Between Pride, beer festivals, and some of the most popular “cons” (e.g., Comic Con), June is one of the best months to get out and enjoy what Staypineapple cities have to offer!

Top help you enjoy the fun, we’re excited to offer 25% off your reservation when you book for three or more nights! That’s plenty of time to find a new favorite brew, trot out multiple outfits, or get covered in glitter.


Beer tasting - June 8, 2019  (1 to 5pm)

A ticket to Brewshed Beer Fest gets you eight tasting tickets, with 18 breweries pouring at Hale’s Ales.

Comic Con - June 28 - 30, 2019

Ace Comic Con Seattle features actor guests, comic writers & artists, vendors & exhibitors, cosplay, and panel discussions at WaMu Theater & CenturyLink Event Center.

Pride Parade and festivals - June 29 - 30, 2019

PrideFest Capitol Hill is Saturday. Pride Parade starts at 11am Sunday at 4th & Union and ends near Seattle Center, site of Seattle PrideFest, the largest lesbian, gay, and transgender event in the Northwest. Free.


Festival of Flowers - June 1 - 4, 2019 (begin May 22)

See a giant design made from 20,000 flowers during Festival of Flowers in Pioneer Courthouse Square, with live music at noon on some days, followed by a flower sale.

Pride festival & parade - June 15 - 16, 2019

Portland Pride Festival includes food vendors and exhibitors both days at Tom McCall Waterfront Park. The free Portland Pride Parade begins 11am Sunday in the North Park Blocks and ends at the festival.

Beer & cider tasting - June 16, 2019 (1pm - 7pm)
A ticket to Snakebite Showdown allows you to taste six samples of beer and cider mixtures from 17 local producers at Widmer Brothers Pub for age 21+.

San Francisco

Beer festival - June 1, 2019

A ticket to San Francisco Beer & Music Festival gets you unlimited samples of 100 craft beers, with bands, DJs, and food for sale at Terra Gallery for ages 21+.

North Beach Festival - June 15 - 16, 2019

North Beach Festival features arts & crafts booths, food vendors, beer & wine gardens, entertainment, street painting, and a kids’ chalk area (cost) at Columbus & Grant Avenues. Free entry.

Pride celebration & parade - June 29 -30, 2019

Celebrate LGBT San Francisco Pride with performances and exhibitors at Civic Center Plaza both days, a giant Pride Parade Sunday at 10:30am on Market Street (from Beale to 8th), and a VIP Party at City Hall.

San Diego

San Diego Bay Festival - Jun 1, 2019

San Diego Bay Festival will take place at Embarcadero Marina Park North, June 1st and will be hosted by Music Box and DM events. The festival will run from 12-10pm with national headlining entertainment that is expected to draw 7,000+ attendees. San Diego Bay Festival gives attendees an opportunity to enjoy the first of San Diego’s summer sun. Delicious specialty foods, craft beers, craft cocktails, and fine wines will all presented by local restaurants, bars, and nightclub staff. Local arts and crafts, as well as booths, will be on sale throughout the festival.

San Diego Festival of the Arts - Jun 8 - Jun 9, 2019

Now in its 33rd year, the 2019 San Diego Festival of the Arts will continue this tradition, showcasing stunning works of painting, sculpture, photography, glass, jewelry, ceramics, wood, fiber and mixed media from nearly 200 world renowned artists June 8 and 9 at downtown San Diego's beautiful Waterfront Park. Ticket sales (starting at $14), a silent auction and wine and beer garden all contribute towards this philanthropic effort spearheaded by the Torrey Pines Kiwanis Foundation.

Father’s Day Cruises in San Diego  - Jun 16, 2019

Are you looking to spoil dad this coming Father’s Day? Make this Father’s Day in San Diego one to remember. Choose from a fun-filled beer brunch cruise or a sophisticated sunset dinner cruise. San Diego is known for it’s amazing climate so why not spend this Father’s Day outdoors with the whole family? Grab the sunglasses and make this San Diego Father’s Day unforgettable for Dad and the whole family!


Food truck fest - June 8 - 9, 2019 (noon to 10pm)

Pilsen Food Truck Social has dozens of food trucks, local restaurants, live music, craft vendors, and kids’ activities on 18th Street (from Racine to Throop). Donation.

Jazz at the aquarium - June 12 - Aug. 28, 2019

Hear musicians and vocalists, see views from the terrace, buy cocktails & food, and visit the aquarium at Jazzin’ at the Shedd at Shedd Aquarium.

Pride festival - June 22 - 23, 2019

Chicago Pride Fest is a huge weekend street festival for gay and lesbian pride with dance and pop music on three stages, plus vendors of food, drinks, and arts & crafts at Halsted Street & Waveland Avenue. The pet parade is Sunday at noon in the stage area. Donation.


Wine at the zoo - June 1, 2019 (5 to 7:30pm)

Sample wines at Roars and Pours [formerly called Uncorked] as you stroll past animals in the Tropical Forest Pavilion at Franklin Park Zoo for age 21+.

Beer tasting - June 2019 (undated)

Hosted by BeerAdvocate, Belgian Beer Festfeatures 100 Belgian styles and inspired offerings from 30 American and Belgian brewers, plus food for sale at the Cyclorama for age 21+.

Pride parade & festival - June 8, 2019

The highlight of LGBT Boston Pride Month is the Boston Pride Parade, which begins at noon in Copley Square and ends at Boston Pride Festival in City Hall Plaza. Free.

New York City

Music at Washington Square - June 4 - 25, 2019 (Tuesdays)

Washington Square Music Festival offers classical music in the park on Tuesdays, and occasionally jazz. Free.

Father’s Day restaurants - June 16, 2019

OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Father’s Day.

Pride Sunday - June 30, 2019

Pride Week events today include a noon Pride March down 5th Avenue and then up 7th Avenue (route map), an afternoon PrideFest street fair, and Pride Island at Pier 97, typically followed by fireworks.

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