13 Things to Do in Boston This Week · October 15–18, 2026

Festivals & Special Events

Head of the Charles Regatta

Rowing teams from across the country compete on the Charles River while you take in the autumn scenery along the banks.

Friday, October 16 – Sunday, October 18, 2026 · Cambridge

Open Streets Roslindale

Major city streets go car-free for walking, biking, skating and rolling, with local vendors, live music and community activities.

Sunday, October 18, 2026 10:30 AM · Roslindale

Arts & Culture

Mortified Live

A live staging of the Mortified show presented by WBUR Events.

Friday, October 16, 2026

Improv With My Friends From Work – with Cast and Writers from SNL

An improv show featuring cast and writers from Saturday Night Live at The Wilbur.

Sunday, October 18, 2026 · The Wilbur

Operation Mincemeat: A New Musical

The Tony and Olivier Award-winning musical brings its Broadway and West End run to the Emerson Colonial Theatre.

Tuesday, October 13 – Sunday, October 25, 2026 · Emerson Colonial Theatre, Boston

Stories from the Stage: Close Encounters

An in-person night of live storytelling from GBH's Stories from the Stage, with storytellers sharing unexpected connections and encounters.

Thursday, October 29, 2026 6:30 PM · GBH Calderwood Studio

Family-Friendly

The Big Squash: An Annual Pumpkin Festival

The second annual pumpkin festival at First Street Market, billed as a family outing.

Saturday, October 17, 2026 · First Street Market, Cambridge

Doggone Halloween Pet Parade

Boston's beloved Halloween dog costume parade with a POOCHAPALOOZA zone, photo booth, face painting, free treats and prizes for best costumes and dog-and-owner duos.

Saturday, October 24, 2026 · Downtown Crossing

Stroller Walk + Pelvic Health Q&A with Pacer PT

A stroller walk through Seaport with coffee and a pelvic health Q&A with Pacer Physical Therapy for active moms.

Sunday, October 25, 2026 10:00 AM – 11:30 AM · Backyard Boston, 5 Necco Street, Seaport

Food & Drink

Curated Cuisine: Eric Ripert on Finding Joy & Connection Through Food

James Beard Award-winning chef Eric Ripert discusses finding joy and connection through food as part of WBUR's Curated Cuisine series.

Friday, October 23, 2026

Music & Nightlife

Con Brio Lunch Club: Kinti

Cellist Rebecca Hartka joins multi-instrumentalist Curi Inti Cachimuel Amaguaña for an afternoon of indigenous music as Kinti, with lunch included.

Friday, October 16, 2026 11:00 AM · All Newton Music School, 321 Chestnut Street, West Newton

The Music of Hey Arnold! Live!

A live concert of the music of Hey Arnold! featuring Jim Lang and The PS 118 AllStars with special guest Craig Bartlett.

Wednesday, October 28, 2026 · Chevalier Theatre

Date Night

Jim Gaffigan: Everything Is Wonderful Tour

Family-friendly stand-up from Jim Gaffigan on his Everything Is Wonderful Tour at the Wang Theater.

Friday, October 23 – Sunday, October 25, 2026 · Wang Theater