Skip to content
The Rose Kennedy Greenway and downtown Boston at dusk

Things to Do in Boston This Weekend

October 23–25, 2026

Updated Tuesday, October 20, 2026

Operation Mincemeat plays its last Boston shows this weekend, the Boston Symphony Orchestra premieres a piece written to play alongside a live AI system, and Downtown Crossing puts dogs in costume and free chowder on the same Saturday afternoon. Halloween is a week from Saturday, and plenty of the picks below are costume-friendly.

Here is what we would actually go to in Boston this weekend, sorted by day. Every pick has the time, the place, the price when the organizer lists one, and a link to the full event page.

Jump to: Friday · Saturday · Sunday · All weekend

Friday, October 23

James Beard Award-winning chef Eric Ripert is at WBUR CitySpace to talk about his new cookbook, Mindful Cooking, with Morning Edition host Tiziana Dearing. The book has more than 75 plant-based recipes shaped by his travels to Buddhist monasteries in Japan and Korea, and everyone gets a taste of the butternut squash-amole from the book after the talk. Brookline Booksmith is selling signed copies.

Doors 5:30 p.m., talk 6:30 p.m. · 890 Commonwealth Ave · General $20, students $10 with ID (premier seats are sold out)

Broken Records is throwing its first Pumpkinfest, with unlimited samples of fall beers and seasonal cocktails from local breweries and liquor brands. You vote for your favorite beer and cocktail while a DJ plays, and free karaoke takes over at 9 p.m.

7:00 p.m. · 85 Guest Street · $11.54 on Eventbrite, 21+ with ID, no refunds

Kent Nagano conducts the Boston Symphony Orchestra in the world premiere of Tod Machover’s already and not yet, a BSO commission that uses a live AI system working with each musician in the orchestra. Mendelssohn’s Hebrides Overture opens the program, his Reformation Symphony closes it, and the U.S. premiere of Alex Nante’s Ein feste Burg sits in between.

Friday 1:30 p.m. (pre-concert talk 12:15) or Saturday 8:00 p.m. · Symphony Hall · Tickets at bso.org

Bruce Cockburn has written more than 400 songs over a career of more than 50 years, picked up 13 JUNO Awards and landed in the Canadian Music Hall of Fame, and on Friday he brings that songbook to the Chevalier in Medford. Livingston Taylor opens, and this tour is the first time the two have shared a stage.

Doors 7:00 p.m., show 8:00 p.m. · 30 Forest Street, Medford

Saturday, October 24

The Downtown Boston Alliance’s dog costume parade fills Downtown Crossing with a Poochapalooza Zone, a photo booth, face painting and free treats. Dogs compete for Best Costume, Cutest Costume, Scariest Costume, Best Dog and Human Duo, and Best Dog and Child Duo, and you can register your dog on the Alliance’s page.

Noon to 3:00 p.m. · Summer Street Plaza and Washington Street

  • Chowderfest

    Sat, Oct 24 · 4:00–6:00 PM

    Summer Street Plaza · Boston

    Chowderfest

Stay downtown after the parade. Chowderfest follows it on the same block, and restaurants and chefs each serve their own take on New England chowder for two hours. It costs nothing to get in.

4:00 to 6:00 p.m. · 425–431 Washington Street · Free

Boston Landing is screening Halloweentown indoors at the TRACK at New Balance, and costumes are encouraged. The pre-party starts at 3:30 p.m. and the movie starts at 5:30. It is free, but you need to RSVP on Eventbrite, and seats are first come, first served.

Pre-party 3:30 p.m., movie 5:30 p.m. · 91 Guest Street · Free with RSVP

Big D and the Kids Table play their pre-Halloween show at the Paradise with The Pietasters and Devon Kay and the Solutions on the bill. Doors are at 6:30 p.m., the show starts at 7:30, and it is all ages.

