| Artist | Title | Album (* = New Release) |
|---|
| Opening set | | |
| Bruce Cockburn | The Coldest Night of the Year | Singles, 1979-2002 |
| Lynn Miles | The Coldest Winter in the History of the World | Winter* |
| Lynn Miles | This Heart That Lives in Winter | Winter* |
| Leonard Cohen | Winter Lady | Leonard Cohen |
| Ian Tamblyn | Northern Town | Superior: Spirit and Light |
| Set # 2 | | |
| Birds of Chicago | Dim Star of the Palisades | Real Midnight* |
| Redbird | Hold On | Redbird |
| Pesky J Nixon | Americans in Corduroys | Red Ducks V.2* |
| The Paul McKenna Band | Long Days | Paths That Wind* |
| Set # 3 | | |
| Tim Buckley | Valentine Melody | Tim Buckley |
| Danko/Fjeld/Andersen | Come Running Like A Friend | Ridin' On The Blinds |
| Set # 4 | | |
| Natalia Zukerman | Gas Station Roses | Gas Station Roses |
| Honor Finnegan | I Should Stop Having Sex With You | Roses and Victory* |
| John Wesley Harding | Love's Reign Of Terror | Swings and Roundabouts |
| Richard Thompson | I Feel So Good | Live at Crawley |
| Richard Thompson | Tear Stained Letter | Live UK '98 |
| Teddy Thompson | I Wish It Were Over | Separate Ways |
| Josh Ritter | New Lover | The Beast In Its Tracks |
| Set # 5 | | |
| Toby Walker | Whipping Post | Speechless |
| Michael Jerome Browne | My Road Is Rough and Ready | Sliding Delta* |
| Rj Cowdery | Across The Great Divide | Something Fine* |
| The Pines | Sleepy Hollow | Above The Prairie* |
| Set # 6 | | |
| Sofia Talvik | Give Me A Home | Big Sky Country* |
| Sofia Talvik | Big Sky Country | Big Sky Country* |
| Travis | Sing | The Invisible Band |
| The Infamous Stringdusters w/Sarah Jarosz | Won't Be Long | Ladies & Gentlemen* |
| Steep Canyon Rangers | Looking Glass | Radio* |
| Scott Wolfson & Other Heroes | And The Band Played On | Welcoming The Flood* |
| Set # 7 - remembering Bob Elliott and Dan Hicks | | |
| Bob and Ray | The Great Lakes Paperclip Company | Best of |
| Dan Hicks and His Hot Licks | Where's The Money? | Where's The Money? |
| Dan Hicks and His Hot Licks | Bad Grammar Baby | Original Recordings |
| Set # 8 | | |
| Tom Waits | Blue Valentine | Blue Valentine |
| Rufus Wainwright | My Funny Valentine | Sweetheart |
| Kate & Anna McGarrigle | St. Valentine's Day 1978 | Love Over and Over |
| Dylan | | |
| Bob Dylan | Love Sick | Live - Grammy Awards 2-25-98 |
Jim Faith, producer of the LI Winterfest, visited with us to preview this year's event.
