Things to do in Boston this weekend, October 16 - 19th

October 16, 2025

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THURSDAY - OCTOBER 16th

Art-Making After Dark @ ICA @ 6PM Enjoy free admission, art-making activities designed by local artists, gallery tours, & more!

Jazz Urbane Cafe @ ICA @ 7:30PM Jazz Urbane Cafe returns to the ICA with a thrilling evening of music featuring some of Boston’s best and most beloved musicians.

Yung Lean @ House of Blues @ 7PM With The Taxidermists

Xana @ Paradise Rock Club @ 7PM With Siena Liggins

Watchhouse @ Royale @ 8PM With Frail Talk

FRIDAY - OCTOBER 17th

College Night @ ICA @ 6PM Head to the Seaport for a night of creative art-making, unbeatable music, and stunning harbor views.

The Jury Experience @ Calderwood Pavilion @ 6PM / 8:30PM Enjoy an immersive theatre courtroom drama where you make tough decisions, dissect evidence, and give the final verdict.

Ballet of Lights: Cinderella @ Huntington Theatre @ 6:30PM Talented performers in illuminated costumes from Ballet of Lights bring this classic story to life through dance, light, and color.

Candlelight: 90s Hip-Hop on Strings @ First Church Cambridge @ 8:45PM Your favorite throwback Hip-Hop hits reimagined in classical sound! Featuring selections by Wu Tang Clan, Outkast, 2Pac, Nas, & more.

Acceptance @ The Palladium @ 7:30PM With Just Surrender & Head North

SATURDAY - OCTOBER 18th

Spicetoberfest @ Cityhall @ 4 - 10PM 🎃 SpicetoberFest is a spicy harvest festival and Boston’s hottest fall celebration of bold local flavors and vibrant culture. The festival will celebrate Boston’s diverse culinary and cultural fabric by providing a platform for spicy food vendors, urban farmers, Chefs, local hot sauce makers, artisan and craft beverages, and entertainers to showcase their talent.

Boston Cider Fest @ Time Out Market @ 1PM Boston Cider Fest returns with another year of free samples, seasonal themed dishes, live dj sets, and more!

Small Mart: Halloween Edition @ Crystal Ballroom @ 11AM Expect a lineup of vendors bringing you the best in vintage, handmade, and artist-made goods leaning into the spooky, eerie, and seasonally inspired.

Driveways @ Paradise Rock Club @ 7PM With Winona Fighter & Keep Flying

Revocation @ Brighton Music Hall @ 6PM With Inferi, Vomit Forth, & Judiciary

Jeff Tweedy @ Royale @ 8PM With Macie Stewart

Bingo Loco @ The Palladium @ 6PM / 10PM After sold-out shows in 200 locations around the globe, Bingo Loco stops in Boston for a unique rave party complete with comedian MCs, throwback anthems, lip sync battles, and more!

SUNDAY - OCTOBER 19th

SomerStreets: Monster Mash @ Somerville Avenue @ 2PM SomerStreet is closing busy streets for a day of family fun complete with live music, dancing, vintage market, and a Halloween costume parade!

Black Owned Bos. Market @ Seaport @ 12PM From gifts and apparel to packaged foods and beauty & skincare products, the market features Black-owned businesses from the Greater Boston area.

Wicked Good Aht Mahket @ Arts at the Armory @ 12PM Fall is in the air, and the Aht Dept is bringing you a harvest of creativity! Celebrate with local makers, whimsical wonders, and treasures ripe for the picking.

Aly & AJ @ Roadrunner @ 7PM With Amanda Shires

Lao Lang @ Orpheum Theatre @ 8PM With Zhang Weiwei & Guo Long

Ruston Kelly @ The Sinclair @ 8PM With Sam MacPherson

Guerilla Toss @ Crystal Ballroom @ 8PM With Godcaster & Jonny Tex

ALL WEEKEND

SATURDAY & SUNDAY - AppleFest @ Wachusett Mountain This fall festival celebration includes over 100 craft exhibitors, a farmers' market, kids entertainment, and peak fall foliage viewing from the SkyRide.

