As we creep closer to Halloween, Portland is lighting up with spooky fun and fall festivities!
This weekend is packed with eerie excitement, from the All Hallows’ Market to the spine-tingling Walk Among the Shadows Cemetery Tour and Portland Ballet’s Thrills and Chills performance. For those who want to enjoy the season’s magic in a different light, don’t miss the enchanting Portland Lantern Walk or the family-friendly Harvest Fest. Let’s dig in!
Here’s The Weekend Guide for Friday, October 18th – Sunday, October 20th, 2024
Friday the 18th
Walk Among the Shadows | Eastern Cemetery | Repeats thru the 20th + 24th – 27th; Thursday thru Saturday, 6:30 PM + Sunday, 5:30 PM
Walk Among the Shadows: The Portland Rum Riot of 1855 brings Portland’s history to life in the most chilling way. This immersive tour through the Eastern Cemetery takes you back to a time when Mayor Neal Dow’s push for Prohibition sparked outrage among Portland’s working class, leading to the infamous Rum Riot. You’ll encounter characters from both sides of the conflict, from bootleggers to temperance supporters, and even Dow himself. Hear their stories and witness how a clash over alcohol turned deadly, changing the city forever. It’s a perfect blend of history, protest, and Halloween spirit! Tickets.
Northeast Sports Card Expo | Portland Expo | 9:00 AM – 4:00 PM (Repeats Saturday)
The Northeast Sports Card Expo returns to Portland taking over the Portland Exposition Building. With over 200 vendor tables across 24,000 square feet, you’ll find everything from vintage sports cards to Pokémon cards, collectibles, and more. Celebrity autograph guests include former Boston Bruins, New England Patriots players, and professional women’s hockey stars, with a free autograph from each guest included in admission. Expect on-site card grading, prize raffles, and fun for the whole family! Tickets.
Primal Soup (Phish Tribute) | Bayside Bowl | 8:00 PM
Get ready for an unforgettable night with Primal Soup, New England’s premier Phish tribute band! Join them for a live performance that dives deep into Phish’s signature blend of intricate compositions and exploratory jams. Established in late 2023, Primal Soup has already built a devoted following and is known for delivering authentic, high-energy shows. Show is all-ages! Tickets.
Little Lies: A Tribute to Fleetwood Mac | Portland House of Music | 8:00 PM
Little Lies: A Tribute to Fleetwood Mac brings the magic of one of the world’s most iconic bands to life with an 8-piece ensemble from Boston. Featuring two male and two female vocalists, this tribute band delivers all your favorite Fleetwood Mac hits with authenticity and energy. Get ready for a night full of romance, drama, and the timeless sounds of Rumours. Little Lies promises the essence of Fleetwood Mac. Tickets.
Saturday the 19th
Crafts, Crepes and Creeps | Coveside Coffee | 9:00 AM – 1:00 PM
Swing by for Coveside Coffee’s final mini-market of the year and enjoy tasty treats from Crepe Elizabeth while browsing unique crafts from talented local makers like Allison Mckeen, Ellie Begin, Liz Mgee (@estraith), Rose Acolyte Ceramics, and Weave and Sow. Coveside will be open from 8 AM, and while part of the lot will be reserved for vendors, there’s plenty of street parking available. Don’t miss out on this perfect fall Saturday outing!
Fresh Pressed Harvest Fest | Freedom’s Edge Cider | 12:00 PM – 8:00 PM
Autumn is here, and so is the Fresh Pressed Harvest Fest at Freedom’s Edge Cider in Portland’s East Bayside neighborhood! A must-attend festival for cider lovers and those looking to celebrate the bountiful flavors of the season, this exciting event promises a day full of delicious cider, lively entertainment, fun contests, local makers, live apple pressing, raffles, apple Olympics, food trucks, sunset toast, and more. Read on.
Smoked’toberfest | Smoked Portland | 3:00 PM – 7:00 PM
Get ready for the 1st annual Smoked’toberfest at Smoked Portland! This local BBQ joint is hosting a day packed with fun games where you can win awesome swag and Smoked Gift Cards. The weather is shaping up to be perfect, and Kelly Towle – Co Host of The Blake Show with Kelly & Todd – will be the fabulous Master of Ceremonies, sporting her best German-inspired costume. Expect stein racing, barrel rolling, beer stein hoisting, bratwurst swinging, and so much more!
