GET FESTIVE: BEST FESTIVALS IN STAYPINEAPPLE CITIES
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
Seattle International Film Festival
When: May 15-25, 2025
Where: Venues across Seattle including:
SIFF Cinema Uptown (10-min walk from The Maxwell Hotel)
SIFF Cinema Downtown (3-min walk from Hotel FIVE)
Held across multiple venues, the festival showcases over 100 independent and international films. When you come to celebrate the magic of film, save on your stay with promo code FESTIVAL and make your SIFF experience even more cinematic!
When: July 19, 2025
Where: University District (participating shops within short walking distance from Watertown Hotel & University Inn)
Celebrate the U District as the bubble tea capital of the Northwest, featuring tasty flavors and bubble tea-inspired treats in the heart of boba culture.
When: August 1-3, 2025
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.
Bumbershoot Arts & Music Festival
When: August 30-31, 2025
Where: Seattle Center (2-min walk from The Maxwell Hotel)
Over Labor Day weekend, the festival brings top music acts, immersive art, local food and creative experiences to Seattle Center.
PORTLAND, OR
Portland Waterfront Blues Festival | Photo by NASHCO Photo via Travel Portland
When: May 23-June 8, 2025
Where: Tom McCall Waterfront Park (across the street from Hotel Rose)
During the festival, the park hosts CityFair – a lively carnival with rides, live music, food and vendors. The Grand Floral and Starlight Parade routes run nearby, offering easy access to enjoy the festivities.
When: July 4-5, 2025
Where: Tom McCall Waterfront Park (across the street from Hotel Rose)
A fun summer event featuring incredible live music, delicious food and drinks, and a spectacular Fourth of July fireworks show over the Willamette River.
When: July 4-6, 2025
Where: Elizabeth Caruthers Park (7-min drive from Hotel Rose)
A big outdoor party showcasing the widest selection of local beers, ciders, and wine-based cocktails – all crafted in Portland.
Project Pabst
When: July 26-27, 2025
Where: Tom McCall Waterfront Park (across the street from Hotel Rose)
A 21+ music festival created by the famous Pabst Brewing Company, features an exciting mix of well-known and emerging artists.
San Francisco, CA
Photo by Sergio Ruiz via Unsplash
Carnaval San Francisco Festival
When: May 24-25, 2025
Where: Mission District (30-min drive from Staypineapple San Francisco)
The free festival is part of Carnaval – a celebration of the diverse Latin American, Caribbean and African Diasporic roots of the Mission District and Bay Area. It spans 17 blocks and features international food, dancing, tasting spots and entertainment.
When: May 31-June 1, 2025
Where: Union Street to Fillmore to Gough Streets (15-min drive from Staypineapple San Francisco)
The festival brings neighbors and visitors together to celebrate local culture with live music, dance, food, craft beers, cocktails, arts and crafts, and family-friendly games – including the fun Waiter Relay Race.
When: August 8-10, 2025
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.
San Diego, CA
Wonderfront Festival | Photo by Alan Hess via San Diego Tourism Authority
Wonderfront Music & Arts Festival
When: May 16-18, 2025
Where: Entrance at Ruocco Park (5-min drive from Hotel Z)
The high-energy festival is spread across multiple stages and features artists from hip-hop and EDM to indie rock and soul – plus local food, craft beer, art installations and yacht parties.
When: August 30-31, 2025
Where: Gallagher Square at Petco Park (5-min walk from Hotel Z)
The festival is a celebration of island and reggae music, bringing people together through rhythm, culture and community vibes.
When: October 17-19, 2025
Where: Mission Beach at Mariner’s Point Park (20-min drive from Hotel Z)
A legacy music festival set against the scenic waterfront, featuring top-tier artists, local food and craft drinks.
Chicago, IL
Millennium Park | Photo by Abel Arciniega via Choose Chicago
When: June 5-8, 2025
Where: Millennium Park (5-min walk from Staypineapple Chicago)
The largest free blues festival in the world, which celebrates the city’s legendary blues scene with the genre’s most revered musicians, along with up-and-coming and local talent.
When: June 7-8, 2025
Where: Huntington Bank Pavilion at Northerly Island (15-min drive from Staypineapple Chicago)
The popular electronic music festival features top DJs, immersive themed stages, art and a wonderland-inspired atmosphere.
When: July 31-August 3, 2025
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.
new york, ny
Harlem Week | Photo by Michelle Rick via NYC Tourism + Conventions
When: June 4-15, 2025
Where: Various venues (most under a 30-min subway ride from Staypineapple New York)
A premier celebration of independent film, featuring screenings, panels and events that spotlight emerging voices and world-class storytelling.
When: June 6-8, 2025
Where: Flushing Meadows Corona Park (30-min drive or 40-min subway ride from Staypineapple New York)
A major music festival featuring top artists across genres, with great food, art and high-energy performances.
When: August 1-17, 2025
Where: Various venues across Harlem (25-min subway ride from Staypineapple New York)
An annual celebration that showcases the rich history and culture of Harlem, highlighting its African-American, African, Caribbean, Hispanic and European roots through arts, music, business and community events.
Boston, ma
Boston Calling | Photo by Kyle Klein via Meet Boston
When: May 23-25, 2025
Where: Harvard Athletic Complex (15-min drive from Staypineapple Boston)
A popular music festival featuring major live acts across multiple stages, plus visual arts, food and a 100-foot ferris wheel.
When: July 2-4, 2025
Where: Various locations along waterfront and downtown Boston (10-min walk to Back Bay Station to take Green Line, with festival locations accessible via multiple stops on this route)
A family-friendly festival honoring the city’s maritime and revolutionary heritage.
When: September 6-7, 2025
Where: Christopher Columbus Park (12-min drive from Staypineapple Boston)
Celebrating local visual and performing artists, this free waterfront festival features live music and artist booths.
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