Downtown Worker Appreciation Day
Downtown Worker Appreciation Day Returns Thursday, May 15, 2025
Join us for Portland’s largest celebration of downtown employees. This annual springtime event is all about you — with giveaways, refreshments, and heartfelt appreciation. It’s our way of saying thank you before the busy summer season kicks off. So, round up your coworkers for Downtown Worker Appreciation Day. *Rain Date: Thursday, May 22, 2025
Two Events. One Day of Appreciation.
There are two chances to celebrate in 2025, and you’re invited to both! Spend your midday break at the Lunchtime Event in Monument Square from 11 a.m. to 1 p.m., then head to Boothby Square after work for drink discounts and more fun at Happy Hour from 4 p.m. to 6 p.m.
2025 Highlights
In 2024, Portland Downtown hosted the event in Monument Square, where downtown workers received goodie bags containing mini succulents, snacks, and downtown coupon booklets. Over a dozen area businesses and organizations joined in, offering swag, iced coffee, and chocolate-covered snacks. The festivities included live music, lawn games, portrait drawings, tarot card readings, and even an energetic outdoor cycling class right in the square!
Click the photos to view the full 2024 gallery

Get Your Business Involved Next Year
Are you interested in becoming a sponsor for a Portland Downtown event or another exciting program? We’d love to hear from you! Email us at info@portlandmaine.com with “Sponsor Interest” in the subject line. Share your business or organization’s sponsorship goals, and we’ll help match you with the perfect event or program!