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Summer is definitely not over! There’s still a TON of summer fun happening here in Portland—especially this weekend!
Start your weekend off with the Saint Peter’s Annual Italian Bazaar, where you can savor delicious Italian fare and dance to live music in the heart of Portland’s “Little Italy.” Next up, dive into the Portland’s music scene with Guster’s epic three-night On The Ocean Festival at Thompson’s Point, featuring a stellar lineup including Grace Potter and Toad the Wet Sprocket. Tie up your weekend with some summer fun at Camp Allagash for some nostalgic summer camp activities and unique brewery experiences!
Here’s The Weekend Guide for Friday, August 9th – Sunday, August 11th, 2024
Friday the 9th
Working Title Tour & Tasting with Master Distiller Graham Hamblett | Three of Strong Spirits | 6:00 PM – 8:00 PM
An exclusive tour and tasting event at Three of Strong Spirits with Master Distiller Graham Hamblett. Discover the creative process behind their Working Title Series and enjoy a sneak peek tasting of Working Title Five in honor of their 5th Anniversary Month. Get an insider’s look at how each unique rum is crafted and ask Graham your burning questions. After the tour, indulge in a guided tasting of their limited editions, finishing with the Take Five Reserve Rum before its official release. Participants will also receive a $5 gift card and have the chance to purchase a bottle before anyone else. Tickets.
Toby McAllister | Wilson County Barbecue| 5:00 PM – 8:00 PM
Join at Wilson County Barbecue for a lively evening on the patio with Toby McAllister! Known as the founding member of Sparks The Rescue, Toby has been rocking out since he could hold a guitar. After touring the world with his band, he settled back in Maine, drawing inspiration from the pandemic to release his first solo EP, Daydreamin. Now, he’s back with Autumn Skies, a mix of life, love, and rock & roll, featuring the rhythm section of Sparks and some local talent. Toby’s shared the stage with big names like Drake White and Billy Bob Thornton, and he’s ready to bring his infectious energy to Wilson County. Don’t miss this chance to enjoy live music, great BBQ, and the perfect summer vibe!
Bonerama | One Longfellow Square | 8:00 PM Show
Get ready for a night of brass, funk, and rock with Bonerama! This standing room show is a celebration of 25 years of New Orleans’ finest brass funk rock. Led by trombone master Mark Mullins, the band features Greg Hicks and Chris Butcher on trombones, Bert Cotton on guitar, Matt Perrine on sousaphone, and Eric Bolivar on drums. Known for their unique blend of brass, funk, soul, rock, and blues, Bonerama delivers powerful sounds that you have to hear to believe. With limited seating available, be prepared to get up and dance! Tickets.
Maine Outdoor Film Festival | Maine Craft Distilling | 8:00 PM Films Begin
Join for a magical evening under the stars with the Maine Outdoor Film Festival! Enjoy a curated selection of outdoor films from Maine and around the world, shown outdoors in a perfect summer setting at Maine Craft Distilling. Doors open at 7:00 PM, and the films start rolling at 8:00 PM. This all-ages event requires pre-registration due to limited space. Bring a friend, grab a drink, and immerse yourself in cinematic adventures! Tickets.
Saturday the 10th
Saint Peter’s Annual Italian Bazaar | 72 Federal Street | 5:00 PM – 9:30 PM (Repeats Sunday from 1 PM – 7 PM)
UPDATE: Friday evening has been cancelled and rescheduled to Sunday, August 11th from 1 PM – 7PM.
Experience the best of Italian culture right here in Portland at St. Peter’s Annual Italian Bazaar! This beloved street festival celebrates the vibrant heritage of St. Peter’s Parish, the heart of Portland’s “Little Italy.” Enjoy authentic Italian delights, from savory pastas to sweet cannolis, while dancing to the infectious tunes of the Jim Ciampi Band on Friday night. Saturday kicks off with a Mass led by Bishop James Ruggieri, followed by live performances from Frank Sinatra tribute artist Patrick Tobin and special guest Jimmy Mazz as Dean Martin, with accompaniment by The Fever Band, a lively 6-piece dance band. Savor the flavors, sounds, and spirit of Italy at this cherished community event!
Learn more: La Dolce Vita in Portland, Maine – St. Peter’s Annual Italian Bazaar
SailMaine Festival & Regatta | SailMaine | 10:00 AM – 8:00 PM
Set sail for a day of excitement at the SailMaine Festival & Regatta on beautiful Casco Bay! Join the fun with thrilling races featuring PHRF, 420s, J22s, and the exciting new Harbor Cruise. The day kicks off at 10 AM with the Windward Exhibition opening at the SailMaine waterfront, complete with kid’s activities and more. At 11 AM, catch the Parade of Boats and Painted Sails as it starts its scenic route. Admire the painted sails as they leave SailMaine, circle near Fish Point, and return. Watch as the 420s and J22s sail out beyond the painted sails, and larger boats make their way from Falmouth to Portland Harbor. The parade wraps up at noon. This event aims to raise $70,000 for SailMaine’s scholarship and community sailing programs. Cap off the day with an after-party at Portland Yacht Services from 5:30-8:00 PM, featuring food, drinks, and live music.
