WannaGoSee — Live Music in New England

new england's live music guide

WEEK OF MAY 18 - MAY 24, 2026

From John & Jen at Colonial Theatre (Pittsfield) to Jerry Garcia Symphonic Celebration with the Boston Pops at Tanglewood and David Katzenstein & David Ricci Two Photographers in conversation at Mass MoCA.

TUESDAY - 5/19

Colonial Theatre (Pittsfield), Pittsfield — John & Jen at 7:00pm let's go
Tanglewood, Lenox — Jerry Garcia Symphonic Celebration with the Boston Pops at 19:00 feel the vibe

WEDNESDAY - 5/20

Colonial Theatre (Pittsfield), Pittsfield

THURSDAY - 5/21

Colonial Theatre (Pittsfield), Pittsfield
Mass MoCA, North Adams
  • 5:00pm — David Katzenstein & David Ricci Two Photographers in conversation art talk
  • 6:00pm — The Chalet chalet vibes

FRIDAY - 5/22

Colonial Theatre (Pittsfield), Pittsfield
Mahaiwe Performing Arts Center, Great Barrington
Mass MoCA, North Adams
  • - name: Wilco's Solid Sound 2026 – SOLD OUT — TBA rock out
  • 4:00pm — To Hell with Poverty! A Class Act: Inside the Gang of Four Jon King talk it out
Tanglewood, Lenox
  • - name: The B’s Passport to Summer — TBA summer vibes
  • 19:00 — Jazz at Lincoln Center Orchestra with Wynton Marsalis jazz vibes

SATURDAY - 5/23

Colonial Theatre (Pittsfield), Pittsfield
  • 2:00pm, 7:00pm — John & Jen let's go
  • 2:00pm, 7:00pm — John & Jen let's go
  • 7:00pm — An Enchanted Evening Celebrating Magic Tree House get enchanted
  • 7:30pm — Yacht Lobsters get funky
Mahaiwe Performing Arts Center, Great Barrington — BEATrio: Béla Fleck, Edmar Castañeda & Antonio Sánchez at 8:00pm discover beats
Mass MoCA, North Adams
  • - name: Taryn Simon The Pipes — TBA explore art
  • - name: Wilco's Solid Sound 2026 – SOLD OUT — TBA rock out
  • 10:00am — Community Free Day June 2026 free entry
  • 11:00am — Nehprii Amenii: HUMAN get inspired
  • 2:00pm — Pep Rally for the Trees Amanda Lovelee: Homecoming rally for trees
  • 3:00pm — Arielle Twist: Chopped chop it up
  • 4:00pm — American Rambler: Walking the Trail of Johnny Appleseed Isaac Fitzgerald in Conversation with Amanda Lovelee join the talk
  • 5:00pm — Head of Household Oliver Munday household chat
Tanglewood, Lenox

SUNDAY - 5/24

Colonial Theatre (Pittsfield), Pittsfield
Mahaiwe Performing Arts Center, Great Barrington — Close Encounters With Music: Romance of the Romani! at 4:00pm feel the rhythm
Mass MoCA, North Adams — TBA at - name: Wilco's Solid Sound 2026 – SOLD OUT rock out
Tanglewood, Lenox
  • - name: Berkshire Choral International: Celebrating African-American Composers — TBA choral vibes
  • 14:30 — Yacht Rock Revue – PRIMETIME Presented by CANN get groovy
  • 18:00 — Paul Simon rock out

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