Lucky Pickers

Round Lake, IL

$500-$5000

Travels up to 200 miles

Get a free quick quote
Promotional video thumbnail 1 for Lucky Pickers

Toy Horses

Promotional video thumbnail 2 for Lucky Pickers

21st of May

Promotional video thumbnail 3 for Lucky Pickers

Characters

Gallery photo 1 of Lucky Pickers
Gallery photo 2 of Lucky Pickers
Gallery photo 3 of Lucky Pickers
Gallery photo 4 of Lucky Pickers
Gallery photo 5 of Lucky Pickers
Gallery photo 6 of Lucky Pickers
Gallery photo 7 of Lucky Pickers
Gallery photo 8 of Lucky Pickers

Overview

Lucky Pickers is an acoustic folk duet from Northern Illinois composed of acclaimed singer/songwriters Despina Pafralides and Caleb Peters. When they are not touring with their full time bands, Miles Over Mountains & Fox Crossing Stringband, the two seasoned multi-instrumentalists team up for an upbeat mixture of Americana and bluegrass driven tunes, showcasing heartfelt harmonies, skillful instrumentation and a passion for live performance. Their song selection runs deep ranging from old traditional music, all the way to more modern hit songs and everything in between, served up their own style. You can catch Lucky Pickers playing year round all over the Midwest & beyond.


Reviews

Be the first to review Lucky Pickers

Write a review

Booking information

Price range: $500-$5000

Languages: English

Gig length: 40 - 200 minutes

What to expect

While mostly performing as a folk duet with guitar/mandolin/fiddle/vocals, Lucky Pickers has recently started to expand into a larger group featuring some of the finest players in the Chicagoland area including upright bass, dobro, banjo and more. They can provide a nice easy going vibe with chill folk music, a more upbeat selection of popular cover tunes, or a freight train of barn burnin' bluegrass. Whatever the occasion, they aim to please the crowd and leave them with a great experience to remember.

About

Bio:
Lucky Pickers is an acoustic duet from Northern Illinois composed of acclaimed singer/songwriters Despina Pafralides and Caleb Peters. When they are not touring with their full time bands, Miles Over Mountains & Fox Crossing Stringband, the two seasoned multi-instrumentalists team up for an upbeat mixture of Americana and bluegrass driven tunes, showcasing heartfelt harmonies, skillful instrumentation and a passion for live performance. Their song selection runs deep ranging from old traditional music, all the way to more modern hit songs and everything in between, served up their own style. You can catch Lucky Pickers playing year round all over the Midwest & beyond.

While mostly performing as a duet, Lucky Pickers has recently started to expand into a larger group featuring some of the finest players in the Chicagoland area including upright bass, dobro, banjo and more. They can provide a nice easy going vibe with chill folk music, a more upbeat selection of popular cover tunes, or a freight train of barn burnin' bluegrass. Whatever the occasion, they aim to please the crowd and leave them with a great experience to remember.

See their full-time bands here:

(link hidden)

(link hidden)

Additional booking notes

We can provide a full professional sound system suitable for any kind of event from a small crowd of 20 people all the way to 500 people. If requested and budget permits, we can out source sound and lighting equipment/technicians for bigger events.

Past booked events

May 2026

08

Friday

Retirement Community Event

11:00pm - 3:00am (Sat)

