The
AllMusic review by Sean Westergaard awarded the album 4 stars out of 5, stating "These guys are sonic explorers and over the course of the session they go just about everywhere: electronic ambient, soul jazz, rock freakouts, '50s sci-fi, mysterious exotica, and even a little taste of New Orleans. It's not for everyone, but fans of either band should be thrilled, as should anyone interested in well-done experimental music without boundaries". Writing for
All About Jazz, John Kelman said "
Woodstock Sessions, Vol. 2 finds the decade-long Wilco guitarist encouraging the trio to go to musical places no one has truly gone before. It may be a roller coaster of a listen but it's still somehow a strangely attractive one, especially when experienced old school, as a whole rather than a set of nine individual tracks".
PopMatters Will Layman stated "
Woodstock Sessions Vol. 2 features a group of musicians who could easily play to the audiences that are so utterly ready to love them. Instead, they play for themselves, for the passion they have for their art. It’s not a record to alienate fans, but it’s a record to challenge fans and win them over to stretches beyond their comfort zone. A thrill, a dare, a terrific record". ==Track listing==