GET FESTIVE: BEST FESTIVALS IN STAYPINEAPPLE CITIES 2026
Photo by Gpointstudio via Canva
From the eclectic arts and indie music at Seattle's beloved Bumbershoot Arts & Music Festival at the Seattle Center, just a short walk from The Maxwell Hotel, to the soulful sounds of the Chicago Jazz Festival in Millennium Park, just a quick stroll from Staypineapple Chicago, there's plenty of festival fun waiting in our cities. Book your getaway, bring your appetite for adventure and make memories that last long after the festivities fade!
SEATTLE, WA
Blue Angels at Seafair Festival | Photo by Marco Bicca via Unsplash
Seafair Weekend Festival
When: July 31-August 2, 2026
Where: Genesee Park (20-min drive from The Maxwell Hotel and Hotel FIVE)
An annual Seattle tradition featuring Blue Angels air shows, hydroplane races, car shows, live music, food and family fun.
Brownies & Lemonade
When: August 1, 2026
Where: Fisher Pavilion at Seattle Center (10-min walk from The Maxwell Hotel, 15-min walk from Hotel FIVE, 15-min drive from Watertown Hotel & University Inn)
Under the shadow of the Space Needle, this high-energy festival brings together top EDM artists, immersive visuals, and an unforgettable night of dancing.
Bumbershoot Arts & Music Festival
When: September 5-6, 2026
Where: Seattle Center (2-min walk from The Maxwell Hotel, 15-min walk from Hotel FIVE, 15-min drive from Watertown Hotel & University Inn)
Over Labor Day weekend, the festival brings top music acts, immersive art, local food and creative experiences to Seattle Center.
Fremont Oktoberfest
When: September 18-20, 2026
Where: Fremont neighborhood (10-min drive from The Maxwell Hotel, Hotel FIVE, Watertown Hotel & University Inn)
Held in Seattle's eclectic Fremont neighborhood, this lively fall festival features local and German beers, live music, delicious food, and festive fun. Dogs are welcome on Sunday, so be sure to bring the whole pack!
PORTLAND, OR
Pickathon
When: May 23-June 8, 2025
Where: Pendarvis Farm (30-min drive from Hotel Rose)
Held just outside Portland, Pickathon is a beloved music festival featuring indie, folk, rock, and Americana artists, along with local food, drinks, and a scenic outdoor setting.
Mt. Angel Oktoberfest
When: September 17-20, 2026
Where: Mt. Angel, OR (50-min drive from Hotel Rose)
The largest folk festival in the Northwest, this event celebrates German heritage with traditional music, authentic food, craft beer, and family-friendly festivities.
SAN FRANCISCO, CA
Photo by Serigo Ruiz via Unsplash
Outside Lands
When: August 7-9, 2026
Where: Golden Gate Park (25-min drive from Staypineapple San Francisco)
The music festival features top headliners and a diverse lineup across genres, along with elevated food, wine, craft beer, cannabis and art experiences that highlight the best of the Bay Area.
Portola
When: September 26-27, 2026
Where: Pier 80 (20-min drive from Staypineapple San Francisco)
This music festival brings together top electronic, dance, and alternative artists for a high-energy weekend of music and waterfront views.
CHICAGO, IL
Millennium Park | Photo by Abel Arciniega via Choose Chicago
Lollapalooza
When: July 30-August 2, 2026
Where: Grant Park (5-min drive or 20-min walk from Staypineapple Chicago)
A legendary music festival, known for its diverse lineup of top global artists. Fans travel from around the world to be part of this high-energy celebration of music, art and culture.
Chicago Jazz Festival
When: September 3-6, 2026
Where: Millennium Park (5-min walk from Staypineapple Chicago)
This free celebration of jazz brings together world-class musicians, local artists, and a vibrant lineup of legendary and emerging talent.
NEW YORK, NY
Feast of San Gennaro
When: September 19, 2026
Where: Little Italy (25-min subway ride from Staypineapple New York)
This lively Italian street festival celebrates heritage with authentic cuisine, live entertainment, and family-friendly festivities, bringing the flavors and traditions of Italy to the heart of New York City
U.S. Open Fan Week
When: August 23-29, 2026
Where: Billie Jean King National Tennis Center (45-min subway ride from Staypineapple New York)
A major music festival featuring top artists across genres, with great food, art and high-energy performances.
BOSTON, MA
Boston Jazz Festival
When: August 28-29, 2026
Where: Maritime Park (15-min drive from Staypineapple Boston)
This vibrant celebration of jazz features talented musicians, live performances, and a lively atmosphere showcasing the rich sounds and culture of Boston’s music scene.
Boston Local Food Festival
When: September 20, 2026
Where: Rose Kennedy Greenway (15-min drive from Staypineapple Boston)
This celebration of local flavors brings together Boston’s best chefs, restaurants, and food makers for a delicious showcase of regional cuisine, drinks, and community.