East Chicago, IN

Set list

ACROSS THE GREAT DIVIDE (KATE WOLF)
BIG RAILROAD BLUES (GRATEFUL DEAD)
HESITATION BLUES (TRADITIONAL)
GOTTA GET DRUNK (WILLIE NELSON)
LONG WAY HOME (TOM WAITS)
ROSALIE MCFALL (GRATEFUL DEAD)
THE FOX (NICKEL CREEK)
HOBO SONG (GRATEFUL DEAD)
RAINS EVERYWHERE I GO (LYNN MORRIS)
EDEN (AMANDA ANNE PLATTE)
IF WISHES WERE HORSES (CLAIRE LYNCH)
DONT GIVE YOUR HEART TO A RAMBLER (TONY RICE)
MISS OHIO (GILIAN WELCH)
WHEN YA GET TO ASHEVILLE (STEVE MARTIN)
YOU AINT WOMAN ENOUGH (LORETTA LYNN)
GENTLE ON MY MIND (JOHN HARTFORD)
HEAVEN SENT (STEELDRIVERS)
MUDDY WATERS (IM WITH HER)
TALL BUILDINGS (JOHN HARTFORD)
LIVE FOREVER (BILLY JOE SHAVER)
OLD TIES & COMPANIONS (WATCHHOUSE)
GET NO BETTER ( JOHN HARTFORD)
HANGIN UP MY HEART (EMMY LOU HARRIS)
WILDFOWERS (PETTY)
HIGHWAY 40 BLUES (RICKY SKAGGS)
DRY TOWN (GILIAN WELCH)
BIG YELLOW TAXI (JONI MITCHELL)
ON AND ON (BILL MONROE)
LONG RIDE HOME (PATTY GRIFFIN)
WAYFARING STRANGER (TRADITIONAL)
CALL ME THE BREEZE (JJ CALE)
WALKIN DOWN THE LINE (BOB DYLAN)
BIG SPIKE HAMMER (BOBBY OSBORNE)
OLD HOME PLACE (JD CROWE)
BLACK EYED SUZY (JUSTIN TOWNES)
TOOK ALL THE RAMBLIN (BOXCARS)
HARD TRAVELING (WATCHHOUSE)
ROLL ON BUDDY (BILL MONROE)
DARK HOLLOW (DEAD)
MISS THEM TOO (AARON KELLY)
WHITE FREIGHTLINER BLUES (TOWNES VAN ZANDT)
NEVER MEANT TO LOVE YOU (CHISEL)
GHOST OF VIRGINIA (JUSTIN TOWNES)
NELLIE KANE (TIM OBRIEN)
21ST OF MAY (NICKEL CREEK)
I DONT KNOW (JUSTIN TOWNES)
TROUBLE IN MIND (TRADITIONAL)
ILL BE HERE IN THE MORNING (TOWNES VAN ZANDT)
LAST TRAIN FROM POOR VALLEY (NORMAN BLAKE)
IF I HAD A BOAT (LYLE LOVET)
WAYSIDE BACK IN TIME (PUNCH BROS)
FEATHERED INDIANS (CHILDERS)
ITS ALRIGHT (CHICAGO FARMER)
MIDNIGHT HIGHWAY (ROWAN)
DONT THINK TWICE (DYLAN)
IM SATISFIED (SWEET SUNNY SOUTH)
TONIGHT ILL BE STAYING (DYLAN)
SOUVENIRS (JOHN PRINE)
FISH & BIRD (TOM WAITS)
QUIT WHILE IM AHEAD (TURNPIKE TROUBADOURS)

Influences and inspiration

The band draws inspiration all over the board, while covering acts new and old. We have a good deal of traditional bluegrass tunes/fiddle tunes in our repitoire, as well as original material. Here are some artists you can expect to hear at a Lucky Pickers show:

Watchouse, Gilian Welch, Tom Petty, Willie Nelson, Dolly Parton, Bob Dylan, George Jones, Loretta Lynn, Glen Campbell, John Hartford, Sierra Ferrel, Paul Simon, Tyler Childers, Darrell Scott, Peter Rowan, Joh Prine, Grateful Dead, Justin Townes Earle, Chris Stapleton, The Byrds, Tom Waits & more...

Setup requirements

Power

Stage (or space) must be large enough to set up equipment

Check out these featured profiles

Ken Slauf

4.97 (27)
Top Performer
84 Verified bookings

  • Glen Ellyn, IL
  • Singing Guitarist
  • $200 and up

Courtney B. said “Ken was very engaging, funny, and a very talented performer. I highly recommend Ken for any performance. ”
Featured

Jonathan Moody

5.0 (76)
Top Performer
52 Verified bookings

  • Denver, CO
  • Singing Guitarist
  • $2,500 and up

Tiffany K. B. said “Jonathan was amazing. He is super talented- knows 500 plus songs of many genres. He has the best personality and delivers his music in a fun, entertaining, and personal way. His vocals are top tier! ”

The Westerlees

5.0 (1)
1 Verified booking

  • Antioch, IL
  • Swing Band
  • $600-2000

Jamie S. said “Band was very friendly and their music was enjoyed by all. Would recommend them for sure. ”
Featured

Guy Meets Girl

4.98 (38)
Top Performer
70 Verified bookings

  • Portland, ME
  • Acoustic Band
  • $350 and up

Robert M. M. said “Very responsive, excellent talent, prompt, respectful, everything we could have ever asked for! ”