Late August in Vermont is when the state squeezes every last drop out of summer, and this weekend the calendar shows it. The Vermont State Fair is in full swing in Rutland, Vergennes throws its biggest party of the year, and there's free music on a mountain covered in dog art. Here's where to point the truck.

Friday, August 21

Vergennes gets a head start on its big day with the Eve of Vergennes Day Street Dance at City Park, kicking off at 7:00 pm. The Little City closes things down, turns the music up, and lets everybody warm up their legs for Saturday's main event. Details on the whole weekend are at Vergennes Downtown.

In St. Johnsbury, Catamount Arts screens Canoe Dig It? at 6:30 pm — a mockumentary about the very real sport of freestyle canoeing, which is best described as canoe dancing. Seventy-eight minutes of cutthroat perfectionists and backwoods naturals battling for the Top Paddler ribbon at a fictional Maine regional final. Tickets run $10–$12 at Catamount Arts, 115 Eastern Ave.

Woodstock's Music by the River series lands at East End Park from 5:00 to 8:30 pm with singer-songwriter Jay Nash. Bring a blanket, grab food on site, and watch the Ottauquechee roll by. Info at Woodstock VT.

At the Vermont State Fair in Rutland, Friday night belongs to the SOS Promotions flat track motorcycle races at the grandstand — dirt, noise, and horsepower, the way a fair week should wind up. Schedule and tickets through the Paramount Theatre, which runs the fair's box office.

The Mad River Valley closes the day with The Anderson Trio's Night in New Orleans at 8:00 pm — an evening of hot jazz from the Anderson brothers. Details via the Mad River Valley Chamber.

And up on the border, the Haskell Opera House in Derby Line screens Dreamers & Steamers, a film by Louise Abbott, at 6:00 pm — in the opera house that famously straddles the international line. Details at Discover Newport.

Saturday, August 22

The big one: Vergennes Day, the 44th annual, runs 10:00 am to 3:00 pm at City Park. Pancake breakfast at the fire station, the Little City Road Races (1K kids' fun run up through a 15K), more than 55 crafters and vendors, live music on the bandstand, horse-and-wagon rides, and the Lions Club chicken BBQ. It's the Little City's whole personality packed into one Saturday. Full rundown at Vergennes Downtown.

In Rutland, the Vermont State Fair caps its week with Aaron Lewis and the Stateliners at the Diamonds and More Grandstand, 175 South Main St. Gates at 5:30 pm, show at 7:00. The Staind frontman turned country hitmaker — and a Vermont native, no less — brings the 2026 American Tour to the fairgrounds. Tickets from $55 through the Paramount Theatre.

Ludlow hosts the 6th Annual Best of Vermont Summer Festival at Okemo Field, 11:00 am to 5:00 pm Saturday and Sunday both. Craft beverage makers, cheese and maple producers, artisans, fine art, live music across folk, rock, and Americana, and a kids zone — a two-day showcase of Vermont-made everything. Details from the Okemo Valley Regional Chamber.

Montpelier turns Montpelier High School into a world stage for the World Soccer Festival, 9:00 am to 2:00 pm. The 14th annual edition features 3v3 youth games with each team repping a nation of its choice, a parade of flags, international food vendors, live music from Shidaa Project and Sambatucada, and an adult exhibition match pitting Capital Soccer against the Central America Stars. Free and family-focused — details at Montpelier Alive.

It's also peak farmers market season, and Saturday delivers wherever you are: the Waitsfield Farmer's Market runs 9:00 am to 1:00 pm (Mad River Valley Chamber), the Champlain Islands Farmers' Market sets up at St. Joseph's Church in Grand Isle from 10:00 to 2:00 (market site), the Northwest Farmers Market fills Taylor Park in St. Albans 9:00 to 2:00 (Downtown Saint Albans), and Woodstock's Mt. Tom Farmer's Market goes 9:30 to 12:30 (Woodstock VT).

In the Northeast Kingdom's far corner, Holland Elementary School hosts an Indoor Yard Sale and Vendor Event from 9:00 am to 2:00 pm — an honest small-town treasure hunt, Orleans County style. Details at Discover Newport.

Warren's Phantom Theater makes it a family double feature: a free-spirited Magic Show Workshop for Kids at 3:00 pm, then Ben Pratt, Magician takes the stage at 7:00 pm. Both via the Mad River Valley Chamber.

Catamount Arts runs its second Canoe Dig It? screening at 1:30 pm — this one with a Q&A; with filmmaker Samuel Dunning afterward, if Friday's show left you with burning freestyle-canoeing questions. Tickets at Catamount Arts.

And in Brattleboro, singer-songwriter Olivia Ellen Lloyd plays the Stone Church at 8:00 pm — West Virginia-born country-folk in one of the best-sounding rooms in southern Vermont. Details at The Stone Church.

Sunday, August 23

Sunday's headliner costs nothing: LADAMA at Dog Mountain, 5:00 pm, 143 Parks Rd. in St. Johnsbury, part of the Levitt AMP St. Johnsbury Music Series. The Latin alternative quartet — musicians from Brazil, Colombia, and Venezuela — earned NPR's praise for "irresistible spirit and universal appeal." Lawn chairs, picnics, and dogs all welcome; leave the outside booze home and hit the St. Johnsbury Distillery beer garden instead. A free shuttle runs from the Fairbanks Scales lot and the downtown Welcome Center starting at 4:00. Details at Catamount Arts.

In Stowe, bluegrass royalty comes to the Trapp Family Lodge Concert Meadow: the Dan Tyminski Band, doors at 5:00 pm, show at 7:00. The voice of "Man of Constant Sorrow" and longtime Alison Krauss collaborator — who happens to be a Rutland County kid originally — under the mountains as the sun drops. Tickets $21–$58 through Spruce Peak Arts.

The 3rd Annual Mad River Valley Summer Carnival runs 11:00 am to 2:00 pm — games, food, and Valley community spirit for the whole family. Details via the Mad River Valley Chamber.

Down in North Bennington, Lake Paran hosts the Third Annual New Vermonters Welcome Picnic starting at 1:00 pm. Free food, lake swimming, and a proper welcome mat for anyone who's recently made Vermont home — whether from across the country or two towns over. Details at Vermont Begins Here.

And the Best of Vermont Summer Festival runs its second day in Ludlow, 11:00 am to 5:00 pm — same lineup of makers, music, and maple as Saturday, one last chance to catch it.

Eleven counties, one weekend, and not a single excuse to stay on the couch. Get out there.