May is when Seattle finally wakes up.
The clouds back off (mostly), the flowers explode, rooftops open, and locals crawl out of hibernation like they’ve never seen daylight. It’s not just the weather — it’s the vibe. The energy. The feeling that this city is finally, officially alive again.
If you’re planning a trip, just moved here, or thinking about staying longer, this is the best month to fall in love with Seattle.
Here’s everything you need to know about Seattle in May — what to expect, what to do, where to go, and why you might not want to leave.
What to Expect in May
Seattle isn’t hot yet — and that’s part of the charm.
Temps: Mid-50s to high 60s (ideal layering weather)
Rain: Still shows up, but more like an occasional guest than a problem
Sunsets: 8:30 PM and climbing
Vibe: Patios fill up, ferry lines get longer, and everyone’s suddenly nice again
It’s also one of the least touristy months to visit. You get all the beauty, none of the crowds.
Wander Azalea Way in Bloom
You want your Seattle spring moment? This is it.
Azalea Way is where the entire city comes to breathe again — a long, quiet path framed by towering trees and wild color.
What to expect:
Rhododendrons, dogwoods, and cherry trees in full bloom
Lush moss-covered benches and shaded trails
Ducks, birds, maybe even a bald eagle if you’re lucky
What to do:
Walk the full ¾ mile slowly. You’ll want to stop every few minutes.
Pack a book or lunch — there are so many perfect spots to sit.
Visit the nearby Japanese Garden for the calmest 45 minutes of your life.
Why it matters: This isn’t a park. It’s a reset button.
Kayak Through the Middle of the City
Imagine paddling past million-dollar houseboats while a seaplane takes off overhead and the skyline floats in front of you. It sounds fake — but it’s real. And you can do it in a T-shirt.
Best beginner route (90 min loop):
Launch at Agua Verde or Moss Bay
Paddle west toward Gas Works Park
Loop around the floating homes in Portage Bay
Return past the UW shoreline
What you’ll see:
The “Sleepless in Seattle” houseboat
Dogs on paddleboards
Tech bros in electric boats pretending they’re outdoorsy
What to bring:
Dry bag (you’ll thank us)
Snack or sandwich
Sunglasses with a strap — the water reflects hard
Bonus: Rent an electric boat instead and cruise with a speaker + charcuterie.
U District Street Fair (May 18–19)
This isn’t your average “walk around and browse” fair. It’s 200+ vendors, live music, people dancing in the street, grilled meat smells in the air, and a whole lot of chaotic good energy.
What to expect:
Art, crafts, handmade clothes, vintage tees
Food you didn’t know you wanted until you smelled it (birria tacos, skewers, Korean corndogs, yes)
People playing drums. Children doing flips. Possibly a dog in sunglasses.
What to do:
Bring cash. Some vendors won’t take cards.
Plan to spend at least 2 hours wandering
Find a shady curb, eat something fried, and people-watch like it’s a sport
Sunday at Fremont Market
If Ballard’s the polished brunch crowd, Fremont is the cool cousin who thrifted their outfit and knows how to haggle. Every Sunday, it’s a rotating mix of food, vintage, art, and surprises.
What you’ll find:
Retro jackets, mid-century lamps, random cassette tapes
Mini donuts, tamales, pho, and espresso martinis in to-go cups
Street musicians, chalk art, and someone selling beaded mushroom earrings
What to do:
Start with coffee at Milstead & Co.
Browse the vendors you think “aren’t your style” — that’s where you’ll buy something
Walk to Theo Chocolate after and grab truffle samples
Rooftop Season Has Officially Started
Seattle rooftops don’t mess around — and now that the weather’s warming up, the views (and the drinks) are on point.
We’ve actually got a whole separate blog post breaking down our favorite rooftops across the city — from low-key breweries to bougie skyline bars.
🔗 Read it here: Seattle’s Rooftop Season Is Officially Open
Loop Discovery Park and Watch the Sun Go Down
If there’s one trail that convinces people to move here, it’s this one.
Discovery Park is 534 acres of forest, cliffs, beaches, and trails — and it’s inside city limits.
What to expect:
2.8-mile loop trail
Bluff views over Puget Sound
A secret beach where people write things in driftwood
What to do:
Hike the main loop before sunset
Detour down to the lighthouse
Bring snacks. Sit. Watch the sky turn gold.
Why it matters: It’s the city’s best kept natural escape — and no two visits feel the same.
Ride the Bainbridge Ferry
One of the easiest, cheapest, and most beautiful things you can do in Seattle — even if you don’t leave the boat.
What you’ll see:
The entire skyline behind you
Puget Sound spread out like glass
The Olympic Mountains, if you’re lucky
If you hop off:
Get coffee and a pastry at Blackbird Bakery
Browse Eagle Harbor Books
Walk along the waterfront or rent a bike
Pro tip: Time your return trip with sunset. It’s a movie.
Catch a Film at the Seattle International Film Festival (May 15–25)
The Seattle International Film Festival takes over theaters across the city — showing global cinema, under-the-radar gems, and the kind of movies you’ll be recommending for the next year.
What to expect:
Screenings at SIFF Uptown, Egyptian, Northwest Film Forum, and more
Documentaries, world premieres, shorts, and experimental films
People dressed in full festival fits, talking about French cinema in line
What to do:
Book your screenings early — seats go fast
Hit SIFF Lounge for drinks between showings
See something you’ve never heard of — that’s the point
Connect with Michael Haas for a free consultation: Book Here
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