MONADNOCK REGION, N.H. (MyKeeneNow) Labor Day weekend is here, and the calendar is packed with ways to savor summer’s final fling. Think art fairs under the trees, live music spilling into downtown streets, quirky theater, and a classic Vermont fairground full of fried dough and farm animals. Whether you’re chasing big sounds, small-town traditions, or just one more excuse to stay out late, there’s plenty to fill the long weekend.

Friday, Aug. 29

Freeway Clyde with Jentri Jollimore & Ollella
7 p.m. at Nova Arts, Brewbakers Café, 48 Emerald St., Keene
Freeway Clyde, led by Vermont composer Michael Chorney, blends folk roots with sweeping improvisation and electric soundscapes. Local songwriter Jentri Jollimore and indie-folk cellist Ollella join the bill. Doors open at 7 p.m., music begins at 7:30 p.m. Tickets include a “name your price” access option.
More information: novaarts.org

Sandglass Theater’s Legacy Series: Feral
7 p.m. at New England Youth Theatre, 100 Flat St., Brattleboro, VT
Sandglass Theater presents Feral, a dark, allegorical puppet performance exploring transformation and identity. The show includes a post-performance puppetry “taster” with the artists.
More information: sandglasstheater.org

Conor McPherson’s The Night Alive
7:30 p.m. at Actors Theatre Playhouse, Brook and Main streets, West Chesterfield
This dark Irish comedy follows a man down on his luck who seeks redemption. Tickets are $17. The show continues Saturday and Sunday, and again Sept. 4-6.
More information: atplayhouse.org

Christopher Durang’s Laughing Wild
7:30 p.m. at The Edge Ensemble Theatre, 310 Marlboro St., Keene
The Edge Ensemble opens its 35th season with Durang’s offbeat comedy featuring absurd encounters and sharp commentary on modern life. Tickets $18-$20, available at the door.
More information: edgeensemble.org

Magnolia Boulevard
8 p.m. at The Stone Church, 210 Main St., Brattleboro, VT
The Lexington, Ky., band brings its blend of Appalachian rock, soul, blues and jam-inspired energy to the Stone Church stage.
More information: stonechurchvt.com

Saturday, Aug. 30

Art in the Park
10 a.m. to 4 p.m. at Ashuelot River Park, West St., Keene
The Monadnock Area Artists Association hosts its 67th annual outdoor art show and sale, featuring more than 75 regional artists, live music and food vendors. Free admission. Event continues Sunday.
More information: monadnockareaartists.org

Keene Music Festival 2025
11 a.m. to 9:45 p.m. throughout downtown Keene
Seven stages with performances across genres fill Main Street and beyond for Keene’s largest free annual music event. All ages welcome.
More information: keenemusicfestival.org

Della Mae
7 p.m. at The Park Theatre, 19 Main St., Jaffrey
GRAMMY-nominated, all-female string band Della Mae performs a night of roots and Americana. Tickets $35 in advance, $40 day of show.
More information: dellamae.com

Sandglass Theater’s Legacy Series: Feral
7 p.m. at New England Youth Theatre, Brattleboro, VT
Second performance of the production that blends puppetry, live music and storytelling.
More information: sandglasstheater.org

Conor McPherson’s The Night Alive
7:30 p.m. at Actors Theatre Playhouse, West Chesterfield
Second weekend performance of the acclaimed Irish play.
More information: atplayhouse.org

Sunday, Aug. 31

Art in the Park
10 a.m. to 4 p.m. at Ashuelot River Park, Keene
Final day of the annual art fair with regional artists, raffles and live music.
More information: monadnockareaartists.org

Guilford Fair
9 a.m. to 5 p.m. at Guilford Fairgrounds, 163 Fairground Road, Guilford, VT
The fair features horse draws, livestock shows, shearing demos, a car show, rides, live music, games and local food. Admission $5-$10. Continues Monday.
More information: guilfordfairvt.com

Christopher Durang’s Laughing Wild
3 p.m. at The Edge Ensemble Theatre, Keene
Final weekend performance of Durang’s dark comedy.
More information: edgeensemble.org

Conor McPherson’s The Night Alive
2 p.m. at Actors Theatre Playhouse, West Chesterfield
Sunday matinee of the dark Irish comedy.
More information: atplayhouse.org

Monday, Sept. 1 (Labor Day)

Guilford Fair
9 a.m. to 5 p.m. at Guilford Fairgrounds, Guilford, VT
Final day of the Guilford Fair with exhibits, food and entertainment.
More information: guilfordfairvt.com

Hops for Vets Car Show
11 a.m. to 2 p.m. at Frogg Brewing, 580 Sawyers Crossing Road, Swanzey
Frogg Brewing hosts a Labor Day car show fundraiser for Newport Vets Post 25, with live music, food trucks and raffles.
More information: froggbrewing.com

Celtic & Québécois Festival – Bandwagon Summer Series
3 p.m. at Scott Farm Orchard, 707 Kipling Road, Dummerston, VT
Next Stage Arts presents a Labor Day concert with Cantrip, Keith Murphy & Yann Falquet, and Cécilia, celebrating Celtic and Québécois traditions.
More information: nextstagearts.org