Our Top Picks in Boston
Photo: ajay_suresh (CC BY 4.0)
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The shows and nights out we’d tell a friend about, picked from everything on the calendar. They carry an “Our pick” badge wherever they appear on the site.
Highlights
Our pick Comedy Main Stage Show: Nightmare on Hanover Street
Improv Asylum · 16+
Our pick Comedy Trae Crowder
The Wilbur
Our pick Live Music The Man In Black: A Tribute to Johnny Cash
The Wilbur
Halloween Drag Brunch with Mizery
Club Café · $25 plus $2.25 fee · 21+
Halloween at Pazza: Costume Party
Pazza on Porter · Free · 21+
Our pick Live Music Jesse Welles
Roadrunner
Our pick Halloween Big D And The Kids Table: A Nightmare Before Halloween
Paradise Rock Club
Coraline: The Drag Tribute
Club Café · $35 ($45 VIP) plus fees
PruBoo 2026
Prudential Center · Free
Our pick Comedy Nate Jackson: Big Dog
The Wilbur
Our pick Sports & Watch Parties Celtics vs. Knicks
TD Garden
Our pick Sports & Watch Parties Bruins vs. Sharks
TD Garden
Our pick Live Music Rod Wave
TD Garden
Our pick Live Music Brian Simpson
Scullers Jazz Club · All ages
Our pick Community Boy Band Brunch – Y2K Halloween
City Winery Boston
Our pick Live Music Noah Gundersen: Rites of Spring US TOUR FALL 2026
City Winery Boston
Walter Street Burying Ground Tour
Walter Street Burying Ground · Free
Horse-of-Course: Meet the Park Ranger Horses
Arnold Arboretum, Hunnewell Visitor Center · Free
Every date
Friday October 23
Our pick Main Stage Show: Nightmare on Hanover Street
Improv Asylum · 16+
Our pick Coraline: The Drag Tribute
Club Café · $35 ($45 VIP) plus fees
Our pick Nate Jackson: Big Dog
The Wilbur
Our pick Celtics vs. Knicks
TD Garden
Our pick Brian Simpson
Scullers Jazz Club · All ages
Our pick Walter Street Burying Ground Tour
Walter Street Burying Ground · Free
Saturday October 24
Our pick Trae Crowder
The Wilbur
Our pick Halloween at Pazza: Costume Party
Pazza on Porter · Free · 21+
Our pick Jesse Welles
Roadrunner
Our pick Big D And The Kids Table: A Nightmare Before Halloween
Paradise Rock Club
Our pick Bruins vs. Sharks
TD Garden
Our pick Boy Band Brunch – Y2K Halloween
City Winery Boston
Our pick Horse-of-Course: Meet the Park Ranger Horses
Arnold Arboretum, Hunnewell Visitor Center · Free
Our pick Halloweentown Movie Night at Boston Landing
The TRACK at New Balance · Free · All ages
Sunday October 25
Our pick The Man In Black: A Tribute to Johnny Cash
The Wilbur
Our pick Halloween Drag Brunch with Mizery
Club Café · $25 plus $2.25 fee · 21+
Our pick PruBoo 2026
Prudential Center · Free
Our pick Rod Wave
TD Garden
Our pick Noah Gundersen: Rites of Spring US TOUR FALL 2026
City Winery Boston
Times, prices and age rules are checked against each venue or organizer’s own page; the check date is on every listing. Plans change, so confirm with the venue before you go.
For everything else, see this week, this weekend and just announced.
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