The only thing hotter than this week’s recent rise in temperatures is this weekend’s round-up of events in Portland, Maine.
Okay, okay, a little cheesy, but the truth is that Portland is buzzing with end-of-summer excitement this weekend and you’re invited to be a part of it all. From vibrant live music performances to Oktoberfest celebrations, there’s something for everyone to enjoy. Check it all out right here!
Here’s The Weekend Guide for Friday, September 8th, 2023 – Sunday, September 10th, 2023
Friday the 8th
Negroni Month | ViA VECCHiA | All Month
Embark on a Negroni journey around the globe with Via Vecchia! Starting August 31st, join this small plates Italian restauraint for Negroni Month. Stop by to taste various Negroni twists inspired by different parts of the world. Collect stamps in your Negroni Passport for each drink and complete the tour to earn your Negroni aficionado status. Best part? Proceeds go to Slow Food, a global movement that envisions a better world through food. Sip, savor, and support a cause!
Food Truck Festival | Austin Street Brewery – Fox St. Location | 4:00 PM -8:00 PM
This is a vibrant Food Truck Festival featuring live music by Eli & Noah Smith and an array of gourmet treats from renowned food trucks: Vy Banh Mi, The Muthah Truckah, Black Salt Dining, and Ugly Dumpling Food Truck. Indulge in delicious fare, sip craft brews, and relish the lively atmosphere. Join for a day of culinary delights, music, and camaraderie.
Alive in the Root | Andy’s Old Port Pub | 8:00 PM – 11:00 PM
Experience the exceptional musical journey of Alive in the Root! This talented, multi-instrumental acoustic roots band will mesmerize you with their original compositions. An evening of poetry, harmony, and soulful melodies that will leave you spellbound.
Saturday the 9th
Definitive Brewing Co’s Oktoberfest | Definitive Brewing Co. | 12:00 AM – 8:00 PM
Get your steins and spirits ready, because it’s time to embrace your inner Wurst behavior at Definitive Brewing Co’s Oktoberfest! Join the Definitive team at their Portland location for a festive celebration of all things German, complete with beer, food, music, and endless fun. What to expect: A special Oktoberfest beer release; a mouthwatering German menu crafted by Fat Kid Culinary Productions; live music from Jim Brady starting at 1 PM, followed by the lively tunes of Mike Stackhouse from 5 PM to 7 PM; and a friendly competition with axe throwing from 1 PM to 4 PM, and Cornhole and Ring Toss games throughout. At 2 PM + 4 PM join for the Stein Holding Competition, or let your little ones participate in the Kids Stein Holding Competition at 1:30 PM and 1:45 PM. Don’t miss out on the adorable Pretzel Necklace Making activity for the kids. This event is absolutely free to attend and is open to all ages, including your four-legged friends.
Saturday Sessions | Henry’s Public House | 9:30 PM – 12:30 AM
Step into the rhythm of the weekend at Henry’s Public House for Saturday Sessions with DJ Jay-C! Prepare to be captivated by the pulsating rhythms and infectious beats expertly mixed by DJ Jay-C. Join Henry’s Public House in their upscale lounge setting where the music takes center stage, creating an atmosphere of pure musical excitement! Unwind to some fantastic tunes.
PRCC Rally 4 Recovery | Edward Payson Park | 12:00 PM – 3:00 PM
Join at the picturesque Payson Park on Back Cove for the 2023 Portland Recovery Community Center Rally 4 Recovery! This remarkable gathering is not only Maine’s biggest celebration of recovery but also a valuable resource fair that highlights organizations dedicated to supporting recovery within our communities. The theme “Recovery is for Everyone: Every Person, Every Family, Every Community” echoes throughout the event. Live music, kids’ activities, food trucks, and the annual recovery countdown will fill the day. Community partners will be present to share resources, making it a family-friendly event organized by individuals in recovery, allies, friends, and families. The Rally raises funds for the Portland Recovery Community Center (PRCC) groups, promoting wellness, recreation activities, education, and advocacy efforts.
