With Cinco de Mayo AND the Kentucky Derby this weekend is lining up to be one festive one! Are you ready?
The weekend ahead includes vibrant Cinco de Mayo fiestas, thrilling Kentucky Derby watch parties, a rebellious Punk Rock Prom, and a joyful Children’s Book Week. And if that’s not enough, on Sunday we embrace the spirit of community as Sundays on the Boulevard returns to Back Cove!
Here’s The Weekend Guide for Friday, May 3rd – Sunday, May 5th, 2024
Friday the 3rd
Hard Deck Opening | The Porthole | All Weekend
Kick off Summer 2024 in style at The Porthole! Starting Friday, May 3rd, join them for a hard launch into the season with live music by Chase Jobe & The Runnin’ Kind at 6 PM. Then, on Saturday, May 4th, don your fascinators and dapper attire for their Kentucky Derby Watch Party! Enjoy live music by The Cover Tones at 2 PM and Sugarbox at 6 PM. On Cinco de Mayo, groove to the tunes of Doubting Gravity at 2 PM. Throughout the weekend, indulge in drink specials, including a frozen treat featuring Owen’s Mixers Classic Lemonade. Don’t miss out on the second annual Summer Kickoff Extravaganza – only at The Porthole!
Punk Rock Prom | Geno’s Rock Club | 8:00 PM
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Get ready to unleash your inner rebel at Punk Rock Prom – where you can wear whatever the f*ck you want! The party kicks off at 8 PM with performances by Scotty Saints – Melodic skate punk from the mean streets of Maine; El Grande – Portland’s longest running ska band; The Lazy Anarchists, and Bad Idea USA. A night of punk rock mayhem!
FoCSP Season Kickoff | Congress Square Park | 6:00 PM – 7:30 PM
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Join Friends of Congress Square Park as they kick off the 2024 season of free programming at Congress Square Park! They’re thrilled to welcome friends from Taiko Maine Dojo, a community taiko drumming group from right here in Portland, for an unforgettable performance. Plus, groove to the beats of the Ideal Maine Social Aid & Sanctuary Band, and indulge in delicious treats from the Totally Awesome Vegan Food Truck.
Angels In America Pt. 1: Millennium Approaches | Portland Stage | May 1 – May 26th – Multiple Times
Embark on a journey through the heart of America’s cultural landscape! Witness the intertwining lives of six New Yorkers amidst the tumult of the AIDS crisis, as Louis abandons his lover, Prior becomes a prophet, and Harper ventures to Antarctica. Directed by Keith Powell Beyland & Peter Brown, and featuring a talented cast including Joseph Bearor, Paul Haley, and Michela Micalizio, this Pulitzer Prize-winning masterpiece delves deep into themes of politics, spirituality, and sexuality with sharp humor and profound insight. Presented in partnership with Portland Stage, it’s a theatrical experience showcasing the resilience of the human spirit even in the darkest of times. Tickets.
Dub Apocalypse ft. Dana Colley of Morphine/Vapors of Morphine | Sun Tiki Studios | 7:00 PM
Experience the mesmerizing sounds of Dub Apocalypse, an instrumental dub reggae band hailing from Boston. With a fusion of influences including Sly and Robbie, Scientist productions, and the explosive energy of Coltrane-inspired saxophone, Dub Apocalypse creates a unique musical tapestry that captivates audiences worldwide. Featuring current and former members of acclaimed bands such as John Brown’s Body, The Skatalites, and Morphine, Dub Apocalypse brings decades of combined experience to the stage, delivering soul-shaking performances at clubs, theaters, and festivals across the globe. Experience the soul-shaking throw down of a Dub Apocalypse live show. Tickets.
Jordan Klepper Suffering Fools | State Theatre | 6:00 PM Doors
Jordan Klepper is a household name, celebrated for his incisive commentary on the political landscape. Known for his work on The Daily Show and Emmy-nominated specials, Klepper fearlessly delves into the heart of contentious issues. Klepper’s versatility extends beyond television, as he co-hosts podcasts like StarTalk with Neil deGrasse Tyson and explores conspiracy theories in the Webby award-winning “Fingers The Conspiracy.” With appearances across CNN, MSNBC, and various comedy platforms, Klepper continues to leave an indelible mark on both comedy and political discourse. Tickets.
Children’s Book Week | Children’s Museum & Theatre of Maine | May 2nd – May 8th
Step into the enchanting world of storytelling during Children’s Book Week at CMTM, which features daily pop-up story times, special guest appearances by real children’s book authorsand more. Explore the artistry behind the books with Art for Tots sessions highlighting the work of illustrators, and unleash your creativity in the MakerSpace with a week-long Make-Your-Own-Book takeover. It’s a celebration of reading and creativity! All activities are included with admission, so be sure to check the chalkboard upon arrival for activity times and schedule. Tickets.
Saturday the 4th
Spring Margarita Class Hosted by The Roaming Speakeasy | Toad& Co. | 4:00 PM – 7:00 PM
Indulge in the spirit of spring with The Roaming Speakeasy! Join Toad& Co. for a Cinco de Mayo-inspired cocktail making class and learn to craft the perfect margaritas. You’ll be guided by a skilled bartender to make a classic and a spicy pineapple jalapeno margarita. Your ticket includes all tools, ingredients, and garnishes, plus light snacks to complement the margs. Dive deep into the art & science of mixology as you’re guided through crafting these flavorful libations. The class will be an hour and additional drinks will be available for purchase to keep the celebration going. Class is open to adults 21 years of age or older. Proper ID is required. Tickets.
