Anneke Van Mierlo of Portland leads a large puppet down Exchange Street during the Shoestring Theater’s parade to kick off a previous Old Port Festival. Staff photo by Derek Davis

The Shoestring Theater’s larger-than-life big-headed puppets on sticks are leading their 46th and final Old Port Festival parade, kicking off a jam-packed day of music, food and fun in Portland’s Old Port – and unofficially welcoming summer. If this parade is a sight you haven’t seen, June 9 is your last chance.

“It’s definitely one of the community’s favorite parts of the day,” said Casey Gilbert, executive director of Portland Downtown. “It’s a magical experience.”

Beginning with the 11 a.m. parade from the Press Hotel down Exchange Street to Fore Street and Silver Street, the Old Port Festival is a six-hour party downtown. Gilbert has said that the event is ending because it has “achieved its mission” of getting people to come to the Old Port – now a bustling neighborhood of businesses beloved by tourists for its quaint feel and cobblestone streets.

“Our mission is to make it the best yet and send the Old Port Festival off on a fond farewell,” Gilbert said. “People can expect the same level of fun and entertainment as in previous years and perhaps a few surprises.”

The Old Port Festival features four music stages. Photo by Amy Paradysz

The Old Port Festival is an urban street party with streets closed to vehicle traffic and four stages of live music from noon to 5 p.m. The Coast 93.1 and WPOR 100.9 Stage is at Middle and Temple streets, the WCLU 98.9 Stage at Free and Silver streets, talented student musicians at the Maine Academy of Modern Music Stage at Commercial and Dana streets and child-focused entertainment in the shade at Post Office Park at Middle and Temple streets.

In addition to all the shops and restaurants already in the Old Port – which, blessedly, often have air conditioning and restrooms open to customers – about 250 vendors and food trucks line the streets. Annual food favorites include fried dough, hand-cut French fries, grilled sausages and fresh-squeezed lemonade.

Out-of-town visitors might want to make a weekend of it, as the Old Port Festival is the third day of Portland’s Summer Kickoff Weekend. The party gets started that Friday night, June 7, with Square Hop (6-8 p.m.) featuring four performances in four iconic city parks: Monument Square, Congress Square, Longfellow Square and Post Office Park. Saturday, June 8, is Shop for a Cause Day, with a portion of proceeds going to a local charity. That same day, Walk the Working Waterfront is a chance to explore the fisheries and other businesses on the wharves and piers lining Commercial Street from 11 a.m. to 3 p.m.

“There’s something to do every day,” Gilbert said, “and, of course, plenty of shops, restaurants and sights to see.”

For the full schedule, go to

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