Eilen would often travel to old-time music jams near Boston. There she was introduced to like-minded traditional musicians and music lovers including her current drummer Jason Beek. Seeing that Boston had a lot to offer musically, Eilen moved there in late fall of 2003 and was quickly welcomed into the famous and vibrant folk and roots community. Over the next two years she performed solo and with alternating personnel, cutting her teeth at venues like Club Passim, Plough & Stars and Johnny D’s.
In early, 2005 Eilen began a successful Saturday evening residency at Tír na nÓg pub in Somerville, Massachusetts, which lasted until 2007. Week after week at the nÓg, Eilen solidified her band sound and strengthened her standing as a rising star in the Boston Americana and Folk scene.
In December, 2005, with a tight band including Beek on percussion, Daniel Kellar on violin, Jerry Miller on guitars and upright bass player Johnny Sciascia, Eilen entered Chris Rival’s renovated 19th-century barn/studio to record Boundary County. That album — until now the best representation of Eilen Jewell’s music — received swift and overwhelmingly positive attention from clubs, radio programmers and the press.
Summer 2007 brought Jewell’s first national release, Letters From Sinners & Strangers, recorded at the Signature Sounds studio in Pomfret, Connecticut. The album reached the Top 10 on the Americana weekly radio chart in addition to being listed on many critics' "best of" lists for 2007. LFS&S continues to receive critical acclaim from around the world.
Eilen and her band continue to tour nationally behind the album making stops at NPR's World Cafe, XM Radio, Mountain Stage, Woodsong's Old-Time Radio Hour, Falcon Ridge Folk Festival, Grassroots and many more radio stations, clubs and festivals.
2007 also found Eilen sharing the stage with a who's who list of Americana, Folk and Roots musicians. Among the highlights were Loretta Lynn, Chuck Prophet, Chris Smither, Fred Eaglemsith, Jimmy LaFave, Steve Forbert, Holly Golightly, Junior Brown, The Hacienda Brothers, Kris Delmhorst, The Holmes Brothers, Tom Russell and Jack Williams.