Massive Trash Situation | Congress Square Park | 1:00 PM – 3:00 PM
Turn waste into wonder at the Massive Trash Situation event! Discover the magic of transforming (clean) upcycled trash into musical instruments and puppets of your own creation. Join forces with Inventing Trees – a performing and visual arts troupe- for this innovative experience that’s free and open to everyone. Unleash your creativity and turn trash into treasure.
Orchestre Tout Puissant Marcel Duchamp | Deering Oaks Park Bandstand | 6:00 PM
Experience the sonic revolution of the Orchestre Tout Puissant Marcel Duchamp in Deering Oaks Park! This 12-piece Swiss ensemble infuses their traveling orchestra with punk energy and global influences. Join SPACE for their second free community concert of the summer as this border-defying orchestra takes the stage. Formed in 2006 by Vincent Bertholet (Hyperculte), this orchestral project boasts a dynamic lineup that has evolved over time. With 12 members now, the ensemble has graced stages across Europe, demonstrating that “the more, the merrier” truly resonates on stage. Their sound is a blend of free jazz, post punk, high life, brass band, symphonic mixtures, and kraut rock, defying genre boundaries. Their music is a mesmerizing, almost ritualistic experience, accompanied by poignant lyrics that echo the turbulence of our world.
Sunday the 10th
Any Two Wheels ’23 | Hi-Fidelity + Urban Farm Fermentory | 2:00 PM – 5:00 PM
Rev up your engines and roll into the ultimate celebration of two-wheeled freedom! Any Two Wheels, the open-invite bike festival that’s bringing all things pedal-powered to life, is back. Gather your push bikes, choppers, tuk tuks, scramblers, and more – if it’s got two wheels, it’s invited! Get ready for a day filled with live music, awesome vendors, delectable food, and jaw-dropping prizes. Keeping the spirit of competition alive with crowd-chosen winners in various categories, including the illustrious “Bike I Wanna Ride for 15 Minutes and I’ll Give It Back I Swear” award. Sway to the rhythms of S.C.O.B.Y. & Dark Soft while savoring delectable bites from the Black Salt Food Truck. Raffle proceeds will support the Bikes for All Mainers program by Portland Gear Hub. So gear up, tune in, and let’s make this two-wheeled fiesta a ride to remember! All-ages and free-to-all event.
Deering Center Porchfest 2023! | Deering Center | 12:15 PM – 6:00 PM
A day of musical enchantment and community celebration in the heart of the Deering Center neighborhood! Porchfest is back, bringing you a feast of musical performances as talented artists turn porches into stages and notes into moments of connection. This annual event is all about the power of music to unite the community in a simple yet profound way. Come be part of a larger community coming together for a day of harmony and togetherness. Free and open to everyone.
Train Day | The Children’s Museum & Theatre of Maine | 9:00 AM – 12:00 PM
All aboard for Train Day at the Children’s Museum & Theatre of Maine! Join the Children’s Museum in partnership with the Maine Narrow Gauge Railroad for a day that’s all about the magic of trains. The excitement kicks off at 9:30 am with Train Storytime, where the Narrow Gauge Railroad Train Conductor will whisk you away on an imaginative journey through tales of trains. From 10 to 11 am, it’s Train Takeover time in the MakerSpace! Unleash your creativity and design your very own train. Let your imagination run wild as you craft a locomotive masterpiece. And of course, don’t miss the chance to explore CMTM’s train exhibit in the Neighborhood. Put on your conductor’s hat, load up the luggage, and ring the bell as you immerse yourself in the world of trains. Train Day is Free With Admission.
Beer + Lobster Sail with Goodfire Brewing Co. + Portland Lobster Co. | Portland Schooner Co. | 5: 00 PM
Join Portland Schooner Co. for a Lobster + Beer Sail with two amazing partners—Goodfire Brewing Co. and Portland Lobster Co. Goodfire Brewing Co., known for their soft, unfiltered IPAs, will be aboard to sample some of their flagship beers as well as some of their new seasonal offerings while you sit back and enjoy one of “Maine’s Best Lobster Roll” from Portland Lobster Co. This two-hour special event sail will be hosted aboard Portland Schooner Co.’s Timberwind which sails from the Ocean Gateway Pier to the right of the Ocean Gateway building and across from the AC Hotel. Must be 21 years of age or older. Tickets.
For more events head to our Events Calendar here.