No More Sun brings alternative metal and rock to Rushing Duck Brewing in Chester on Oct. 11 at 5:30 p.m. (
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Saturday, Oct. 11
The day brings the return of the Sugar Loaf Fall Festival, a beloved Columbus Day/Indigenous Peoples’ Day weekend tradition that fills the charming hamlet of Sugar Loaf with artisan vendors, family-friendly activities, food trucks, and live music starting at 10 a.m.
Throughout the day, enjoy a variety of performances around the Hudson Valley. The Al’s bring their sound to Tin Barn Brewing at 1 p.m. (62 Kings Hwy Bypass, Chester), while Al Gross performs classic rock and pop favorites at Clearview Vineyard & Winery at 2 p.m. (35 Clearview Lane, Warwick).
Also at 2 p.m., Cat Bread takes the stage at Rushing Duck Brewing (2 Greycourt Ave., Chester), Soul Sense gets groovy at Warwick Valley Winery, Distillery & Orchard (114 Little York Road, Warwick), and Stereo Mikes (duo) plays at Applewood Winery (82 4 Corners Rd., Warwick). DJ Tina Marie of Whiskey Crossing spins at 3 p.m. at Pennings Farm Cidery (4 Warwick Turnpike, Warwick).
The evening heats up with the high-energy “Beatles vs. Stones: The Greatest Show That Never Was” at 5:30 p.m. at the Sugar Loaf Performing Arts Center (231 Creamery Pond Road, Sugar Loaf), while No More Sun brings alternative metal and rock to Rushing Duck Brewing, 2 Greycourt Ave., Chester, at the same time.
Georgia 5 delivers powerhouse hits at 6 p.m. back at Tin Barn Brewing, and the Jerry Vivino Quartet presents a smooth Jazz Dinner at 7 p.m. at The Cove Castle Restaurant (13 Castle Court, Greenwood Lake). Sinus Rhythm, a band of carrying the torch of Petty Young Dylans, takes over Mattingly’s Tavern (16 N. Main St., Florida) from 7–10 p.m. Jeremy Torres plays The Last Whisky Bar at 8 p.m. (45 Woodlands Way, Warwick), and Roxon closes out the night with rock tunes at 9 p.m. at The Captain’s Table (547 NY-17M, Monroe).
Sunday, Oct. 12
Sunday continues the Sugar Loaf Fall Festival at 10 a.m. with more artisan shopping, local flavors, and live music.
JP & Ed return to Applewood Winery at 1 p.m., while The Hip Replacements bring country, classic rock, and pop favorites to the Clearview Vineyard stage at 2 p.m.
Blue Arrow Farm (86 Glenwood Road, Pine Island) hosts its Grateful Oktoberfest starting at 2 p.m. with Felix and the Cats followed by Touch of Grey performing from 3–6 p.m. The event features festive food, beer, vendors, and family fun like face painting and bounce houses.
Also at 2 p.m., the Ladies of the 80s deliver nostalgic tunes at Warwick Valley Winery, Distillery & Orchard. At 3 p.m., Rich “The Bard” Northup plays at D’Boathaus (322 Lakeside Road, Hewitt), Carolyn Weller and Joe perform at The Last Whisky Bar, The Possums bring rock, country, and soul to Pennings Farm Cidery ($5 cover), and Lotion adds party rock vibes to Tin Barn Brewing.
Monday, Oct. 13
Monday offers a relaxing holiday soundtrack with live music across the region. At 2 p.m., Alex Mazur performs at Warwick Valley Winery, while Big Frank and Mike play at Applewood Winery. At 3 p.m., the Jackson and Johnson Trio perform at Pennings Farm Beer Garden (161 State Route 94 S., Warwick), closing out the long weekend with feel-good tunes and local brews.
Wednesday, Oct. 15
Danny C’s Cruise Night and Concert Series starts at 4 p.m., featuring High Strung revving up the crowd with rock favorites. At 6:30 p.m., Meadow Blues Coffee (8 Greycourt Ave., Chester) hosts the Tim & Matt Duo, Tim Haufe and Matt Raymond, blending guitar, upright bass, and harmonies to deliver a soulful journey through originals and the American songbook, touching on folk, jazz, and blues influences.
Thursday, Oct. 16
Felix and the Cats are back at Blue Arrow Farm for another lively night of rock and blue starting at 6 p.m. At 7 p.m., Trails End Taphouse at GWL Garden Market (1197 NY-17A, Greenwood Lake) hosts its weekly Open Mic Night, inviting musicians, poets, and comedians to share their talents in a warm community setting.
Meanwhile, at 7:30 p.m., Floyd Pink performs at City Winery Hudson Valley (23 Factory St., Montgomery), offering a note-perfect tribute to the legendary sounds of Pink Floyd with a full-band experience and immersive stage show.
Friday, Oct. 17
At 5 p.m., Missyping Band performs at All One One All (AOOA) Farm (221 Craigville Road, Goshen), while Time Peace Trio brings their groove to the Beer Garden at Pennings Farm. Strings Attached rocks Tin Barn Brewing at 6 p.m., and Myles Mancuso returns with his powerhouse performance at 7 p.m. at The Cove Castle Restaurant. Open Mic Night at Mattingly’s Tavern also begins at 7 p.m., hosted by Nicole Resty Phillips. Andrew Jordon performs an intimate set at 8 p.m. at The Last Whisky Bar, and Hudson Blue closes the night with a high-energy show at 8:30 p.m. at Barrel 28 (28 N. Main St., Florida).
Send upcoming music event information to Stefani at themicnj@gmail.com.