MR BEAR SAN DIEGO

Mr. Bear San Diego 2025 
Jimmy Trimble
(He/Him)

  • San Diego Bootblack, Leather Bear, and Leather (MX | MS | MR) Contest Week
    San Diego Bootblack, Leather Bear, and Leather (MX | MS | MR) Contest Week. March 10 - 15, 2026

    It’s here again! Come out and join the Contestants, Judges, Fans, and Support Businesses in this years largest Leather Event Week.

    Summary of Events

    What: Contestant Interviews
    Where: Pride Room @ Number One Fifth Ave. (3845 Fifth Ave)
    When: 6:30 p.m. March 10th, 2026
    Followed By: Leather Pictionary on the Patio

    What: Naughty Bingo Leather Invasion
    Where: Negociant Winery (1263 University Ave)
    When: 7:00 – 9:00 p.m. March 11th, 2026

    What: Skate Night
    Where: Ringers Roller Rink (6060 Federal Blvd)
    When: 6:00 – 9:00 p.m. March 12th, 2026

    What: Meet & Greet
    Where: AWOL (1475 University)
    When: 7:00 p.m. March 13th, 2026

    What: Open Shine
    Where: The Brass Rail (3796 Fifth Ave)
    When: 9:00 – 11:30 p.m. March 13th, 2026

    What: Volunteer Brunch
    Where: Rosemary & Thyme Cafe (1475 University)
    When: 10:00 a.m. March 15th, 2026

    Culminating: Leather Contest
    Where: Rich’s (1051 University)
    When: 1:00 – 5:00 p.m. March 14th, 2025
    Suggested Donation: $20 (Pay What You Can- At the Door)

  • 2026 Bears San Diego Chili Cookoff And Cub In-VEST-iture!

    Join us Sunday, February 15th, for our annual Chili Cookoff Contest! Come on out and have some fantastic grub, choosing from a variety of chili styles and heat. Currently at 7! contestants this year. You’ll find us at the Loft, running from 2 PM to 5 PM, or we run out of chili, of course. Bring your appetite, grab a beverage from the bar, and enjoy yourself! Always a great time and everyone who joins in the feast gets a vote.

    2026 Bears San Diego Chili Cookoff at the Loft in Hillcrest!

  • San Diego Leather Bear and San Diego Bootblack Leather

    Would you like to get involved more with Bears San Diego? Here is a prime opportunity to do so. Applications are due January 31, 2026. Do not hesitate to get in contact with one of the Bears San Diego Board or the current San Diego Leather Bear, Giovanni T!

    March 13-15, 2026 at Richs on University Ave. Applications for San Diego Leather Bear are due January 31!
  • Dinner Night for January!
    Meet us 6:15p to 8:00p at the Chicken Pie Shop, 2633 El Cajon Blvd, San Diego, CA 92104.

    Join us for a night at one of our favorite comfort food locations. This one starts earlier than normal because the restaurant itself closes earlier than some of our other favorite location.

  • Merry Christmas and Happy Holidays
    Happy Holidays from Bears San Diego

    Everyone at the Board of Bears San Diego wishes you and all you cherish the warmest of wishes and a Happy New Year to Come!