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This weekend, love takes center stage! Love is in the air!
Whether you’re celebrating with a romantic evening or enjoying a night out with friends, Portland has plenty of exciting events to fill your weekend. Celebrate romance with sultry burlesque shows, lively dance parties, and heartwarming performances, or mix things up with a cozy wine pairing, a ski-themed celebration, or a funky Alice in Wonderland rave. Get ready to fall head over heels for these exciting events happening this weekend!
Please note that snow is predicted in the forecast for the weekend. We will do our best to post any changes / cancellations. Please be sure to check with each business/event before you head out!
Here’s the Weekend Guide for Friday, February 14th – Sunday, February 16th, 2025
Friday the 14th
The Red Eye Flight Crew: The Lonely Hearts Club Ball | Portland House of Music & Events | 9:00 PM
Whether you’re heartbroken, lovestruck, or just here for a good time, Gina Alibrio & The Red Eye Flight Crew’s Lonely Hearts Club Ball is the place to be this Valentine’s Day. Fronted by the powerhouse vocals of Gina Alibrio, this high-energy band will have you dancing the night away with soulful grooves, funky beats, and all the feel-good vibes you need. It’s a Valentine’s bash for everyone—couples, singles, and anyone who just wants to move. Leave the heartbreak at the door and hit the dance floor! 21+ only.
Black Hearts For Valentine’s Day Party | The End of Portland | 7:00 PM – 11:00 PM
Not feeling the roses and romance this year? The End of Portland has you covered with the Black Hearts for Valentine’s Day Party! This anti-Valentine’s bash is all about good drinks, great vibes, and zero heartbreak. Local print artist Jame Sylvester will be live-printing custom Black Heart Valentine’s cards—free for all the love cynics and independent spirits out there. Sip on mellow cocktails, fine spirits, or knock back a pint while embracing the dark side of the holiday.
Harlem Globetrotters | Cross Insurance Arena | 7:00 PM
The Harlem Globetrotters are back, and they’re bringing even more jaw-dropping trick shots, high-flying dunks, and next-level entertainment to the court! In their 2025 tour, they’re leveling up the game with new challenges, new moves, and the same mind-blowing magic fans love. Watch as they take on their longtime rivals, the Washington Generals, in a showdown packed with spins, slams, and show-stopping skills. Plus, with interactive fan moments throughout, you might even get in on the action!
Next Stop Comedy | Root Wild Kombucha | 7:00 PM
Next Stop Comedy is rolling into town and making a stop at Root Wild Kombucha, delivering big laughs with a fresh lineup of stand-up talent. Expect top-tier comedians—ones you’ve seen on TV and heard on your favorite podcasts—taking the stage at your go-to local spot. No two shows are the same, so buckle up for a night of unexpected hilarity!
Patent Leather Valentines Burlesque | Geno’s Rock Club | 9:00 PM
Celebrate Valentine’s Day in sultry style with a night of burlesque, showcasing local performers and special guests. Patent Leather is a tribute to playful pinups featuring plenty of lustrous leather, lace, stilettos, corsets, and leopard print. Whether you’re a fan of bold or demure, there will be something for everyone to enjoy—from cheeky garter belts to daring performances! Come dressed in your finest, whether you’re bringing a loved one or celebrating solo. Featuring: Cherry Glitterbomb, Siren Of The Circle, Cinnamon Maxxine, Vivian Vice, La Petite Mystique, and more! Hosted by Reverend Legs Malone, with kittens by Coral Ondaleft.
Galentine’s Day Workout & Wine Social with Burpees & Bordeaux | Blue Lobster Urban Winer | 6:30 PM
Besties who burpee together, stay together! Celebrate Galentine’s Day with a fun and energizing Workout and Wine Social with Burpees & Bordeaux workout class at Blue Lobster Urban Winery. A 45-minute all-levels workout class followed by a wine social! Your registration includes the class and one pour of wine, beer, or a non-alcoholic beverage of your choice (21+ for alcoholic beverages). After class, stick around for drinks and a relaxing hangout with your favorite gals! Don’t forget to bring your yoga mat and water bottle!
Saturday the 15th
February Break | The Children’s Museum & Theatre of Maine | 9:00 AM – 4:00 PM February 15th – 23rd
Looking for a way to keep the kids entertained during February break? The Children’s Museum & Theatre of Maine is your go-to spot for non-stop fun! Whether they’re climbing their way to the top in the indoor climber, getting lost in a live performance at Maddy’s Theatre, or meeting real ocean creatures, there’s something for everyone. Don’t miss the chance to help transform the museum’s iconic cow, Maggie, at MakerSpace. Check out the chalkboard for daily activity schedules, and let the kids unleash their creativity while you take a breather.
