By Lily Ray Wyss, June 25, 2025
Because nothing says “I live here now” like a themed group ride and a mid-ride coffee stop.
Whether you’re new to Portland or just finally dusting off your two-wheeler, community bike rides are one of the best ways to get outside, explore the city, and meet people who understand why it’s totally normal to talk about tire pressure over brunch.
Here are some local favorites to check out:
Pedalpalooza (Summer-long Bike Festival)
Dozens of rides daily, all summer long
Want to ride your bike dressed like a disco ball? Or cruise along to Beyoncé’s greatest hits with a pack of strangers-turned-friends? Pedalpalooza is the Portland summer bike culture experience. It’s 3 months of DIY, themed group rides hosted by locals — everything from chill sunset rides to costumed pub crawls.
Location rotates by neighborhood, May–September
Totally free, totally fun, and designed for everyone — this family-friendly event shuts down miles of city streets so you can bike (or scoot, skate, walk, stroller-push) through some of Portland’s most beloved neighborhoods. Food carts, music, and local vendors at every stop? Yes please.
Usually hosted out of local breweries like Ecliptic or Hopworks
If your idea of cardio includes a post-ride pint, you’re in the right place. These casual group rides pair scenic routes with good beer — plus you usually get a pint glass and other swag. Cheers to that.
Night Ride (by the Street Trust)
One magical evening every summer
Glow sticks, neon everything, and a sea of lit-up bikes cruising through Portland after dark. It’s festive, it’s sparkly, and yes — it’s family-friendly too. Come for the vibes, stay for the post-ride dance party.
Slow Poke Rides (or WTFNB Rides)
Great for new riders or anyone who hates racing vibes
These are super inclusive rides often hosted by and for women, trans, femme, and nonbinary folks (but not exclusively). Chill pace, affirming energy, and no judgment if your brakes squeak a little.
Where to Find Even More Rides
If you want to find a themed ride literally any day of the week:
Shift2Bikes.org Calendar – the best one-stop-shop for spontaneous group rides.
Instagram hashtags: #pedalpalooza #bikefunpdx #portlandbikeride
Local bike shops: Sellwood Cycle Repair, Gladys Bikes, and Clever Cycles often post events on their bulletin boards or IG.
See you out there Portland!
Check out my Instagram @Lilyrayresidential for more fun things to do around Portland.
Lily Ray Wyss
Broker | OR
She/Her
I love Portland. This city, and its surrounding areas, in my opinion, are the perfect place to call home. We have the amazing ability to put our toes in the ocean, snowboard, and visit some of the world's best breweries all in one day. Our food scene is extremely diverse and prolific. Want to see a show? Comedy, music, theater, etc all have growing, well-supported scenes here. I love selling homes in Portland and more importantly educating my clients and community on how amazing this city is and how you can own a piece of this beautiful state and call it home.
Follow me on Instagram to see my new finds and spotlights on the best places to eat, play, and be entertained in the area. And for information on buying/selling and current home market data. Follow at: @lilyrayresidential
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- T: 971-361-6114
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