Rose City Caddy

Rose City Caddy Big Black 1958 Cadillac Fleetwood Sixty Special

11/14/2025

Make your Christmas lights tour one to remember! Rose City Caddy is offering exclusive holiday rides in a gorgeous 1958 Cadillac, gliding you through Portland’s brightest displays.
• Skip the wait with a VIP fast-pass
• Enjoy easy downtown pickup/drop-off (expanded service available)
• Add a little holiday rock ’n’ roll and upgrade to an Elvis-driven tour!

Wishing you the Happiest Halloween from Rose City Caddy!
10/31/2025

Wishing you the Happiest Halloween from Rose City Caddy!

Best seat in the house after delivering the bride for her amazing day. Congrats to Amanda and Ross!
10/05/2025

Best seat in the house after delivering the bride for her amazing day. Congrats to Amanda and Ross!

Congrats to Amanda and Cory on this perfect, still summer, evening!
09/21/2025

Congrats to Amanda and Cory on this perfect, still summer, evening!

Congrats to Jolie and Tazio on this beautiful Sunday evening!
08/04/2025

Congrats to Jolie and Tazio on this beautiful Sunday evening!

Congrats to Delaney and Sander on this perfect Saturday!
07/20/2025

Congrats to Delaney and Sander on this perfect Saturday!

Just another beautiful Saturday evening out celebrating another happy couple. Congratulations to Heather and Richard.
07/06/2025

Just another beautiful Saturday evening out celebrating another happy couple. Congratulations to Heather and Richard.

Congrats to Sara and Tom on this magical Friday!
06/14/2025

Congrats to Sara and Tom on this magical Friday!

Huge congratulations to Luke and Alexis on tying the knot in timeless style.
06/08/2025

Huge congratulations to Luke and Alexis on tying the knot in timeless style.

An absolutely perfect evening to celebrate Sara and Clarence on their amazing day.
05/25/2025

An absolutely perfect evening to celebrate Sara and Clarence on their amazing day.

Big upgrade alert for the Caddy!Since I do a lot of wedding drives after dark, I've been thinking for a while about impr...
05/19/2025

Big upgrade alert for the Caddy!

Since I do a lot of wedding drives after dark, I've been thinking for a while about improving the headlights. The old halogens did the job, but let’s just say… they weren’t exactly lighting up the night.

Over the weekend, I installed a full set of Holley RetroBright LED headlights — and wow, what a difference! Not only do they look sharp, but they’re also DOT legal and fit perfectly in the original buckets (which aren’t exactly roomy to begin with).

This weekend will be the first big outing with the new lights and I’m pretty excited to hit the road after sunset. Let there be (vintage-correct) light!

Address

711 NE Dekum St
Portland, OR
97211

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