Doors 6:30 p.m., show 7:30 p.m. · 967 Commonwealth Ave · All ages

  • Bloody Book Bash

    Sat, Oct 24 · 7:00–9:00 PM

    Porter Square Books: Boston Edition · Seaport

    Bloody Book Bash

Porter Square Books’ third Bloody Book Bash puts horror authors Gretchen Felker-Martin, Nicky Gonzalez, Eric LaRocca, Aaron Mahnke and Rebecca Mahoney at signing tables in its Seaport store. The night also has a costume contest, a screening of Creature From the Black Lagoon, trivia, food and drinks.

7:00 to 9:00 p.m. · GrubStreet, 50 Liberty Drive, Suite 500 · $5

Sunday, October 25

The Gardner’s annual chrysanthemum installation is up in the Courtyard, and this concert in Calderwood Hall is built around the flower. The program runs from Puccini’s Crisantemi and Scott Joplin’s The Chrysanthemum to Tōru Takemitsu, played by a group that includes strings, flute, piano, mezzo-soprano and accordion. Director of Horticulture Erika Rumbley and music curator George Steel host.

1:30 to 3:30 p.m. · Calderwood Hall, 25 Evans Way · Tickets online or 617-278-5156

The SoWa Vintage Market sets up downstairs at 450 Harrison Ave every Sunday, year round and rain or shine, with antiques, collectibles, vintage goods and one-of-a-kind curiosities. Pair it with the Gardner concert for a full Sunday.

Sunday · Downstairs at 450 Harrison Ave, South End

All weekend

This is your last chance to see the Olivier and Tony Award-winning musical in Boston. Operation Mincemeat tells the true World War II story of a stolen corpse, a fake love letter and Ian Fleming, and the Boston run ends Sunday before the tour moves on to Toronto.

Friday through Sunday · 106 Boylston Street · Last show Sunday 6:30 p.m.

The Boston Globe’s 12th GlobeDocs Film Festival spends its last in-cinema weekend at the Brattle, and every program comes with a filmmaker Q&A. Friday has Barbara Kopple’s Union Town at 6:00 p.m. and Jean-Michel Basquiat, a portrait led by the artist’s sisters, at 8:30.

Friday through Sunday · 40 Brattle Street, Cambridge · $17 per film, students $10 with a .edu email, all sales final

Jim Gaffigan brings his Everything is Wonderful! tour to the Wang Theatre for three nights: Friday at 7:30 p.m., Saturday at 8:00 and Sunday at 7:00. His special The Skinny was Hulu’s first original stand-up special.

Fri 7:30 p.m., Sat 8:00 p.m., Sun 7:00 p.m. · 270 Tremont Street · From $50.50 at the box office

The New England Aquarium hides “sunken” jack-o’-lanterns throughout its exhibits on Saturday and Sunday, and costumes are welcome. There is also a fall animal scavenger hunt, animal skulls and bones to see up close with Aquarium educators, and Halloween treats at the Harbor View Café.

Saturday and Sunday · 1 Central Wharf

Stone Zoo fills its grounds with hundreds of lit pumpkins and larger-than-life sculptures Thursday through Sunday nights until October 31. Every guest needs a ticket, zoo members included, and kids under 2 are free.

5:30 to 9:30 p.m., last entry 8:30 · 149 Pond Street, Stoneham · Prices vary by date

Get the weekend in your inbox

Our weekly events calendar goes out every Thursday to 45,000 subscribers. Sign up for the newsletter to get it before the weekend starts.

Browsing the events calendar and submitting an event are free for everyone. Members get free and discounted tickets, priority guest lists, unlimited searches on The Move and the ability to save events, all for $9.99 a month or $99 a year.

Boston this weekend, quick answers

What is free to do in Boston this weekend?

Chowderfest on Saturday from 4:00 to 6:00 p.m. at 425–431 Washington Street is free, and so is the Halloweentown screening at the TRACK at New Balance, as long as you RSVP. The Doggone Halloween parade in Downtown Crossing hands out free treats.

When does this page change?

Every Thursday, with picks for the coming Friday through Sunday. For everything else on in the city, browse the full events calendar.

Members

Unlock to use this feature!

Become a member

$9.99 a month or $99 a year. Cancel anytime.