Fluff, Freedom & Fall Fun:
Boston Weekend Guide | Sep 18–20
From major festivals to live music, comedy, and early fall fun, Boston is buzzing with energy this weekend. Explore standout events and neighborhood happenings across the city.
Here are someAMAZINGthings to do this weekend!
Fall is starting to settle into Greater Boston, and the weekend is packed with reasons to get out and explore. From the Boston Freedom Rally and Somerville’s quirky What the Fluff? Festival to live music, film, comedy, and seasonal celebrations, September 18–20 brings plenty of ways to experience the city with friends.
🌿 Boston Freedom Rally 2026 | September 18–19
🕕 Fri, 3:00–8:00 PM | Sat, 12:00–8:00 PM | 📍 Boston Common | 💲 Free
The Boston Freedom Rally takes over Boston Common for two days of live music, local vendors, speakers, and cannabis culture. Celebrate its 37th year with performances, education, and advocacy under this year’s Seeds of Reform theme.
🥃 Boston Rum Week at Bully Boy Distillers | September 18
🕕 6:00–10:00 PM | 📍 Bully Boy Distillers | 🔞 21+
Kick off Boston Rum Week with specialty cocktails, free rum samples, a limited-edition release, and a behind-the-scenes distillery talk. Grab fried chicken and boozy rum custard, then stick around for cornhole, pinball, and Guess the Proof.
🎤 Dermot Kennedy: The Weight of the Woods Tour | September 18
🕕 8:00 PM | 📍 MGM Music Hall at Fenway
Dermot Kennedy brings The Weight of the Woods Tour to Fenway for a night of powerful vocals, emotional anthems, and fan favorites, with special guest Jonah Kagen joining the lineup.
🍂 Boston Landing Fall Festival | September 19
🕕 11:00 AM–4:00 PM | 📍 Boston Landing | 💲 Free
Saddle up for fall at Boston Landing with live music, a DJ, line dancing, BBQ, drinks, and Western-inspired fun. Expect pony rides, pumpkin decorating, a vintage photo booth, crafts, and plenty of ways to celebrate the season.
🎬 42nd Boston Film Festival | September 16–21
📍 Various Boston Venues | 💲 Prices Vary
The Boston Film Festival returns for its 42nd year with world premieres, documentaries, shorts, special screenings, and filmmaker events. Weekend highlights include Adventure Time: Side Quests, A Minor Time, Bolio, Beneath the Blue Suburban Skies, and more.
🍬 What the Fluff? Festival | September 19
🕕 1:00–5:00 PM | 📍 Union Square, Somerville | 💲 Free
Celebrate 21 years of What the Fluff?, Somerville’s wildly quirky festival honoring the invention of Marshmallow Fluff. Expect Fluff-inspired food, old-school midway games, live entertainment, art, local vendors, and plenty of sticky surprises throughout Union Square.
🩰 Boston Ballet: Fall Experience | September 18–20
🕕 Friday, 7:30 PM | Saturday, 1:30 & 7:30 PM | Sunday, 1:30 PM | 📍 Citizens Opera House
Experience Boston Ballet with a contemporary twist as Fall Experience brings humor, live music, bold movement, and theatrical surprises to the stage. The program pairs Alexander Ekman’s playful Cacti with Akram Khan’s powerful Vertical Road (Reimagined) 2023.
🎸 The Wooten Brothers | September 20
🕕 7:00 PM | 📍 Citizens House of Blues Boston
Catch The Wooten Brothers live at House of Blues for a night of funk, jazz, soul, and powerhouse musicianship. Led by Grammy-winning bassist Victor Wooten, the group brings a high-energy Sunday night show to Fenway.
😂 The Comedy Studio’s Tour of Harvard Square + Comedy Show | September 20
🕕 Tour, 4:00 PM | Show, 6:00 PM | 📍 The Comedy Studio | 👨👩👧 All Ages
See Harvard Square through the eyes of Boston comedians on a walking tour packed with local history, quirky stories, and plenty of laughs. Then head to The Comedy Studio for a live stand-up show to close out the evening.
From festivals and live music to film, comedy, and the first signs of fall, there’s plenty to fill your weekend around Greater Boston. Pick your favorites, grab your friends, and get out there. We’ll be back with more ways to experience the city next weekend.
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By Boston Event Guide - It's Buzz