While many people consider August the end of the summer season, summer doesn’t officially call it quits until September 22nd. And if you ask us, that still leaves plenty of time to soak up the sunshine and fun before we swap swimsuits for sweaters.
Whether you’re clinging to those last beach days or simply not ready to let go of summer’s energy, these events will keep the good vibes rolling. From outdoor music festivals to markets and lobster roll cruises, here are 10+ perfect ways to hold onto that summer feeling just a little longer.
Keep the summer vibes alive with Reggae Sunday at Camp Pennant! Zion Train will be providing the summer spirit a little while longer with their infectious island tunes and beats.
And it’s not just the music—Camp Pennant’s aesthetic adds to the summer magic. Think nostalgic Maine summers with camp-outs and seaside adventures, all wrapped up in rustic Vacationland charm. Pull up to the full-length bar with views of the distillery and soak up those lingering summer views!
When: Every Sunday from 2pm – 5pm
As summer begins its graceful exit, keep the good times rolling with Summer Sunsets at Thompson’s Point. This weekly Thursday and Friday evening event is your go-to for soaking up the last of the season’s sunshine.
Enjoy an evening filled with live music, award-winning food trucks, and crafted cocktails, all while taking in the best sunset views Portland has to offer. With free admission, it’s the perfect outing for everyone— local, visitor, or somewhere in between. Pet-friendly and kid-friendly, it’s also an all-inclusive, good-vibes-only gathering where you can bring friends, family, or co-workers to enjoy the sunset together.
When: Starts at 4pm Thursday, August 29th, September 5th, September 12th; Friday, September 13th
As we hold onto the last drops of summer, make your Labor Day weekend shine at the Fête Market. Hosted at Austin Street Brewery, this outdoor market is a treasure trove of local creativity, featuring everything from stunning illustrations and unique jewelry to innovative designs and handcrafted goodies.
Sip on a cold brew and stroll and browse unique gifts, all while you enjoy the summer vibes on the brewery’s sunny patio. It’s the perfect way to savor the season’s warmth and creativity before autumn’s arrival!
When: Saturday, August 31st from 1pm – 6:30pm
Dive into summer vibes with the ultimate island escape at Crown Jewel’s Tiki Takeover – the grand finale of the season!
Join for a tropical celebration with the country’s premiere tiki bar, Three Dots and A Dash. This Windy City legend is bringing their legendary rum cocktails and island vibes to Portland’s trendy cocktail oasis on Great Diamond Island. It’s one of the last chances to soak up those permanent vacation and island vibes before the last day of service on Sunday, September 15th. Come ready to sip on expertly crafted tropical cocktails while enjoying the best of tiki flair.
When: Saturday, August 31st from 3pm – 10pm
Summer vibes continue to roll on with the Lobster Roll Cruise on Casco Bay, hosted by Fogg’s Water Taxi!
Hop aboard the historic Joseph S. Kennedy for a scenic journey through the bay, where you can indulge in fresh Maine lobster rolls from Island Lobster Company on Peaks Island. This cruise is the ultimate summer experience, blending breathtaking coastal views with Maine’s most iconic cuisine. Sip on local beverages available for purchase onboard, and soak in the last days of summer in true Maine style.
When: Saturday, August 31st and September 7th; Sunday, September 1st and September 8th from 12pm – 2pm
Mix up your summer sun with some serenity! This September, join the Wellness in the Park Series with Health Resonates, where you can connect with nature and your well-being. Whether you’re into yoga, sound healing meditation, pilates, or just want to enjoy a moment of peace, this series offers a perfect way to hold onto those summer vibes while nurturing your body and mind!
Set in Fort Sumner Park, this is a great opportunity to recharge and rejuvenate before fall arrives. Not to mention, each class is FREE!
When: 9am – 10am Saturday, September 7th, 14th, 21st, and 28th
Nothing says summer like an unforgettable wine sail through Casco Bay, courtesy of Wine Wise!
Join Sommelier Erica Archer aboard the beautiful Frances, a 74-foot sailboat, for an educational and scenic journey as you explore five exquisite Mediterranean wines. From Greece to Italy, and Spain to Lebanon, on this particular sail you’ll get a taste of the region’s best reds while learning about the unique characteristics that make them shine. Pair your wine with a delightful selection of cheeses, cured meats, and more, and enjoy the stunning views of Maine’s lighthouses and islands.
