Well, it is official. It’s the final weekend of summer and with just a few days left until we are greeted with fall’s arrival, you may have already felt the slight crisp of autumn’s air, seen your first sprinkling of pumpkin decorations, or thrown on your favorite cozy sweater for #sweaterweather. And while we warmly welcome the change of seasons, it wouldn’t be very Portland of us all if we didn’t send off summer with one last hoorah.
This weekend you can say goodbye to summer properly with the 1st Annual Big Deck Crawl, a Seagrass Strings Festival, an outdoor art + craft market, an end of summer bash at Fort Allen Park and more!
Here’s the Weekend Guide for Friday, September 16th – Sunday, September 18th, 2022!
Weekend Spotlight
Portland’s 1st Annual Big Deck Crawl | Multiple Locations | 2:00 PM – 8:00 PM 
If you like big decks and you cannot lie or you have B.D.E. (Big Deck Energy), then this is the event for you! Come wind down the summer on some of Portland’s best decks, including Thirsty Pig, Novare Res, The Porthole Amigos, and Bonfire Country Bar. Afternoon festivities will include drink specials, a “Guess-that-Deck” game with prizes, and an after-party at Citrus. This is a Choose Your Own Deck Adventure – check out any of the decks on the list for drink specials and find a “Guess-that-Deck” fact. All decks are within walking distance of each other. Tickets available here.
Friday the 16th
Negroni Week | ViA VECCHiA | Open All Weekend at 4:00 PM
Negroni Week is coming up and ViA VECCHiA is doing a Negroni Tour of The World to commemorate this iconic classic Italian cocktail. Beginning September 13th, the Negroni Passport will be available with different Negroni variations inspired by various parts of the World. For every cocktail, there will be an opportunity to get your passport stamped. Complete the tour to become a true Negroni aficionado. Proceeds from the passport goto the Negroni Week charity: Slow Food, a global movement of local communities and activists across more than 160 countries seeking to change the world through food and beverage.
East End Vend Outdoor Market | Austin Street Brewery | 3:00 PM – 7:00 PM 
East End Vend is a small and festive outdoor market for members of the Maine Crafts Association and non-members to participate as vendors alongside farmers and foodies. East End Vend markets offer a wide variety of art, craft, and other Maine products in a laid-back and community neighborhood setting.
Annual Book Sale | 1000 Riverside Street | 10:00 AM – 3:00 PM (Repeat Saturday)
Portland Public Library welcomes you back to the Annual Book Sale! This is a chance to benefit your public library and grab some great winter reads. There will be categories for Children, Youth, Cooking, Mystery, Science, Literature, Business, and more. Bring your friends, find some books, and feel free to make a generous donation to ensure everyone in the community can learn and discover at PPL.
Trash Blues Bash w/ Fat Knuckle Freddy | Amigos | 9:30 PM – 1:00 AM
Fat Knuckle Freddy’s annual Amigos patio gigs with BB Webber on drums. Psychobilly Trash Blues at its best. A duo that you will swear there’s a full band. Mark this show on your calendar and get ready to boogie to some Trash Blues.
The Kevin Midgley Players | Andy’s Old Port Pub | 8:00 PM – 11:00 PM 
The Kevin Midgley Players are back for a night of acoustic blues featuring national guitar, mandolin and harmonica at Andy’s Old Port Pub. Never know what else you might hear! Andy’s Old Port Pub is a casual pub frequented by locals from Casco Bay islanders and fishermen to business professionals and industry workers! 16 local craft beer lines, Honeymaker mead, and a full bar with several locally crafted spirits.
Saturday the 17th
Seeding Intention: A Morning Meditation Series | Urban Farm Fermentory | 10:30 AM – 11:30 AM
As an ancient technique rooted in Eastern culture and religion, meditation serves as a powerful tool for restoring balance to the mind, body, and nervous system. Seeding Intention is an integrative, 60-minute guided class that offers relaxation and contemplative practices drawn from both Eastern philosophy and modern evidence-based techniques. This blend allows meditators to explore the specific benefits for the individual mind and body. Tickets here.
Beautiful Blackbird Children’s Book Festival | Children’s Museum & Theatre of Maine | 9:30 AM -3:00 PM
The Children’s Museum & Theatre of Maine is proud to partner again with the Beautiful Blackbird Children’s Book Festival, a program that celebrates the voices, artistry, and impact of children’s literature created by and featuring Black people. The Museum & Theatre will present a robust in-person schedule of literary and art activities for the whole family, including Read Alouds featuring local community members and art-making workshops. In addition, the Museum & Theatre will offer a Pay What You Can ticketing option for all visitors to eliminate barriers families might face in taking full advantage of the new facility. Tickets here.
