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First Friday Art Walk
When: Friday, June 5, 2026
Where: Downtown Portland
What: Portland's galleries, museums, artists, and performers open their doors for a free evening of art, music, and community.
Summer Sunsets Live
When: Thursday, June 5, 2026 5p-9p
Where: Thompsons Point
What: Local food trucks, live music, cold drinks, and unbeatable sunset views.
https://thompsonspoint.com/event/summer-sunsets-live/2026-06-05
Portland Farmers' Market
When: Saturday Mornings 7a-1p
Where: Deering Oaks Park
What: One of Maine's most beloved farmers markets featuring local produce, flowers, baked goods, and artisans.
Falmouth Farmers Market
When: Thursdays 11a-3p
Where: Marine Park on Scranton Ave
What: Enjoy fresh local local produce, flowers, baked goods, and artisans.
Shipyard 1/2 Marathon & 5k
When: Saturday, June 6, 2026
Where: Old Port
What: Shipyard Old Port 1/2 Marathon & 5k. One of Portland's signature running events featuring scenic routes through the city and waterfront.
Farm Day at Skyline Farm
When: Sunday, June 7, 2026 11a-2p
Where: 95 The Lane, North Yarmouth
What: Farm Day is a community event celebrating farm life. There will be livestock, carriage rides, games and more.
June Events
🌽 Portland Farmers Market
Date: Saturdays & Wednesdays throughout June
Town: Portland
Description: One of Maine's premier farmers markets featuring local produce, flowers, baked goods, prepared foods, and Maine-made products.
Event Details: https://www.portlandmainefarmersmarket.org/
🌆 Portland Downtown Events
Date: Ongoing throughout June
Town: Portland
Description: Live music, community events, outdoor activities, and cultural programming throughout Portland's downtown neighborhoods.
Event Details: https://www.portlandoldport.com/events/?utm_source=chatgpt.com
⛵️Windjammer Days
Date: Through June 27th
Town: Boothbay Harbor
Description: The 64th Annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy. Various events and celebrations.
Event Details: https://www.boothbayharborwindjammerdays.org/schedule
🌅Summer Sunsets LIVE
Date: June 25th and ongoing 5pm to sunset
Town: Portland
Description: Portland’s go-to waterfront hangout—bringing together the best of local food trucks, live music, cold drinks, and unbeatable sunset views.
Each week features a rotating lineup of musicians, performers, and local vendors, plus a curated selection of beer, cocktails, and NA options from our favorite partners.
Event Details: https://thompsonspoint.com/event/summer-sunsets-live/2026-06-25/
🦪 Maine Oyster Festival
Date: June 27-28
Town: Freeport
Description: A two-day celebration of Maine oysters, local seafood, vendors, and live entertainment.
Event Details: https://www.visitfreeport.com/events/