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The Massachusetts Bear Contest Weekend at the Alley Bar arrives October 9-10, 2026! Yes, we did say “Massachusetts Bear!” BIGGER, BEARER, BETTER: Join us on Saturday, October 10, 2026, at the Alley Bar, 14 Pi Alley, Boston, for the Massachusetts Bear 2027 Contest! Starting at 7 p.m., there will be a warm-up party with go-go Bears and entertainment leading up to the main event at 9 p.m. The contest showcases the individualities, interests, and talents of our contestants, culminating with the reveal of the new Massachusetts Bear titleholder for the coming 2027 year. Co-hosted by Dave Sawyer, this will be a night not to be missed! Advance tickets are available through Eventbrite ($20). You are also invited to join us on Friday, October 9, 8 p.m., for our Contestant Meet and Greet. Our Friday evening event is a free event at which you will have the opportunity to meet our contestants in an informal setting. Follow us on Facebook, Instagram, and/or Bluesky for updates, event participant reveals, and more! This is a 21+ event, proper ID required.

Event Organizer