Second weekend of August, and Vermont is running at full tilt. The Addison County Fair wraps up Saturday, Rutland's Art in the Park hits its 65th year, and there is more free live music scattered across this state than any one person can reasonably get to. Below is the honest version — verified, sourced, and organized so you can actually plan around it.

Friday, August 7

Addison County Fair & Field Days is in its home stretch at the Addison County Fairgrounds on Field Days Road in New Haven. Friday runs 8:30 a.m. to 11 p.m., $15 at the gate, with VTPA tractor pulls kicking things off at 8:30, the draft horse show at 9:30, pony pulling at 10, and WOKO arm wrestling — kids at 5, adults at 7 — before truck pulls at 6. This is still the largest agricultural fair in Vermont, and it is still the real thing: 4-H barns, working animals, and a midway that opens at noon.

Over in Waterbury, the 69th Annual Vermont Antique & Classic Car Meet takes over Farr's Field on Route 2 for all three days. The Vermont Automobile Enthusiasts run this one, and it is a proper meet — car corral, automotive flea market, vintage fashion judging, valve cover races. Judging happens Sunday, so Friday and Saturday are the browsing days.

Downtown Montpelier hosts the Montpelier Art Walk from 4 to 8 p.m., with more than twenty venues opening galleries and artist receptions along a free self-guided route. Details at montpelierartwalk.org. It runs the first Friday of even months, which is worth knowing if you miss this one.

Rutland closes its streets for Friday Night Live from 5 to 10 p.m. — Center Street and Merchants Row go car-free for an open-air street party with vendors, outdoor dining, and shops open late. August 7 is a street party night rather than a headline concert night, which frankly makes for a more relaxed evening. Details from Downtown Rutland.

In Manchester Center, Manchester StreetFest shuts down Main Street from 3 to 9:30 p.m., with the festival proper from 5:30 to 8:30 — live music from Ask Wanda plus food vendors. Listing via GNAT-TV. Twenty-five minutes south, the Bennington Museum hosts the Erin Harpe Country Blues Duo for Concerts in the Courtyard, 5 to 7 p.m., free, with the museum open late and food and drink for sale.

Art on Park brings artists, artisan vendors, and live music to Park Street in Stowe Village from 4 to 7 p.m., courtesy of Stowe Vibrancy — one of the last few Fridays in this summer's run.

Hardwick puts on the 6th Annual Community Farm & Food Celebration at Atkins Field, 3 to 6 p.m., alongside the weekly farmers market. Horse-drawn wagon rides, baby goats, live music, local food and drink, and no admission. Listing at the North Star Monthly.

Middlebury runs First Friday downtown from 5 p.m., with the Henry Sheldon Museum open free 5 to 7 and PhotoPlace Gallery holding an opening reception — details from Experience Middlebury. At 5:30, the Town Hall Theater puts Atom & the Orbits on the Tilly Stage at Maloney Plaza for the free 5 Fridays series. Bring a chair.

Down in Ludlow, the Jackson Gore Summer Music Series is free and outdoors in the courtyard from 5:30 to 8:30. And in Weston, the Weston Theater Company has RENT at Walker Farm at 7:30 p.m. — their 90th season, and the show runs all weekend.

Two quieter picks: Catamount Arts in St. Johnsbury screens Joe Dante's The Howling at 7:30 p.m., free admission, no catch. And in Warren, Phantom Theater hosts Bay Area contemporary company Randee Paufve Dance at the Edgcomb Barn, 8 to 9:30 p.m., Friday and Saturday both.

Saturday, August 8

The 65th Annual Art in the Park Summer Festival fills Main Street Park at the junction of Routes 4 and 7 in Rutland, 10 a.m. to 5 p.m. Saturday and 10 to 4 Sunday. The Chaffee Art Center has run this juried fine art and craft festival for six and a half decades — specialty foods, kids' activities, music, and a voluntary donation at the gate.

Twenty minutes north in Brandon, SolarFest: The Gathering runs 10 a.m. to dusk at the Solarfest Center on Steinberg Road. Workshops start at 10, music at noon, keynote at 5. Free entry, free camping, food trucks, vendors, kids' zone. solarfest.center has the schedule. For a sustainability festival this size to still be free says something about how it's run.

Up in Jay, the 22nd Annual August West Festival takes the town green next to the Jay Country Store from noon to 5 — a free Grateful Dead tribute with Dead Sessions Lite and Rick Redington & Tuff Luv, plus tie-dyeing, food, and craft vendors. Info via Jay Peak.

Poultney marks its 91st annual East Poultney Day on the East Poultney Green, 9 a.m. to 3 p.m., themed "Women in the Revolution" for America's 250th, with a keynote from historian Phyllis Chapman. The Poultney Area Chamber has details. Ninety-one years is not a small thing for a village that size.

The big ticket Saturday night is The Sound of Music In Concert at the Trapp Family Lodge Concert Meadow in Stowe, 7 to 9 p.m. — Lyric Theatre Company with the Vermont Symphony Orchestra, staged on the actual von Trapp property. Friday is already sold out; Saturday is your shot. Listing here.