Portland Summer Jam | Congress Square Park | 5:00 PM – 8:00 PM
Dive into an electrifying Hip-Hop Jam Session led by Damn Jamn, where musicians, DJs, and beat makers are invited to join in the fun. Catch live performances from the talented ReadyRockDee from New York and Moose Harris from Louisiana, bringing their unique styles to the stage. Plus, enjoy a DJ set by Graphic Melee, who will take you on a journey through Hip-Hop history, spinning tracks from the genre’s earliest recordings.
Red Riding Hood | Children’s Museum & Theatre | 11:00 AM – 12:00 PM + 3:00 PM – 4:00 PM (Multiple Dates)
Get ready for a whimsical twist on a classic tale at the Children’s Museum & Theatre with Red Riding Hood! Watch as the world’s greatest actor, Wolfgang, gets interrupted by a mysterious package delivery. With the delivery person joining the fun in a red beanie, this unexpected duo brings a hilarious and fast-paced retelling of Red Riding Hood to life. Expect plenty of surprises, cleverness, and a courageous Red who’s ready to outsmart the hungry wolf. It’s a fairy tale like no other—full of laughs and unexpected turns. Perfect for a family outing that promises fun for all ages! Tickets.
Bonnie & The Cats | The Porthole | 2:00 – 5:00 PM
Guster On The Ocean | Thompson’s Point | 3:00 PM Doors (Repeats Sunday)
Guster on the Ocean is back for its 6th year! Set to be unforgettable with three nights of Guster and an amazing lineup of Grace Potter, Kevin Morby, Toad the Wet Sprocket, The Dip, Trousdale, Sunny War, and The Wolff Sisters. Kick off the festival with a Friday night bash at the State Theatre, featuring karaoke and costumes—come dressed as your favorite rock star and maybe grab a mic! Plus, enjoy Bissell Brothers Guster beer, the B-stage at Thompson’s Point, Guster “moth” storytellers, and the Kids’ Zone. Don’t miss the special 25th Anniversary performance of “Lost & Gone Forever” on Sunday. Rrock out and celebrate music, positivity, and community together! Tickets.
Bottoms Up! Pro Wrestling Event | Definitive Brewing Co. | 6:30 PM – 9:30 PM
Bottoms Up! Pro Wrestling is hitting Definitive Brewing Company for an evening of action-packed excitement! Hosted by New World Extreme Wrestling, this wild event promises high-flying moves, intense rivalries, and unforgettable moments. Doors open at 6:30 PM, with the bell ringing at 7:30 PM—come early to enjoy beer specials and delicious bites from Terra Firma Food Truck! This all-ages show is a perfect summer event for wrestling fans and newcomers alike. Tickets.
Sunday the 11th
Camp Allagash | Allagash Brewing Co. | All Day – Happening until Saturday 8/17
Camp Allagash is hitting Portland from August 11th – 17th, transforming Allagash Brewing into a summer camp extravaganza! Dive into activities like tie-dying, making friendship bracelets, and “fishing” for fun. Sunday highlights include: Center for Wildlife animal visit from noon-3 PM, frozen treats, and toy axe throwing all day. Most activities are free with your visit to the tasting room, and some special events require tickets. Check out the full schedule online and get ready for a week of camp-inspired fun!
Princess & Pirate Day | Hadlock Field | 1:00 PM
Arrrghhh you ready for a fun tea party with princess and pirates? Join the Portland Sea Dogs at Hadlock Field for tea and cookies, plus a meet and greet with princesses and pirates in the Park Ave Plaza! Kids are encouraged to come to the game dressed as their favorite princess or pirate and to participate in a pre-game parade directly after the tea party. Tickets.
Who D&Dunnit: Presented by Lobster Role LIVE | Empire Comedy Club | 6:00 PM – 8:30 PM
Join the cast of Lobster Role as they tackle a hilariously twisted murder mystery at Empire Manor. Six heroes gather for an honor, but deceit lurks within these walls. Audience members receive envelopes with clues to help solve the mystery, and VIP seats offer prime spots and special show favors. Enjoy a D8 rollable drink menu, merchandise, and stand-up comedy to kick off the evening. Will you crack the case before the final curtain? Tickets.
Lucas Roy | Luna Rooftop Bar | 6:00 PM – 9:00 PM
Photo: @nickvigue
Catch Portland’s own Lucas Roy live at Luna Rooftop Bar for an unforgettable night of music! Known for his impressive performances with Jason Mraz and Ryan Hurd, and his debut EP “Too Far Gone,” Lucas is set to enchant with his soulful tunes. From Reykjavik to Nashville, his journey has been filled with musical magic. Don’t miss this chance to see him under the stars at one of Portland’s coolest spots!
For more events head to our Events Calendar here.
