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Ray Routhier

Portland Press Herald staff writer Ray Routhier will try anything. Once. During 20 years at the Press Herald he’s been equally attracted to stories that are unusually quirky and seemingly mundane. He’s taken rides on garbage trucks, sought out the mother of two rock stars, dug clams, raked blueberries, and spent time with the family of bedridden man who finds strength in music. Nothing too dangerous mind you, just adventurous enough to find the stories of real Mainers doing real cool things.

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Posted: April 29, 2019

Portland’s outdoor entertainment heats up – even though the weather hasn’t

Written by: Ray Routhier

Bayside Bowl in Portland will begin hosting live music on its rooftop deck May 2 with a performance from The A-Beez, a Boston-based soul and funk group. The venue’s outdoor film series starts May 15 with “The Big Lebowski.”
Photo by Tom Couture

In other parts of the country, restaurants and bars might wait until temperatures are in the 70s before they start booking bands for their outdoor patios and decks.

But in Maine, where we might not see 70s until July, and then only for a few weeks, it makes more sense to get the outdoor party started early. Following that logic, several Portland venues are kicking off their schedules of outdoor entertainment this weekend or soon after.

Bayside Bowl’s rooftop deck will begin hosting bands Thursday, while Portland Lobster Company and Congress Square Park will both have live entertainment beginning Friday. The Porthole Restaurant & Pub will begin hosting bands on its waterfront deck on May 19.

After Memorial Day, Greater Portland will be flush with bands performing in parks, on patios, on rooftops and at large summer venues like Thompson’s Point and the new Maine Savings Pavilion at Rock Row in Westbrook. But, for now, you’ve got to know where to go if you want to sip beer or cocktails on a deck while rockin’ out to a live band – and we’re here to help.


You can go up on the roof, the rooftop deck at Bayside Bowl in Portland, to be specific. The deck sits atop the bowling alley’s third story and has a capacity of 180, which means it’s bigger than some Portland bars and clubs. And the sunset views looking out toward the Back Cove and the White Mountains are spectacular. The deck features an Airstream trailer transformed into a food truck, serving tacos and other goodies. So you can eat, drink and be merry. There is no cover for the entertainment.

The deck’s music schedule kicks off at 7 p.m. Thursday with The A-Beez, a soul and funk band from Boston. Shows are every other Thursday, with Maine soul singer Gina Alibrio and members of The Red Eye Flight Crew on May 16 and the rock/funk/progressive duo Quad on May 30. The rooftop deck will also host films on Wednesdays this year, beginning on May 15 with “The Big Lebowski” followed by “Wonder Woman” on May 29.

Bayside Bowl, 58 Alder St., Portland;

The live entertainment season will start Friday in Portland’s Congress Square Park, with a performance by Circus Ole.
Photo courtesy of Friends of Congress Square Park


The Friends of Congress Square Park organize more than 150 events in the picturesque downtown space from May through October. The park is in the center of the city’s arts district, across from the Portland Museum of Art. It features a raised stage area for performers, trees and big buildings for shade and colorful benches and chairs.

The first performance in the square this season will be at 6 p.m. Friday by Circus Ole, a Maine group that includes trapeze artists, jugglers, hoop dancers, giant puppets and stilt walkers. Every Friday evening through September, the park will host live music, dance, circus or other performances, including the Maine Academy of Modern Music Showcase on May 10, clowning and puppet workshops on May 17, and the drumming of Sister Steel on May 24.

The park will also host a season-long film series on Sunday nights beginning June 2 with “Won’t You Be My Neighbor?” followed by “Rebel Without a Cause” on June 9.

Congress Square Park, corner of Congress and High streets, Portland;

Portland Lobster Company on Commercial Street will begin hosting live music for the season on its waterfront deck Friday.
Staff photo by Joel Page


The Portland Lobster Company on Commercial Street has a deck on the harbor, and all summer it is filled with local musicians, as well as people enjoying lobster rolls. The music kicks off this year at 6 p.m. Friday with the Maine blues group Blue Steel Express. The country/folk/blues sounds of Scotty River Trio will be heard Saturday afternoon from 12:30 to 3:30 p.m., and the eclectic music mix of Ryan Halliburton & The Still will be featured from 6 to 9 p.m. Saturday. There’s a band scheduled just about every night through May and into the summer, including local favorites such as Jason Spooner, the Delta Knights, Dominic Lavoie and the Mitch Alden Duo.

Portland Lobster Company, 180 Commercial St., Portland;

The Porthole on Custom House Wharf will begin hosting bands on its waterfront patio May 19.
Photo courtesy of The Porthole Restaurant & Pub


The Porthole Restaurant & Pub on Custom House Wharf gives diners a view of all the comings and goings on Portland Harbor, along with food and drinks. Live entertainment begins at 2 p.m. May 19 with the rocking sounds of Hollis Hollow, who are known to play a few slow ones, too. On May 24, the patio will host the high-energy hip-hop and dance music of SugarBox, followed by more dance music on May 25 from Stolen Mojo. Other acts scheduled include singer-songwriter Dan Merrill with sax player Darren Whtiney on May 28 and accoustic cover band Quiet Riot Act on May 30.

The Porthole Restaurant & Pub, Custom House Wharf, Portland;

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