Stratton Mountain hosts Neil Young tribute Harvest and Rust at the Main Base Area, doors 5:30 and music 6 to 8, $25 adults and $15 under 18 — via Stratton. Earlier the same day, guitarist John Hill plays the Hubert Haus at the summit, noon to 3, free once you're up there. Over at Magic Mountain in Londonderry, the Glen David Andrews Band brings New Orleans jazz and funk to the Black Line Tavern, 7 to 9 p.m., free — listing.

Randolph opens the Central Vermont Chamber Music Festival at Chandler Music Hall at 7:30 p.m. — Brahms, Glière, and Żeleński with Michael Roth, Arturo Delmoni, Peter Sanders, and Diana Fanning. $27 for adults, free for students, which is exactly the right pricing.

In North Hero, the Island Arts Center Barn on Route 2 hosts The Dixie Six: Satchmo's Louisiana Favorites, 4 to 5:30 p.m., $25 advance or $30 at the door, with Grand Isle's own Tony Pietricola on clarinet.

St. Albans has two things going at once on Church Street from 9 to 2: the Northwest Farmers Market in Taylor Park and the first annual Full Circle Market, a handmade-and-vintage market with a Repair Café run by the Northwest Solid Waste District. Both through Downtown St. Albans.

Killington runs Cooler in the Mountains at the K-1 Base Area, 3 to 5:45 p.m., with NYC jam band The Band Memo headlining and Nick & Rhys opening — free, with bar and BBQ on site. Details.

For history-minded folks, Kids Dig Mount Independence in Orwell puts children 6 to 12 into a simulated archaeological dig with real tools, 1 to 3 p.m. (Vermont Historic Sites). And out of Rockingham, guided Vermont Covered Bridge Tours depart the Kissing Bridge at the Vermont Country Store at 10, 12:30, and 3 — two hours, four bridges in Rockingham and Grafton, $30, thirteen seats per van. Book here.

Two small ones worth a mention because somebody should mention them: the Haskell Free Library in Derby Line has a free family music show with Shawny at 10:30 a.m., and the Alden Balch Memorial Library in Lunenburg throws its summer reading finale pizza party at 10:30 (town calendar). Middlebury closes the night with Reggae Night on the Town Hall Theater plaza at 6.

Sunday, August 9

Sunday's best free show is House of Hamill at Dog Mountain in St. Johnsbury, 5 p.m., part of the Levitt AMP series. Celtic-rooted fiddle and guitar, dog-friendly, food vendors on site, and a free shuttle from the St. Johnsbury Welcome Center at 4. Catamount Arts has the details. Dog Mountain on a summer evening with live fiddle is about as Vermont as the calendar gets.

Rokeby Museum in Ferrisburgh holds its annual Pie & Ice Cream Social, pie from 1 to 3 p.m., with the museum free all day 10 to 5 — homemade pie, Ben & Jerry's, live music, lawn games, and tours of the house and grounds. Via the Addison County Chamber.

The Champlain Islands have a good Sunday. Snow Farm Vineyard in South Hero runs a Summer Artisan Market from 11 to 4 with eight-plus local makers, overlapping an Estate Brandy Release Party from 1 to 4 — their first estate-grown grape brandy, and both events are free to attend. Meanwhile the North Hero Historic House Tour runs noon to 5, a self-paced driving tour with docents at each stop, benefiting the North Hero Volunteer Fire Department. Check in at Hero's Welcome.

The Mad River Valley does Summer Sundays on the Green at Joy Bar & Restaurant and the Mad River Shops green in Waitsfield, 11 to 5 — donation yoga at 11, lunch at noon, then live music from Madigan plus an artists market and kids' activities from 2 to 5 (listing). Then walk over to Lawson's Finest Taproom for Good Gravy at 3, free.

In Bellows Falls, Stage 33 Live hosts the Local Curator Series at 3 p.m. — Olivia Nied presenting Star Lane Sox and Scott Hsu. Forty seats, originals only, no covers. Weston has the RENT matinee at 2 with a post-show talkback.

Rutland County offers the East Hubbardton Cemetery Tour at the Hubbardton Battlefield, 2 to 4 p.m., where the Hubbardton Historical Society walks you through the East Hubbardton Cemetery and the settlers who fought in 1777 (details). Down at Chimney Point in Addison, Blast from the Past brings Green Mountain Timekeepers Society members out from noon to 4 with their clocks and watches, repair demos, and the story of the Barnes family clockmakers.

Up in the Kingdom, pianist David Feurzeig's Play Every Town project stops at the Plymouth Congregational Church in East Charleston at 2 p.m. — free, with donations going to the Echo Lake Protective Association. The Derby Historical Society hosts Christie Aldrich on NEK educator and explorer Flora Coutts, also at 2. Both via the Barton Chronicle.

Closer to home for Chittenden County folks avoiding the city: Shelburne Farms runs a guided Summer Forest Bathing walk from 9 to noon, $35 with registration required, and the Champlain Valley Expo in Essex Junction has Mt. Sinai Shriners Bingo at the Blue Ribbon Pavilion starting 10:30 a.m. (details). And the Stowe Farmers' Market runs 10 to 2 on the Mountain Road.

If the weather turns, Catamount Arts has CatVideoFest 2026 all weekend — Friday at 6, Saturday at 3 and 6, Sunday at 1. Yes, it is exactly what it sounds like, and yes, it sells out.

August in Vermont is short and it does not wait for you. Pick two, get in the car, and leave the phone in the glovebox.