SATURDAY & SUNDAY - Boo at the Zoo @ Stone Zoo @ 9AM This year’s Haunted Happenings include a trick-or-treat trail, costume contests, education stations, tasty treats, and more family-friendly activities.

All weekend - Head of the Charles Regatta Since 1965, rowers have come from near and far to take part in the world’s largest Regatta. Make sure to check out the best viewpoints in the city!

All weekend - Big Apple Circus @ Suffolk Downs Witness the comedic performances, jaw-dropping trapeze artistry, and high-energy acrobatics and human pyramids in this renowned circus show. Ends 11/2.

All weekend - Boston Palestine Film Festival @ Multiple Venues The Boston Palestine Film Festival presents compelling films with independent views of Palestine’s history, culture, and geographically dispersed society. Ends 10/26.

All weekend - Boston Asian American Film Festival
BAAFF empowers Asian American filmmakers and showcases Asian American experiences and perspectives through award-winning films. Ends 10/26.

All weekend - Haunted Histories: Condemned Performance @ Peabody Essex Museum Enjoy an exclusive immersive theater performance set in PEM’s haunted mansions and inspired by spooky historical events.

All weekend - Tchaikovsky’s Symphony No. 5 in Concert @ Symphony Hall The BSO performs Tchaikovsky’s Fifth Symphony with its passionate themes, rich orchestral colors, and triumphant finale.

All weekend - ‘Hamilton’ Musical @ Citizens Opera House Don’t miss the chance to see this epic saga about the life and legacy of Founding Father Alexander Hamilton and find out why it has made a profound impact on the way we think about our history. Ends 11/2.

All weekend - ‘SIX’ Musical @ Hanover Theatre From Tudor Queens to Pop Icons, the SIX wives of Henry VIII take the microphone to remix five hundred years of historical heartbreak into a celebration of 21st century girl power!

All weekend - ‘The Ballad of Little Jo’ Musical @ BCA Plaza Theatre Inspired by a true story and told through a folk-infused score, the musical explores identity, prejudice, fear, and the beauty and horror of the American West at the end of the 19th century. Ends 11/2.

All weekend - ‘300 Paintings’ Play @ Farkas Hall In his renowned solo performance, comedian Sam Kissajukian brings audiences on a hilarious and wildly original rollercoaster ride exploring the ties between art, mental health, and creativity. Ends 10/25.

All weekend - ‘Macbeth’ Play @ The Mosesian Center for the Arts Set against the backdrop of the Cold War, Actors’ Shakespeare Project present their own rendition of Shakespeare’s masterpiece of betrayal, control, and tyranny. Ends 10/26.

All weekend - ‘Sardines’ Play @ The Huntington Theatre This deliciously authentic, insightful, and laugh–out–loud show created and performed by actor-comedian Chris Grace explores answers to life’s most difficult questions. Ends 11/16.

All weekend - ‘The Cottage’ Play @ Company Theatre The true meaning of fate, identity and marriage are called into question as a surprising and hilarious web of secrets unravels in this ridiculous – potentially murderous – romantic comedy. Ends 10/26.

All weekend - ‘Our Town’ Play @ Lyric Stage Capturing the themes of love, community, and the passage of time, this beloved production explores everyday lives of residents in a fictional New Hampshire town in the early 20th century. Ends 10/19.

ONGOING

Ongoing - ‘Sinister Streets’ Walking Tour @ Peabody Essex Museum This indoor/outdoor walking tour takes visitors through the dark side of Salem history - highlighting landmarks from the 1600-1800s. Ends 11/23.

Ongoing - ThotBot Implantation Center @ Bow Market, Somerville Is your ThotBot Glitched? Find out at this immersive installation and multimedia concert based in a 1990s post-apocalyptic dystopian storyworld. Ends 3/28/26

Ongoing - New England Renaissance Festival @ King Richard’s Fairgrounds Saturdays & Sundays* - King Richard’s Faire is the premiere fall entertainment event for all things Renaissance. Ends 10/30.