Halloween Boobtacular | Geno’s Rock Club | 8:00 PM – 11:00 PM
Join Geno’s Rock Club and Vivian Vice for a night of fabulous fun at the Halloween Boobtacular! Get ready to celebrate both boobs and boos with a thrilling lineup of supernatural burlesque and drag performances! Prepare to be dazzled by the glamorous ghouls, featuring stars like Creme Dela Phlegm, La Petite Mystique, Cherry Glitter Bomb, Sarah Tonin, Bunny Belvedere, Luna Lee, Carmina, Page Turner, and Riot Romero. Plus, show off your creativity in the costume contest for a chance to win exciting prizes! Tickets.
Portland Lantern Walk | Deering Oaks Park | 5:00 PM
Join for the Portland Lantern Walk, an annual celebration of community, culture, and creativity in Deering Oaks Park! This enchanting event invites participants to craft and carry their own lanterns, transforming the park into a breathtaking spectacle of light. Blending tradition with innovation, the Lantern Walk showcases the talents of local artists, musicians, and performers, enriching Portland’s landscape. Fun for the whole family!
Primary Dance Night Halloween Party | Flask Lounge | 8:00 PM
Join at Flask Lounge for a thrilling night as they celebrate 10 years of Primary and Doomsday’s 20th year DJing! Dive into the dark and danceable sounds of your favorite post-punk, synthpop, and new wave spooky tunes with DJs Zimbra, Dirty Keys, and Doomsday. Costumes are encouraged, so bring your A-game for a chance to shine on the dance floor! This 21+ event is just $5 before 10 PM and $10 after.
Portland Ballet’s Thrills and Chills Sneak Peek | Children’s Museum & Theatre of Maine | 11:00 AM – 11:30 AM
Join Portland Ballet for a special sneak peek of their family-friendly Halloween-inspired ballet, featuring talented students from the Senior and Pre-Professional Divisions! This enchanting performance blends Halloween-inspired dances with eerie classical music, creating a delightful experience that’s just spooky enough for audiences of all ages. Admission includes access to this captivating showcase, held in Maddy’s Theatre on the first floor. Be sure to check the chalkboard upon arrival for a complete list of times and activities, so you don’t miss a moment of the fun! Plan your visit.
Sunday the 20th
Bodega After Hours: PJs + Papi Halloween | Papi | 7:00 PM
Get ready for the ultimate Bodega Culture pop-up experience at Papi! Dive into a night filled with delicious snacks and expertly crafted cocktails, all while soaking in the vibrant atmosphere that celebrates the essence of NYC’s iconic bodegas. Pull up in your comfiest pajamas and relive those late-night bodega run complete with special food and drink offerings available night long. Secure your place for this unforgettable evening on Resy.
Bob The Drag Queen This Is Wild World Tour | State Theatre | 7:00 PM
Fresh off emceeing Madonna’s The Celebration Tour, comedian and drag superstar Bob The Drag Queen is ready to captivate audiences with his first headline comedy world tour. As the winner of season 8 of RuPaul’s Drag Race, Bob has since garnered accolades, including a Peabody Award and GLAAD Media Award, for his work on HBO’s We’re Here. This 18+ event promises a dynamic blend of stand-up comedy, crowd work, and music, showcasing Bob’s unique flair and charisma. An unforgettable night that dives deep into the heart of what makes Bob a true entertainment icon! Tickets.
All Hallows’ Market | Congress Square Park | 11:00 AM – 3:00 PM
The All Hallows’ Market returns to Congress Square Park for another eerie and exciting celebration! Get into the Halloween spirit with locally made treats, spooky art, and plenty of themed goodies. Play horror-inspired games with Another Round, and keep an eye out for a surprise special guest! The market features an incredible lineup of vendors like Spun Bakery, Plot Twist Pretzels, Art By Abbeth, SuperMutz Dog Bakery, and many more. Whether you’re looking for unique crafts or just want to soak up the Halloween vibes, this market is the perfect way to kick off the spooky season!
Alex Lopez and The Xpress and Memphis Lighting | The Hill Arts | 7:00 PM
Get ready for a night of electrifying blues-rock as Alex Lopez and The Xpress team up with Memphis Lightning at The Hill Arts for the Lightning Xpress Tour! These two nationally touring artists will each deliver their own powerful sets before joining forces on stage for an unforgettable performance of classic rock and blues. Alex Lopez, a Billboard-charting artist known for his captivating guitar work and vibrant blend of blues, rock, and funk, will showcase hits from his seven albums, including the acclaimed Looking for a Change. Memphis Lightning, led by guitar virtuoso Lightning Thiboutot, is renowned for its high-energy, dynamic performances that fuse influences from Danny Gatton to Mick Jagger. Don’t miss this unique show that’s been lighting up stages across the country! Tickets.
For more events head to our Events Calendar here.