Kentucky Derby Watch Party | Rigby Yard | 5:00 PM
Join for Rigby Yard’s Annual Kentucky Derby Watch Party in partnership with Maker’s Mark! Immerse yourself in the excitement of the Live Derby action while enjoying classic Mint Juleps and delectable Hot Brown Sandwiches. Plus, don’t miss out on thrilling gifts, photo opportunities, and exciting prizes throughout the day. Dress to impress in your finest derby attire for a chance to win best dressed honors! Reserve.
Kentucky Derby Annual Party | Dock Fore | 12:00 PM
Start your Derby Day celebrations early at Dock Fore with Arsenal vs Spurs kicking off at 7:30 AM. Then, join Dock Fore for the Derby Party starting at 3 PM, featuring $1.95 PBR or High Life pints until the end of the race. Savor authentic Mint Juleps and don’t forget to flaunt your best hat for a chance to win a fabulous prize. A day of excitement and festivities!
Our full rundown of Kentucky Derby Watch Parties + Events in Portland, Maine
Maifest | Belleflower Brewing Co. | 12:00 PM – 8:00 PM
Join Belleflower Brewing Co. in East Bayside for a traditional German celebration welcoming the arrival of spring. And guess what? A little birdy say that they’ll be unveiling a new beer release too! Save the date and get ready to indulge in delicious fare from Ironclad Eats and Lady Shuckers. Plus, groove to the beats of Singer/songwriter Grace Marie and Marshall.
Straight No Chaser: The Yacht Rock Tour | The Merrill Auditorium | 7:30 PM
Straight No Chaser returns for one night only! Dig out your deck shoes: RIAA-certified Gold a cappella group Straight No Chaser will set sail on “The Yacht Rock Tour,” sparking sing-alongs to classic 80’s songs of summer. If the phrase “male a cappella group” conjures up an image of students in blue blazers, ties, and khakis singing traditional college songs on ivied campuses… think again. Straight No Chaser are neither strait-laced nor straight-faced, but neither are they vaudeville-style kitsch. They have emerged as a phenomenon with a massive fanbase and a long list of accomplishments including 2 RIAA Gold Certified albums, over 1.5 million concert tickets sold, over 1 billion streams on Pandora, and over 2 million albums sold worldwide. Tickets.
Sunday the 5th
Fiesta! Cinco de Mayo | Terrarium | 11:00 AM
Spice up your Cinco de Mayo! Join on the El Rayo Portland patio from 1-4pm for live music by Party Time Excellent, setting the perfect backdrop for your celebration. Indulge in drink specials, beer buckets, mouthwatering food specials, giveaways, and even Jell-O Shots! Rain or shine, the party is on, so grab your amigos and join us for a Cinco de Mayo fiesta to remember at El Rayo!
Our full rundown of Cinco de Mayo Celebrations and Specials in Portland, Maine.
Sundays on the Boulevard | Back Cove | 9:00 AM – 4:00 PM
Get ready to reclaim the streets and embrace the outdoors as Sundays on the Boulevard returns! Beginning on Sunday, May 5 Baxter Boulevard will transform into a pedestrian paradise, welcoming walkers, bikers, and play enthusiasts alike. From 9 AM to 4 PM every Sunday, enjoy the freedom of car-free streets and soak up the fresh air and sunshine. Presented by the City of Portland, this year’s Sundays on the Boulevard promises to be a season-long celebration of community and outdoor recreation, running through Sunday, September 29, 2024.
American Idol Watch Party | Canopy Hotel | 8:00 PM
Maine pride on full display! Join at Salt Yard Cafe + Bar inside Portland’s Canopy Hotel as they rally behind Maine’s very own Julia Gagnon on the big screen for American Idol! Show your hometown support in style! Drink specials will be offered during the watch party.
Primal Movement with Sara Kunz | Botanically Curious | 10:30 AM
Join at Botanically Curious for an invigorating hour of movement and release with Sara Kunz, renowned wellness coach and survivalist. With a knack for helping individuals overcome obstacles and embrace life’s adventures, Sara draws upon her expertise gained from appearances on Discovery Channel’s ‘Naked and Afraid’. Using mind-body practices and the wisdom of nature, Sara guides participants to connect with their authentic selves and cultivate joyful resilience. Bring your own mat (BYOM)! Tickets.
Caravan Artisan Market | Allagash Brewing Co. | 11:00 AM – 4:00 PM
Join Allagsh Brewing Co. as they unlock The Cellars to host Caravan Artist Market, a curated list of incredible artisans. 30+ vendors will be outside on the patio and inside lining the walls of beautiful barrels of rare brews. Find the highest quality of artists and makers around, selling unique original art, paintings, prints, photography, pottery, illustration, stationary, clothing, toys, jewelry, accessories, skin care, candles, homewares and more! Shop and treat yo’self with rare beers, wine, cider, and other beverages, beautiful barrel scenes, and good vibes—this will be one week out from Mother’s Day, after all. The Bite Into Maine food truck will be serving up tasty food including some festive taco offerings from the patio, and ArtVan will also be joining with a free activity for the kiddos.
For more events head to our Events Calendar here.