Alvin — William Eddy Lecture & Gallery Reception | Catamount Arts, St. Johnsbury | 6pm Artist talk and gallery opening before the evening’s festivities. Good Friday night double-header in St. J if you’re heading up for GreggFest anyway.
Rock Voices Spring Concert | Centre Congregational Church, Brattleboro | Evening Community choir doing what community choirs do best — filling a beautiful old church with voices. Free and open to the public in downtown Brattleboro. brattleborochamber.org
The Rambunktious Ragamuffins | Marigold, Brattleboro | 8pm Swing and hot jazz on the Marigold stage in Brattleboro. Good Friday night option if you’re in Windham County and want something lively.
Family Fridays | Big Picture Theater, Waitsfield | 4:30–6pm Adults unwind with cocktails, kids do creative activities. The Mad River Valley’s most civilized Friday institution. bigpicturetheater.info
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Saturday, May 2
Vermont Green Up Day | Statewide | All Day | Free The 55th annual Green Up Day — Vermont’s great civic ritual. Over 25,000 volunteers typically fan out across the state to clean up roadsides, parks, and waterways. Last year they pulled 427 tons of trash and 14,300 tires off Vermont’s roads. Your town is organizing something — show up, grab a bag, put in a couple of hours. This is one of those Vermont things that actually works. Find your local effort at greenupvermont.org
Battenkill Fly Fishing & Arts Festival | Arlington | All Day The main day of the festival. Casting championship, live music, art exhibit, Lawson’s beer, kids’ activities, and legendary instructors on the water. This is the one. vtflyfest.com
Vermont Philharmonic: Sparkle of Spring | Chandler Center for the Arts, Randolph | 4pm Conductor Lou Kosma leads the Vermont Philharmonic in a program anchored by Beethoven’s Violin Concerto in D major, performed by acclaimed violinist Arturo Delmoni. Chandler keeps punching above its weight class — this is world-class classical music in a gorgeous 800-seat hall in central Vermont. Don’t sleep on it. chandler-arts.org
Southern Vermont HomeBrew Festival | Bennington | Noon–4pm Home-brewed beverages, food trucks, vendors, and live music in Bennington. Local brewers showing their work — unpretentious, fun, and exactly the kind of Saturday afternoon that makes Vermont Saturdays worth protecting. bennington.com
Bear Fair — Mad River Valley Bear Initiative | Mad River Valley | 10am–2pm Community event raising awareness about Vermont’s black bear population and how to coexist with them. Educational, outdoor, free. Good family Saturday morning in the Valley. madrivervalley.com
Green Valley Rally | Mad River Valley | 8am–2pm Morning community event in the Valley — get out early and make a day of it. madrivervalley.com
Kentucky Derby Watch Party | Mad River Valley | 5–8pm The Valley knows how to transition from a civic morning to a festive evening. Hats encouraged. madrivervalley.com
Just Desserts Benefit Concert | 24 Main Street Community Building, Saxtons River | 7pm Music, community, and dessert for a good cause in Saxtons River — one of those Windham County events that sounds low-key and ends up being the best thing you did all weekend. brattleborochamber.org
Introduction to Glassblowing | Fire Arts Vermont, Brattleboro area | Saturday Always wanted to try it? Here’s your shot. Hands-on intro class in the Brattleboro area. ibrattleboro.com
From the Vine to Vermont | The Landgrove, Landgrove | Evening One-night-only curated wine pairing dinner at this mountain destination in the southern Vermont hills. Intimate, elevated, beautiful setting. vermont.com
Sunday, May 3
Sunday Sessions: Jaded Ravins | Lawson’s Finest Taproom, Warren | 3–5pm Live music at Lawson’s on a Sunday afternoon. This is one of Vermont’s great recurring pleasures — world-class beer, local music, and the Mad River Valley doing its thing as spring takes hold. Free. lawsonsfinest.com
Iconic Sunday — Sugarbush & Ikon Passholder Night | Sugarbush, Warren | 4–8:30pm The ski season is still technically alive at Sugarbush. If you’ve got an Ikon Pass, this is your Sunday night. sugarbush.com
Green Up Day, a fly fishing festival on the Battenkill, Beethoven in Randolph, and the Mad River Valley running wide open — May in Vermont doesn’t ease in, it arrives.
Dave Soulia | FYIVT
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