As part of the third annual Beautiful BlackBird Children’s Book Festival, you can also join Indigo Arts Alliance at their Cove Street location from 12pm – 3pm on Saturday for a panel conversation surrounding the past, present and future of the Black American Experience, inspired by the New York Times Magazine’s award-winning book “The 1619 Project: Born on the Water” by Nikole Hannah-Jones and Renee Watson. Event details here. This event is free.
Seagrass Strings Festival | Maine Craft Distilling | 1:00 PM – 9:00 PM
Seagrass Strings Festival is back for year two with a one-day bluegrass festival at Maine Craft Distilling featuring Grammy-nominated superstars Della Mae, beloved VA party-grass band Love Canon (playing acoustic versions of 80s pop songs), jazz-grass improvisors Mr Sun (featuring fiddle legend Darol Anger), west coast songster and picker Eli West, and the joyful upstart string-band Corner House. Fans of the mandolin will be happy to see Jake Joliff, Maddie Witler, Joe K. Walsh and Ethan Setiawan over the course of the day. Fiddle fans will be delighted by Darol Anger, Kimber Ludiker, Julian Pinelli, Isa Burke and Louise Bichan, and guitars fans can look forward to seeing Grant Gordy, Eli West, Jesse Harper, Avril Smith, and Ethan Hawkins. Tickets here.
Vivian’s House of Vice | Geno’s Rock Club | 8:30 PM – 12:00 AM 
Come up to the bawdy house of sinful delight! A night of class, sass, brass and absolute vice will surely do you right! House of Vice features premier burlesque, drag and variety acts from Maine and beyond.The house is on fire with these talented performers. Submerge yourself in the mischief and bring some loot for tipping! Jezebel Express (on tour to all 50 states! “she’s got all the curves and all the angles”), Moxie Sazzerac, Diamond DeVille, Raszzberry Beret, Creme Dela Phlegm, La Petite Mystique, Daisy Dee Mure and hosted by Clamz! Kasino. 21+ event and $15 at door.
Local Maker Pop-Up w/ Kriya Davis | Taproot Market | 11:00 AM – 4:00 PM
Taproot Market is hosting a pop-up with local jewelry maker Kriya Davis. Using traditional metalsmithing techniques, each piece of jewelry is crafted to possess a unique quality only found from hand worked metal. Focusing on simple, organic shapes along with texture and detail, she designs for those who value quality materials and thoughtful design. Find more at kriyadavis.com.
Sunday the 18th
Bellefest | Belleflower Brewing Co. | 12:00 PM – 7:00 PM
Belleflower Brewing Co.’s 2nd annual Bellefest event is here! This year they will be celebrating with not one, but TWO beer releases, including their first Dunkel, Gilded Meadow, and their fan-favorite Bellefest Lager! Will include visits from their friends at Jaju Pierogi and Rebel Cheesesteaks, along with live music from East Bayside Bluegrass Collective from 3-6pm, and a 
limited edition merch drop Wear your Bellefest long sleeve tee, get $2 off your first purchase and purchase a stein, get your first pour for $1!
Summer’s End Bash on The Eastern Promenade | Fort Allen Park | 4:00 PM – 9:00 PM
Bayside Music Company and Friends of the Eastern Promenade partner up to bring an evening of local music to Portland! Enjoy four performances from great local performers right on the bay, including Dark Rain, Assasi, and the Hippie Brothers Band. Hosted by the fabulous Chartreuse, this afternoon of music will be the summer’s end we all need.
Cryin’ Out Loud | The Porthole | 2:00 PM – 6:00 PM 
Cryin’ Out Loud is a super fun, high energy band that does a lot of up-beat blues and plenty of “classic rock.” They will be going live on The Porthole stage at 2 PM! Waterfront deck views and good times await.
Sanctuary Sunday | Flask Lounge | 9:00 PM – 1:00 AM
Come together for the best Sunday funday event at Flask Lounge, Portland’s one of a kind, neighborhood bar featuring live/local entertainment w/dj’s & bands of all genres. Bringing you a different theme each month, this month’s Sanctuary theme will empower multi genre EDM at its finest! Special DJ guest For the evening will be none other then, D Fuego, Kyle Minkler, who hails from Burlington VT. 21+ with ID. 5$ Cover.
Johnny Gandelsman: This is America | Cove Street Arts | 5:00 PM 
Co-founder of the adventurous string quartet Brooklyn Rider, Johnny Gandelsman has re-imagined the works of Bach, recording not only the complete violin sonatas and partitas, but also the complete cello suites, praised by the New York Times for “an improvisatory feel of folk music.” His new project, “This is America,” is a set of commissioned works for solo violin highlighting a diverse group of composers representing myriad genres and backgrounds. Tickets here.
For more events, head to our full Events Calendar here.
