Spend the Weekend in Portland, Maine’s Vibrant and Welcoming Community

2 Days of Fun LGBTQ+ Friendly Activities and Events in Coastal Maine

Portland, Maine—a city that just loves love. From local traditions like the Valentine’s Day Bandit posting paper hearts all around town to the new Hearts of Pine soccer team, our coastal gem wears its heart on its sleeve. Greater Portland’s vibrant queer community is more than welcomed and accepted—it’s woven into the fabric of the region. Portland’s recognition as one of America’s friendliest destinations for LGBTQ+ travelers has earned top spots in lists like “7 Underrated But Colorful Pride Parades To Attend In 2024” by The Travel.

Consistently featured in travel publications and celebrated by influential LGBTQ+ voices, Portland blends historic charm with progressive energy, colorful rainbow crosswalks come together alongside cobblestone streets in the seaside, Old Port. Supportive local businesses and high-energy cultural vibes set a backdrop of drag brunches, queer nightlife, and inclusive festivities. Portland warmly welcomes everyone.

Day 1

Portland’s accessible downtown invites exploration on foot, covering just 3.5 miles end-to-end. Enjoy strolling along cobblestone streets adorned with rainbow crosswalks, inclusive window dressings, and festive decorations that signal a city proud of its diversity.

Morning

Start your day by grabbing coffee and breakfast at a local sweet treat or coffee shop in Downtown Portland. Come for the welcoming atmosphere and stay for the locally-roasted beans and artisanal brews. Afterward, drive or cycle to Fort Williams Park to see Maine’s iconic Portland Head Light. Guided tours & cruises are an easy way to get up close and personal with landmarks with a friendly local Mainer.

Explore the scenic grounds, historical markers, and breathtaking ocean vistas at one of the nation’s oldest lighthouses, celebrating both history and natural beauty. Don’t forget to stop by the Bite Into Maine kiosk at Portland Head Light…we are the land of lighthouses and lobsters after all.

Afternoon

Head back downtown for lunch along the bustling Working Waterfront and grab a trap-to-table delicacy caught straight from Casco Bay. Fresh seafood and inclusive atmospheres anywhere you go downtown, Portland is a safe a welcoming environment. Spend the afternoon shopping at eclectic boutiques, vinyl and local music stores as well as souvenir shops, where rainbow-themed apparel, quirky gifts, and inclusive apparel is widely highlighted along with Portland’s spirit of authenticity.

Evening

As evening falls, attend a live performance at Merrill Auditorium or State Theatre—both iconic venues known for hosting legendary queer performers like Tig Notaro and iconic celebrities including Jonathan Van Ness, who recently spotlighted Portland’s charm on TikTok.

We invited Brian from @cornersofboston up over the Winter to visit the region and explore the LGBTQ+ stories and vibes of the city.

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A post shared by Brian Pu Ruiz – Cornersofboston (@cornersofboston)

Day 2

Morning

Kickstart your second day with an unforgettable drag brunch experience at Apres or Batson River Brewing, offering dazzling performances, artisan mimosas, and delightfully spicy Bloody Marys. For a change of pace, venture onto the Bay with Casco Bay Lines and visit Buyers & Sons Long Island Bakehouse on Long Island. Their bloodys have bloody marys ice cubes, so the your bevvy stays strong.

There you’ll enjoy fresh pastries and whoopie pies for a treat with island breezes and fun-loving community vibes—a perfect getaway from the mainland. There’s a few quick island escape you can make for a daytrip to make the most of your trip.

40 minute ferry from Portland

20 minutes from Portland

1 hour from Portland

Afternoon

Returning to Portland’s mainland, download the Creative Portland Art App for a self-guided tour. Wander through the Arts District to admire murals, sculptures, and public art installations celebrating the city’s cultural diversity.

Explore galleries, studios, and green space all across Portland (and beyond) many of which proudly display works by LGBTQ+ artists.

Evening

Dive into Portland’s renowned culinary scene with dinner elevated prix fix experiences and chef’s table masterpieces. Portland is a foodie city and at Green Elephant, widely celebrated as Maine’s healthiest restaurant, you’ll uncover a mouthwatering vegetarian menu. The inspiration for their food began in Thailand and grew to include numerous Asian influences.

Explore the Arts District while you food-hop and stop for a photo op at a local landmark or iconic street art to capture the culture of our diverse and talented tapestry of local makers.

@visitportland

You know you want to explore the art and culture around every corner in Portland, Maine. Murals, statues, sculptures, and special events set spring ablaze with new life. You’re not going to want to miss a minute of it ✨ #art #maine #newengland #fyp #seagulls #streetart #mural

♬ Good Life – OneRepublic

Late Night

Conclude your vibrant Portland weekend by exploring the lively LGBTQ+ nightlife. Begin at Blackstones, the city’s oldest LGBTQ+ bar, then head to chic hotel bars like the Luna Rooftop Bar at the Canopy Hotel for breathtaking views and craft cocktails. Portland’s vibrant rooftop bar scene and welcoming hotel lounges provide the perfect finale for your inclusive, festive weekend.