Madison: Trolley Pub Crawl Downtown with BYOB & Guide

4.75

(128 reviews)

What’s the experience like?

We were already laughing before we even left the curb, trying to sync up our pedaling on this big green trolley thing in downtown Madison. Our guide—Shawn, I think?—cracked a joke about “leg day” and handed us the aux cord, so someone put on Prince (not my pick, but it worked). The first few blocks felt like being in a parade, people waving or shouting out from the sidewalk. I could smell pizza somewhere nearby—maybe wishful thinking since we’d skipped lunch.

The first bar stop was on Regent Street. Inside, it was loud but friendly—bartender called out Trolley Pub deals before we even sat down. Four White Claws for $14, plus nachos or pizza if you wanted to split. We went for the nachos, which were messier than I expected but hit the spot after all that pedaling. I tried to order in my best Wisconsin accent and failed miserably; bartender just grinned and poured another round. Back outside, the air felt cooler against my sweaty shirt and you could hear the Capitol’s bells faintly over our playlist.

Later, rolling along John Nolen Drive (I think?), Shawn pointed out where Lake Mendota opens up behind the Capitol dome. We stopped for those $3 Trolley Shots—no idea what was in mine but it tasted like summer camp lemonade spiked with something stronger—and a boozy slushie that made my tongue numb. There was this moment where everything just slowed down: sunset turning the lake orange, everyone quiet for a second except some geese honking somewhere nearby. I still think about that view sometimes when I’m stuck at work.

By the time we finished our last stretch of pedaling (harder than it looks after two hours), nobody cared who was steering straight or singing off-key. The city lights came on as we rolled back toward where we started. Not sure if it was the beer or just Madison being Madison, but I left feeling lighter than when I arrived.