Eating and Drinking Our Way Through the City in 24 Hours
Introduction: What happens when you and your friends decide to flip the script on typical 24-hour Portland guides and challenge yourselves to eat and drink your way through the city for a full 24 hours? You get “The Portland 24” – a food and drink marathon like no other. It all started as a joke, but soon turned into one of the craziest and most fun challenges we’ve ever done. In this blog post, we’re breaking down our entire journey, from planning the stops to the amazing food and characters we encountered along the way.
The Challenge: We wanted to see if it was possible to eat and drink something at 24 different locations in Portland over the course of 24 hours. This meant mapping out restaurants, cafés, bars, and even late-night diners that would keep us fueled and going strong all day and night. The logistics were no joke, but every restaurant we visited was incredible to work with, making the challenge that much more enjoyable.
Our Stops: Here’s the full list of the 24 places we visited during The Portland 24 challenge, starting at 4 AM and ending our last stop at 3 AM the next day:
- Becky’s Diner 4am– The iconic start of our journey at 4:00 AM with classic breakfast fare.
- Tony’s Donuts 5am– Old Portland staple known for its blueberry glazed doughnuts.
- Hi-Fi Donuts 6am– Monument Square’s new-school donut spot with deep-fried goodness.
- Barista & Bites 6:30am– (Bonus stop) Grabbing a quick coffee and pastry.
- Coffee Me Up 7am– Strawberry cheesecake pastries paired with cold brew.
- Bayside American Cafe 8am– Classic brunch spot with mimosas and Eggs Florentine.
- The Front Room 9am– Wings, pickleback shots, and Narragansett beers.
- The Eastern Prom 9:45am– Rest Stop
- Terlingua 10am– Latin American BBQ joint with killer brisket and breakfast tacos.
- The Honey Paw 11am– Asian-fusion dishes, including lobster toast and fried chicken.
- Tomaso’s Canteen 12noon– Wings, pickleback shots, and Narragansett beers.
- Gritty McDuff’s 1pm– Portland’s original brewpub for English-style ales.
- Mami 2pm– Serving up Japanese street food from their new brick-and-mortar spot.
- Portland Hunt and Alpine Club 3pm– Iconic cocktail bar where we took things up a notch.
- The Thirsty Pig 4pm– Live music, sausages, and great local beer.
- The Grill Room 5pm– Delicious steaks and a relaxed atmosphere to recharge.
- Solo Italiano 6pm– Incredible Italian fare, including octopus and lightly fried sage leaves.
- Highroller Lobster Co. 7pm– Lobster tacos and lobster grilled cheese to keep the momentum going.
- Portland Lobster Company 8pm– Lobster rolls, steamers, and a true Maine experience.
- Sur Lie 9pm– Farm-to-table dining with a stellar cocktail and wine list.
- Eventide Oyster Co. 10pm– Brown butter lobster rolls and some of Portland’s best seafood.
- Gross Confection Bar 11pm– Dessert-forward cocktails paired with unique sweets like goat cheese ice cream.
- Blyth & Burrows 12midnight– Nautical-themed cocktails in one of Portland’s top cocktail bars.
- Bill’s Pizza 1am– Late-night pizza that tastes like victory after 22 hours of eating and drinking.
- PT’s (Strip Club) 2am– A detour from the planned stop, adding a bit of adventure to the night.
- Denny’s 3am– The only place still open at 3:00 AM to end our challenge with a Moon’s Over My Hammy.
Memorable Moments: Along the way, we met some colorful characters and had some unforgettable experiences. Whether it was chatting with locals at a cozy pub or enjoying the signature dishes at each stop, the challenge turned into a real exploration of Portland’s diverse food scene.
The Final Stop: After 24 hours of non-stop eating and drinking, we wrapped up the challenge at Denny’s at 3am. Exhausted but satisfied, we couldn’t believe we had pulled it off. Every location brought something unique to the table (literally), and we left with full stomachs and plenty of great memories.
Final Thoughts: If you’ve ever wondered whether you could eat your way through Portland in 24 hours, we’ve got the answer – it’s possible, but you’ll need a solid plan, a great team of friends, and a strong appetite. We hope you enjoy watching the video of our adventure as much as we enjoyed living it. Have you ever tried something like this? Let us know in the comments!
Conclusion: “The Portland 24” wasn’t just a food challenge – it was a celebration of Portland’s incredible culinary scene and the amazing people who make it all possible. Be sure to check out the full video on our YouTube channel to see the adventure unfold!