Music for the Week: Applefest and more fun across the region

| 28 Sep 2026 | 11:13

Saturday, Oct. 3

At 1 p.m., Sean O’Flynn brings his solo acoustic set to Applewood Winery, 82 Four Corners Road.

Pennings Farm Cidery, 4 Warwick Turnpike, welcomes the Missyping Band to the stage at 3 p.m. with a $5 cover charge.

Back at Applewood Winery, Matt & Mere perform a duo set at 4:30 p.m.

Close the night out with High Noon, who bring country favorites to the Captain’s Table, 547 NY-17M.

Sunday, Oct. 4

Warwick’s most popular event, Applefest, begins at 9 a.m. across Main Street. Enjoy more than 150 craft vendors, 75+ food vendors, and apple pie baking and eating contests. Live music starts at 11 a.m. on four stages (2nd Street, Chase Stage, Railroad Green, and Stanley Deming Park), featuring NY-based artists like Americana artist Chris Reali and singer-songwriter Catch Me If You Can.

The Cove Castle Restaurant, 13 Castle Court, welcomes the Carolyn Weller duo to its lakeside stage at 1:30 p.m.

At 2 p.m., The Kootz Band brings its classic rock favorites to Clearview Vineyard, 35 Clearview Lane; JustUs performs at Applewood Winery; Ronnie Ebert brings his acoustic and electric rock songs to Silvio’s Italian Villa & Martini Bar, 274 NY-94; and Vera & The Force take the stage at the Warwick Valley Winery, Distillery & Orchard, 114 Little York Rd.

At 3 p.m., OC5 performs at Pennings Farm Cidery with a $5 cover charge, while Nick Pfeister leads an Oktoberfest celebration at the Captain’s Table.

Friday, Oct. 9

All One One All Farm, 221 Craigville Road, welcomes the Missyping Band for an intimate set at 5 p.m.

Pennings Farm Market, 161 State Route 94 S., welcomes Pauly Di Dio for a 6 p.m. set.

Later, at 7 p.m., Owls + Lions return to the Cove Castle, and Garret Gardner brings his multi-instrumentalist chops to Meadow Blues Coffee, 8 Greycourt Ave.