Old Port Fest Weekend Guide June 7th-9th

It’s Portland’s Annual Summer Kickoff Weekend so get ready for tons of activities, music, and food! Plus, the 2019 Old Port Festival is this Sunday, June 9th. Sadly, this is the last one, so come down and make it the best! 


It’s National Donut Day and Portland is celebrating! Check out our five favorite donut shops in Portland and grab a donut for yourself!

Check out Square Hop, Portland’s local music and entertainment festival that spans four of Old Port parks. Stop by Post Office Park, Monument Square, Congress Square Park, and Longfellow Square from 6-8 pm for some of the best live performances Portland has to offer!


From 11 am-3 pm wander the sixth Walk the Working Waterfront self guided walking tour! This tour celebrates the hardworking people and businesses of Portland’s ocean economy and allows visitors to tour commercial vessels and explore the many businesses of historic Commercial Street.

It’s Shop for a Cause Day, from 11 am-1 pm, here in Portland so if you’re looking for a reason to shop Downtown this is it! A portion of all proceeds from participating businesses goes to the local non-profit LearningWorks. LearningWorks provides Southern Maine with community-based education programs for all ages.

New Orleans band Tank and the Bangas play their mix of soul, hip-hop, R&B, and jazz at Port City Music Hall at 8pm. This performance is for all ages! Grab your tickets now because doors open at 7 pm!


Stop by the farewell Old Port Festival from 11 am to 5 pm, rain or shine in Downtown Portland! You won’t want to miss the parade that begins at the top of Exchange Street at 11 am. Visit the Old Port Festival for tons of music, food, kid’s activities, and local arts and crafts!

If you want to get away from the crowds for a bit grab some tickets for Dad and Daughter Day hosted by the Portland Sea Dogs from 10 am-3 pm!

On Peaks Island Reggae Sunday will be in full swing from 11:30 am-5 pm. Beer and Rum Buckets will be available!

Sunday on the Boulevard closes down Baxter Boulevard to cars from 9 am-4 pm. It’s a great place for a bike ride or afternoon stroll.

If you’re not ready to go home after the Old Port Fest swing by the Post Port Farewell Party held at the Whiskey Barrel. There will be free pizza from 6-9 pm, corn hole, and life sized beer pong! The party goes from June 9th at 12 pm to June 10th at 1 am.