Shoppers and neighbours are turning out as Westport Pride Fest returns for Year 3 , founders Keith and Jessie Dias were honoured at the Massachusetts State House, and the free, family-friendly festival moves to town property on Sunday 28 June, promising live music, food trucks and a real sense of community.

Essential Takeaways

  • Founders recognised: Keith and Jessie Dias received Commonwealth Pride Awards for community leadership and organising Westport Pride Fest.
  • New home on town land: The festival shifts to Alice A. Macomber School grounds at 154 Gifford Road, signalling local acceptance.
  • Event basics: Free to attend, rain or shine, 11am–5pm on 28 June, with free parking, live entertainment, crafters, vendors and food trucks.
  • Local backing: Sponsored by Senator Michael Rodrigues, Westport Federal Credit Union and others, giving the event momentum and visibility.
  • Small-business angle: The Diases own The Cat And Raven, an LGBTQ-owned crystal and psychic shop that’s expanding with a grand re-opening the same weekend.

Why the move to town property matters

Moving Pride Fest onto town-owned land is more than logistics; it’s symbolic and visible. Holding the event at the Alice A. Macomber School gives it a civic address, which organisers say sends a message of inclusion to residents who might otherwise never step into a Pride celebration. You can almost feel the relief in the planning: fewer permit wrangles, clearer access and a sturdier sense of belonging.

Organisers told local media the plan from the start was to anchor the festival in a public space. After two years of growing attendance, finding a permanent, central site means the fest can scale up entertainment and hospitality , and that’s why food trucks are joining for the first time this year. If you’re coming with kids or a mobility aid, the school site should make getting around easier and more comfortable.

Founders honoured at the State House , what that signals

Keith and Jessie Dias were nominated by Senator Michael Rodrigues and Representative Steven Ouellette and received awards at the inaugural Commonwealth Pride ceremony in Boston. Recognition at the State House puts Westport Pride on the map and highlights grassroots organising as state-level leadership. That kind of acknowledgement can unlock sponsorship, volunteers and goodwill.

There’s also a personal angle: the Diases run The Cat And Raven on Main Road, an LGBTQ-owned small business that’s expanding and hosting a grand re-opening the same weekend. Local shops getting awards helps knit together commerce and community , people come for the festival and stay to support nearby businesses.

What to expect on the day , practical tips

Expect a laid-back, walkable festival with a mix of craft stalls, local vendors and live acts. With the new food-truck element, bring cash or ensure your cards work at mobile points of sale. The event runs 11am to 5pm rain or shine, so pack a lightweight waterproof or a sun hat depending on the forecast.

If you’re driving, take advantage of free parking but arrive early for the best spots. For anyone attending with children or pets, check event guidance in advance , noisy stages and crowds suit some families and not others. For stallholders and performers, organisers recommend arriving early to set up and scouting the site layout beforehand.

How this fits into wider Pride trends in small towns

Small-town Pride events are growing across the US and gaining civic recognition, and Westport’s move reflects that trend. Local festivals are shifting from grassroots garage gatherings to professionally supported community celebrations, often with municipal buy-in. That’s good news for visibility and safety, though it can mean events feel more curated than they once did.

Still, many residents say the trade-off is worth it: more attendees, better amenities and a cleaner message that LGBTQ+ people are part of the town fabric. Expect Westport’s model , a free, accessible festival anchored by local businesses and elected-official support , to be one other small towns look to emulate.

Supporting local LGBTQ-owned business on Pride weekend

If you want to make the weekend count beyond the festival, pop into The Cat And Raven on Main Road to celebrate the shop’s grand re-opening. Buying from LGBTQ-owned businesses keeps money local and rewards entrepreneurs who put time into community-building. Even a small purchase or a social media shout-out helps.

And if you can’t make it on the day, consider donating time or expertise to next year’s organisers; festivals like this run on volunteers and sustained goodwill. It’s a simple way to ensure Pride stays free, friendly and for everyone.

It's a small change that can make every celebration more welcoming and visibly local.

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