Shoppers and locals are already marking calendars as Annapolis Pride announces Ryan Cassata as Grand Marshal and headline entertainer for the Saturday, Oct. 3 parade and festival , a high-energy, visible celebration of the local LGBTQIA+ community that promises music, speeches, and community spirit.

Essential Takeaways

  • Grand Marshal named: Ryan Cassata, award-winning singer-songwriter and trans activist, will lead the parade and headline the festival.
  • When and where: Parade starts at 11 a.m. on Saturday, 3 October; festival follows at noon at the Bates Athletic Complex.
  • Route and vibe: Parade begins at Calvert and Bladen, circles Church Circle, continues up West Street and finishes at Amos Garrett Blvd , easy to watch and family-friendly.
  • Theme and art: 2026 theme is "United In Pride, Together We Thrive," with a new logo by queer artist Oli Bennan; expect colourful, community-led programming.
  • Visibility and impact: Cassata’s presence underscores a focus on trans representation and education at this year’s event.

A headline pick that signals purpose and punch

Ryan Cassata’s appointment as Grand Marshal is both a musical booking and a statement. He’s known for a warm, authentic stage presence and a lived story that’s been shared on national platforms, so his name brings attention and gravitas. Organisers told local outlets they wanted someone who could entertain and speak to the broader social stakes , and Cassata fits the bill.

When to go and what to expect on the day

Plan to arrive early: the parade steps off at 11 a.m. and moves through downtown, which makes for easy viewing along Church Circle and West Street. The festival begins at noon at Bates Athletic Complex, with room for stages, stalls, and activities. According to event pages, you’ll find food, local vendors and community groups , everything that turns a parade into a proper street party.

Why this matters: representation, education and music

Cassata’s career mixes music with advocacy, and his appearance highlights trans visibility at a time when such representation feels urgent. He’s performed widely, from SXSW to Jazz at Lincoln Center, and has used his platform in schools and national forums. That background suggests the festival will be part celebration, part civic conversation , expect remarks and sets that balance joy and context.

Theme, look and local creative energy

This year’s theme, "United In Pride, Together We Thrive," and a specially designed logo by Oli Bennan promise a cohesive look across promotions and floats. It’s the sort of theme that helps small groups and larger organisations coordinate banners and costumes, so if you’re marching or watching, pick colours and messages that connect to the theme for fuller impact.

How to make the most of Annapolis Pride

If you’re attending, wear layers , October weather can surprise you , and bring a small chair or blanket for the festival. If you want to join a contingent, check parade registration details on the organisers’ pages and book vendor space early. For families, early arrival means better spots and calmer crowds; volunteers and local info booths will help if you’re unsure where to go.

It's a small change that can make every presence at Pride feel louder and safer.

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