Upcoming Events

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  Fri, Nov 13

  Lucky Pickers @ Main Street Outfitters, Wauconda, Illinois / 

  Main Street Outfitter

  Learn more

  Nov 13, 2026, 8:00 PM – Nov 14, 2026, 12:00 AM

  Main Street Outfitter, 513 S Main St, Wauconda, IL 60084, USA

  Join us at one of our favorite spots for live music! Free show - 8-11pm
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  Sat, Nov 14

  Lucky Pickers Trio @ Skeleton Key Brewing / 

  Skeleton Key Brewery

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  Nov 14, 2026, 7:30 PM – 10:30 PM

  Skeleton Key Brewery, 8102 Lemont Rd #300, Woodridge, IL 60517, USA

  Free show at Skeleton Key Brewing! Great Beer, good vibes! Free Show 7:30-10:30pm
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  Tue, Nov 17

  Lucky Pickers & Soggy Prarie @ Madison Bluegrass Roundabout #25 / 

  Harmony Bar & Grill

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  Nov 17, 2026, 6:30 PM – 10:10 PM

  Harmony Bar & Grill, 2201 Atwood Ave, Madison, WI 53704, USA

  Bluegrass Tuesday in Madtown!
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  Sat, Nov 21

  Despina Solo/Acoustic @ Pier 91 / 

  The Grill at Pier 91

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  Nov 21, 2026, 1:00 PM – 4:00 PM

  The Grill at Pier 91, 99 Kazimour Dr, Port Barrington, IL 60010, USA

  Saturday lunch and live music!
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  Sun, Nov 08

  Lucky Pickers Full Band @ Jennings Holler / 

  Jennings Holler

  Details

  Nov 08, 2026, 2:00 PM – 5:00 PM

  Jennings Holler, W379 S9674, County Rd S, Eagle, WI 53119, USA

  Its Bluegrass Stew at Jennings Holler! Eagle , WI Free show 2-5 pm Food Truck, Pizza, and drinks for purchase, no carry-ins.
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  Thu, Nov 05

  Lucky Pickers Duet @ Lindy's / 

  Lindy's Landing

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  Nov 05, 2026, 6:00 PM – 9:00 PM

  Lindy's Landing, 115 Park St, Wauconda, IL 60084, USA

  Join us at Lindy's Landing in Wauconda, IL for dinner & tunes! Thursday November 5th 6-9pm. 115 Park St, Wauconda, IL 60084
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  Sun, Oct 25

  Lucky Pickers @ 9th Street Pub / 

  9th Street Pub

  Details

  Oct 25, 2026, 5:00 PM – 8:00 PM

  9th Street Pub, 253 9th St, La Salle, IL 61301, USA
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  Fri, Oct 16

  Lucky Pickers @ Blind Corner Brewing / 

  Blind Corner Brewery

  Details

  Oct 16, 2026, 6:00 PM – 10:00 PM

  Blind Corner Brewery, 1665 Quincy Ave #155, Naperville, IL 60540, USA
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  Wed, Oct 14

  Lucky Pickers @ House Of Bogini / 

  House of Bogini

  Details

  Oct 14, 2026, 6:00 PM – 10:00 PM

  House of Bogini, 152 Center St, Lake Geneva, WI 53147, USA
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  Sun, Oct 11

  Lucky Pickers @ Science Project Brewing / 

  Science Project Brewing Company & Pizza

  Details

  Oct 11, 2026, 2:00 PM – 6:00 PM

  Science Project Brewing Company & Pizza , 611 North St, Logansport, IN 46947, USA
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  Fri, Oct 02

  Lucky Pickers @ Mackey's Hideout / 

  Mackey's Hideout

  Details

  Oct 02, 2026, 9:00 PM – Oct 03, 2026, 1:00 AM

  Mackey's Hideout, 2601 S River Rd, McHenry, IL 60051, USA
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  Sat, Sep 26

  Picnic in The Barn / 

  Evergreen Farm

  Details

  Sep 26, 2026, 4:00 PM

  Evergreen Farm, 4N928 Brown Rd, St. Charles, IL 60175, USA
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  Sat, Sep 26

  Lucky Pickers @ Johnny Appleseed Festival / 

  Depot Park

  Details

  Sep 26, 2026, 12:00 PM – 1:30 PM

  Depot Park, Crystal Lake, IL 60014, USA
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  Tue, Sep 22

  Lucky Pickers @ Naper Settlement / 

  Naper Settlement

  Details

  Sep 22, 2026, 4:00 PM – 8:00 PM

  Naper Settlement, 523 S Webster St, Naperville, IL 60540, USA
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  Sat, Sep 19

  Lucky Pickers @ Fox River House / 

  Fox River House

  Details

  Sep 19, 2026, 7:30 PM – 10:00 PM

  Fox River House, 211 S Walnut St, Appleton, WI 54911, USA
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  Sat, Sep 19

  LuLucky Pickers Trio @ Wolf & Fox Winery / 

  Wolf and Fox Winery

  Details

  Sep 19, 2026, 3:00 PM – 5:30 PM

  Wolf and Fox Winery, W1139 Lime Kiln Rd, New Holstein, WI 53061, USA
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  Fri, Sep 18

  Lucky Pickers Trio @ Budahn's Bar / 

  Budahns Bar

  Details

  Sep 18, 2026, 5:00 PM – 9:00 PM

  Budahns Bar, 121 S Main St, Mayville, WI 53050, USA
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  Wed, Sep 09

  Lucky Pickers @ Boathouse / 

  The Boat House Bar & Grill

  Details

  Sep 09, 2026, 6:00 PM – 9:00 PM

  The Boat House Bar & Grill, N2062 S Lake Shore Dr, Lake Geneva, WI 53147, USA
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  Sat, Aug 22

  Lucky Pickers / 

  Grassway Organics

  Details

  Aug 22, 2026, 4:00 PM – 8:00 PM

  Grassway Organics, W2716 Friemoth Rd, East Troy, WI 53120, USA
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  Fri, Aug 14

  Lucky Pickers @ Destihl Brewing / 

  DESTIHL Brewery and Beer Hall

  Details

  Aug 14, 2026, 6:00 PM – 10:00 PM

  DESTIHL Brewery and Beer Hall, 1200 Greenbriar Dr, Normal, IL 61761, USA