Ongoing - Open Market @ SoWa @ 11AM Sundays* One of the largest open-air farmer and artist markets returns this summer season! Ends 10/26.

Ongoing - Artisan Market @ Rose Kennedy Greenway @ 11AM Saturdays* Run by Somerville Flea, this summertime market features talented area artists, crafters, and independent designers. Ends 10/25.

Ongoing - Downtown Boston Arts Market @ Summer Street Plaza Thursdays & Fridays* - Located in the heart of the city, the Arts Market features artisans, crafts people, and local creative talent selling their wares in Downtown Boston. Ends 10/24.

Ongoing - Farmers Market @ Copley Square Fridays* - The largest market in the city, Copley Square Farmers Market offers a cornucopia of local produce, meats, dairy, baked goods, and prepared meals, as well as some non-edible products. Ends 11/25.

Ongoing - Boston Lights: A Lantern Experience @ Franklin Park Zoo
Prepare to be dazzled by the magic of all-new lantern displays, immersive walkthroughs, enchanting interactive displays and Instagrammable moments at every turn. Ends 11/2.

Ongoing - ‘Monsters of the Deep: Between Imagination and Science’ Exhibition @ MIT Museum Using historical prints, this exhibit traces the scientific process of observing, measuring, and describing that turned whales from monsters into mammals. Ends 1/2026.

Ongoing - ‘The Visionary Art of Minnie Evans’ Exhibition @ MFA Experience Minnie Evans’ imaginative and intricately detailed drawings inspired by the artist’s religious beliefs, interest in mythology and history, and the landscapes in her native North Carolina. Ends 10/26.

Ongoing - ‘Rachel Ruysch: Artist, Naturalist, and Pioneer’ Exhibition @ MFA This exhibition brings together 35 of the finest works by pioneering Dutch artist Rachel Ruysch, whose still life paintings invite viewers to reflect on the beauty of the natural world and women’s role in 18th century Netherlands. Ends 12/7.

Ongoing - ‘Deep Waters: Four Artists and the Sea’ Exhibition @ MFA Weaving together artworks by four artists made over centuries and across the Atlantic, this exhibition follows a genealogical thread united by the sea. Ends 11/9.

Ongoing - ‘Rituals for Remembering’ Exhibition @ MFA This exhibition brings together works by influential Cuban artists María Magdalena Campos-Pons and Ana Mendieta whose art explores the notions of displacement, exile, and nature as transformative tool. Ends 2/15/2026.

Ongoing - ‘Portia Zvavahera: Hidden Battles / Hondo dzakavanzika’ Exhibition @ ICA Inspired by Indigenous Shona and African Pentecostal faith traditions, Zimbabwean artist Portia Zvavahera’s exhibition centers around wild animals, where bulls, snakes, rats, and owls represent mysterious forces and potential threats. Ends 1/19/2026.

Ongoing - ‘Sketch, Shade, Smudge: Drawing from Gray to Black’ Exhibition @ Harvard Art Museums This exhibition celebrates the act of drawing using familiar tools—charcoal, chalk, crayon, and graphite, showcasing how simple tools can be powerful vehicles for artistic expression. Ends 1/18/2026.

Ongoing - ‘Jung Yeondoo: Building Dreams’ Exhibition @ Peabody Essex Museum Photographing ordinary families and individuals, Artist Jung Yeondoo’s work invites viewers to take a closer look at those strangers we don’t notice and imagine their dreams. Ends 1/25/2026.

Ongoing - ‘Draw Me Ishmael: The Book Arts of Moby Dick’ Exhibition @ Peabody Essex Museum ‘Draw Me Ishmael’ is the first exhibition focused on the book arts of the hundreds of editions of Herman Melville’s Moby Dick - the most persistently pictured of all American novels. Ends 3/29/2026.

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