The Byrd Pressley Band and comic Drew Fraser at Cove Haven Resort, 8:30pm.
Winter concert at Pond Eddy Methodist Church, Berm-Church Road, 2pm. Several choirs, barbershop and piano. Refreshments severed.
WJFF 90.5 FM presents a community Messiah sing-along at St. John's Episcopal Church, 15 St. John's St., 2pm. Admission: one or more non-perishable food items for the Caring Hands Food Pantry. 845/482-4141.
Friends of Max Siegel Benefit Showcase: Great Artists and Cause at Cracolici's on the Green, 2514 Route 52, 11:30am.
Mountain Wave at Sidetracks, 8:30pm.
Two jazz shows at Catskill Art Society. Jazz for Young Folks at 4pm, fun holiday music and jazz. Thurman Baker and Trinity at 7:30pm, music by Irving Berlin, originals and classic seasonal favorites. Lonnie Gasparini on organ, Miles Barnett on saxophone and Thurman Barker on percussion. $10 tickets.
Winterfest Rockin’ Christmas with John Curtin at Glass—wine. bar. kitchen. at Ledges Hotel, 8-11 pm. Fun times and great seasonal music. No cover charge. firstname.lastname@example.org or 570/226-1337.
The Monticello High School Music Department will hold their annual Winter Concert at the Arnold Packer Hughs Auditorium (High School), 7:30pm. The concert band, string orchestra and choral programs will perform selections from the repertoire. As a final number, members of the audience are invited to join the chorus. Free and open to public.
Big Band Concert with the Dan Bradley Big Band and meet-the-musicians reception at the Deerpark Reformed Church, 30 East Main St., 7pm. Snow date Sunday, Dec. 13 at 3pm. Tickets: $15 at the door; $10 in advance; students are free. Sponsored by Port Jervis Council for the Arts.
Tri-Valley student winter concert in the Tri-Valley Bernstein Theater, 34 Moore Hill Road, 7pm. Featuring performances by students in grades 5-8. Free admission.