Tickets for the Mediterranean wine sail. Wine Wise offers a selection of wine sails to choose from including French Reds, Pidemont, Italian Reds, Oregon and Washington and more.
When: Sunday, September 8th from 3:30pm – 5:30pm
Summer’s not over yet, and there’s no better place to hold onto those warm vibes than on The Porthole’s legendary big deck! On Sunday, September 8th, catch live music from local favorites Chase Jobe & The Running Kind bringing their electrifying country vibes to the waterfront.
As Portland’s go-to spot for summer fun, The Porthole is where you can soak up the last rays of the season, surrounded by great tunes, good company, and the vibrant energy that defines “The Way Portland Does Summer.”
The Porthole will be rockin’ live music on the deck into September. Be sure to check out their live music calendar for the full line-up.
When: Sunday, September 8th at 6pm
Ahoy, smooth sailing into September! Keep the summer vibes going strong at The Portland Yacht Rock Festival at Aura, where local musicians will bring you the best of smooth classics from TOTO, America, Bread, Steely Dan, and more. It’s the perfect way to hold on to those sunny, carefree days as we sail toward fall!
This annual celebration of yacht rock tunes will have you cruising through a sea of nostalgia with laid-back grooves and timeless hits. Come aboard for an evening of easy-listening favorites that perfectly capture the spirit of summer.
When: Friday, September 13th starting at 8pm
As summer lingers, keep the sunny vibes in rotation at the 4th Annual SeaGrass Music Festival at Maine Craft Distilling! Celebrate the season’s final notes with an afternoon of live music, delicious food, and refreshing drinks.
Doors open at 2pm, and the music kicks off at 3:30pm with: Haggard and Cashed (featuring Erica Brown + Matt Shipman); Mr. Sun (with Darol Anger, Joe K. Walsh, Grant Gordy, and Aidan O’Donnell); Brittany Haas (joined by Yann Falquet + Mr. Sun); and Cahaba Roots (featuring some Berklee all-stars)
Grab your tickets and enjoy a day of family-friendly fun with your little ones (kids under 12 get in free) and furry friends (outside only).
When: Sunday, September 15th from 2pm – 10pm
Celebrate the last of summer evenings with the September Third Thursdays at the Portland Museum of Art!
During the summer months, this year-round event spills out onto the Shaw Family Sculpture Park, where you can enjoy live music, food trucks, and interactive art under the stars. This month, explore the Peggy Bacon: Biting never Bitter exhibition, enjoy portrait drawings with Josie Colt of Portraits as You Pass, and grab some tasty bites from Black Tie and Cheese the Day! It’s a fantastic way to make the most of the final few days of summer.
Free entry all day into the museum and complimentary parking from 5pm – 8pm in the MaineHealth parking lot.
When: Thursday, September 19th 10am – 8pm free access to the museum but evening party usually starts around 5pm
Wrap up the summer vibes with Gina & the Red Eye Flight Crew on the Bayside Bowl rooftop!
This all-ages soirée features Boston-based vocalist Gina Alibrio, whose powerful vocals and catchy songwriting blend blues, funk, and R&B. Joined by members of Rustic Overtones, Jaw Gems, Sister Sparrow & the Dirty Birds, and Model Airplane, this nine-piece band delivers an electrifying mix of pop, soul, and R&B that’s sure to keep you dancing. Bound to be a memorable evening as we close out summer!
When: Thursday, September 19th
Still holding onto that summer energy? Portland Bike Party is here to help you ride (and dance) it out!
Join “The Hottest Club in Portland” for their September ride, where bikes meet beats as you cruise around the city, stopping for dance breaks at some of Portland’s most fun spots. Dress up in your flashiest gear, pedal to the rhythm, and let the good times roll—this free, monthly bike/dance party happens year-round, but there’s no better time to join than while those summer nights are still warm!
LOCATION: STILL TBA
When: Friday, September 20th
Looking for more? Be sure to check out our Events Calendar for events happening in Portland, Maine – includes live music, happy hours, markets, shows, and more!