Bissell Brothers Basecamp | Bissell Brothers | 11:00 AM – 8:00 PM
Get ready to kick off ski season in style at Bissell Brothers Basecamp. It’s their annual day-long celebration, featuring the release of First Chair, Last Call, their trail-ready mountain ale. Bring your skis or board for a fresh wax courtesy of Wax on Wheels, and get the chance to mingle with friends from Saddleback Mountain and All Speed Cyclery And Snow. Enjoy a DJ set by Desert Wax, live acoustic tunes from Brad of Bradly Copper Kettle & Friends, raffles, cozy food specials, fire pits, ski movies on the big screen, and of course, a shotski to top it all off. Meet you at Basecamp!
Galentine’s Day | Smoked Portland | 11:00 AM – 5:00 PM
Gather your besties (and maybe your mini-me too) for the ultimate Galentine’s Day celebration at Smoked Portland! It’s all about friendship, fun, and fabulous jewelry at the Galentine’s Pop-Up Market. Enjoy cocktails, mocktails, and even a special drink for your little sidekick while you shop unique pieces from Weldology—bracelets, necklaces, charms, rings, and more. Plus, dine in and get 10% off your jewelry purchase because, hey, you deserve it!
LOVESICK, a Drag, Dance & Burlesque Valentine’s Bash | Austin Street Brewery | 7:00 PM – 11:00 PM
Get ready to get lovesick at Club 302’s after-Valentine’s bash! Whether you’re rocking the dance floor with your sweetheart or looking for love in all the right places, this night’s got it all—drag, burlesque, and the hottest beats in town! DJ SYD will be spinning slay-worthy tracks, while local legends Tasha Tektite and Ginjer Vitus serve up show-stopping drag performances. Plus, don’t miss a special burlesque act that will make the night even more unforgettable. So come through for a Valentine’s celebration you’ll never forget.
Galentine’s Day Party | Italian Heritage Center | 6:00 PM – 11:00 PM
Celebrate the love and laughter that comes with having an amazing group of gal pals! The Italian Heritage Center is hosting a Galentine’s Day Party that’s all about friendship, fun, and sweet surprises. This all-ages event promises music, raffles, tarot reading, selfies, delicious food, and an atmosphere full of good vibes. It’s the perfect way to honor the special bond of sisterhood and create unforgettable memories with your squad. Proceeds will benefit the local women’s shelter.
Tom DiMenna Sings Story Songs of the 70s | One Longfellow Square | 8:00 PM
Get ready to travel back in time with an unforgettable night of 70s storytelling through music. Tom DiMenna and his talented friends will breathe new life into the timeless songs of Cat Stevens, Gordon Lightfoot, and Harry Chapin, bringing their iconic story songs to the stage in this heartfelt tribute. With DiMenna’s powerful vocals and expert guitar skills, you’ll be transported straight to the golden age of singer-songwriters. Promises to be a true celebration of the legends!
Masquerave: An Alice In Wonderland Rave With The Hive | Shipyard Brewing Co. Tasting Room | 9:00 PM
Step down the rabbit hole and into a night full of magic, beats, and vibrant décor at this Alice in Wonderland-inspired rave. The Hive will be spinning electrifying EDM tracks, keeping the energy high and the dance floor buzzing. The Shipyard Tasting Room will transform into a whimsical wonderland, complete with interactive spaces and themed photo ops. Come in your best masquerade mask and costume to fully immerse yourself in the experience. Get lost in the fun!
Sunday the 16th![]()
Burlesque- Cover Moments and Mimosas | Novel | 1:00 PM – 4:30 PM
Step aside, candlelit dinners—this Valentine’s celebration is all about mimosas, romance, and a little bit of burlesque flair! Cover Moments and Mimosas with Blush & Bashful Burly at Novel – Portland’s book bar + café – invites you to sip, strike a pose, and step into your own romance novel cover shoot with the help of fabulous burlesque dancers. Afterward, mix, mingle, and settle in for a sultry, themed burlesque performance. Whether you’re bringing a date, your besties, or just treating yourself, this elegant daytime affair is sure to turn up the heat.
Greensky Bluegrass | State Theatre | 8:00 PM
Greensky Bluegrass isn’t just a band—they’re a force of nature. With two decades of high-energy performances, relentless touring, and a deep musical bond, these five road warriors have built a devoted following that packs out legendary venues like Red Rocks and The Ryman. Their sound blends traditional bluegrass roots with modern storytelling, delivering songs that hit right at the heart. Catch them live and see why their fans don’t just listen—they follow.
SHiNE Nation 10 Year Celebration! | Body Positive Dance Fitness | 11:15 AM
Body Positive Dance Fitness is celebrating 10 years of SHiNE with an all-request dance party! This one-of-a-kind class lets you pick the tracks, take the stage, and move to a mix of hip-hop, ballet, and jazz—all set to today’s hottest pop hits. Wear your shiniest outfit, bring your friends, and get ready to dance the day away in honor of a decade of feel-good, high-energy movement!
For more events head to our Events Calendar here.
