Day 1 – Dive Bars & Giant Burgers
Forget the postcard seafood shacks—come here for retro beer bars where the jukebox fights with neon and the burgers are big enough to feel like a victory.
Allagash Brewing - Belgian beer made by Mainers who understand patience and yeast better than most people understand themselves. You come for the pours, stay for the smell of malt in the air, and leave just a little happier than you arrived. Try Shipyard Brewing as well if you can prioritize booze during your travels.
The Great Lost Bear (Oakdale) - A neighborhood beer shrine with 70 rotating taps, vintage ephemera on every wall, and legendary burgers like the Almighty Cheesus. This is where Mainers go to drink like they mean it.
Vientiane Market (Oakdale) - A Thai corner market that dispenses real-deal hometown curry and fiery Yum Nua, tucked into a grocery store nobody visits for the produce—but everyone visits for the food.
Portland Lobster Co. (Old Port) - Ok, who are we kidding? After a day of boozing, let Portland do what it does best - seafood. Know your environment, folks! Get to Harbor Fish Market or the Portland Lobster Co. for fish, simply done well.
Day 2 – All-Day Brunch & Duck-Fat Worship
If there’s one thing Portland perfects, it’s brunch—with a side of potato donuts or duck-fat fries that’ll make you rethink what “guilty pleasure” means.”
Land & Sea (Old Port) - Experience the historic waterfront district lined with cobblestone streets, local eateries, shops and an incredible harbor view. Then, get wet! Yeah, get out there on the water with a boat tour of the harbor. By the way, Coastal Maine Popcorn previously set-up shop in Old Port, but order it online when you get back home. Mix the Dill Pickle & Blue Cheese - it’s incredible!
Bayside American Café (Bayside) - A brunch institution that's not trying to be fancy—but has lobster omelets, chocolate waffles, and locals sitting elbow-to-elbow like it’s Sunday church.
The Holy Donut (Old Port) - Potato-based donuts with flavors like dark chocolate sea salt and maple bourbon bacon—a Portland staple that tastes like waking up and winning the day.
Duckfat (Old Port) - Fry anything twice-cooked in duck fat and call it elevated. Tuna melts that earned national praise, fries that defy logic, sandwiches that hit soul territory.
Day 3 – Elevated Plates & Local Craft
There’s all-day snacking here with a conscience—seafood that talks salt, tapas that whisper terroir, artistry in every poured drink.
Sur Lie (Munjoy Hill) - Small plates that speak of Maine farms and global riffs. Order the sweet-pea hummus and feel like spring is whispering back at you.
The Shop by Island Creek Oysters (East Bayside) - Oysters fresh from the water, no fuss, minimal menu, maximum marine personality. A slurp-and-go that rarely leaves you second-guessing.
Cong Tu Bot (Washington Ave) - A Vietnamese congee bar where chaó sò—clam porridge with sausage and mushrooms—is served under neon lights that overflow with weird charm and bold flavor.
Scales Restaurant (Old Port) - A working waterfront joint dressed up for dinner, but still with salt under its fingernails. Oysters that taste like the tide just rolled in, fish that still looks surprised to be on a plate.
Day 4 – Comfort Food & Hidden Community
This is where you find Maine’s kindness—healing veggie bowls, beef on toast, puppeteers and punks in an old church. It’s not curated, it’s just real.
Portland Museum of Arts (Arts District) - Forget the sterile white cubes of bigger cities—this place breathes. It’s small enough to feel human, big enough to surprise you. Local grit hangs next to world-class work, and somehow it all makes sense.
Green Elephant Vegetarian Bistro (Arts District) - A richly flavored vegetarian trip through Thai cooking, born from a chef’s mother’s hands. Even carnivores whisper about it for nostalgia of chili that bites back.
Empire Chinese Kitchen (Downtown) - Taipei-meets-Old-Port vibes—bold Chinese dishes that pack heat, heart, and unexpected loyalty from locals. This isn’t your average chop suey.
Mayo Street Arts (East Bayside) - A former church turned arts center—puppets, folk shows, neighborhoods’ untaught stories live here. A cultural refuge that feels like community in human form.