Let’s get this out of the way: Portland doesn’t need another top 10 list. Google "things to do in Portland, Maine" and you’ll get a hundred versions of the same safe answers—eat a lobster roll, visit the lighthouse, walk around the Old Port. They’re not wrong. But they’re also not the full picture.
This isn’t that kind of list.
This is the list I’d text a friend who’s visiting for the weekend. The kind of friend who’s already seen the postcards and wants to know what’s actually good—what locals do when they’re not playing tour guide. No fluff, no filler. Just my favorite spots, moments, and habits in this weird, wonderful little city.
Start with coffee. Always.
Double Great Cappachino
Tandem Coffee + Bakery (West End & Bayside): Two locations—one for slightly better coffee, one for marginally better food—but the Bakery wins out. A cortado and a breakfast sandwich that makes your day before 9am.
Another Round Café (Congress Street): , Game Cafe , and criminally good coffee. (Great for working)
Double Great Coffee (Deering Center): Bright, cozy, and full of people who actually care about what’s in your cup. ( No laptops allowed)
Second Rodeo (South Portland): The best bang-for-your-buck breakfast sandwich in Greater Portland, full stop.
Bard Coffee (Old Port): A Portland coffee institution.
Smalls (West End): Coffee, Bites and Mini Market
Take a walk that isn’t the Old Port.
Looking at Back Cove
Western Prom + Western Cemetery: The quiet loop I do when I need to clear my head. History, trees, space to breathe.
Eastern Prom: Still gorgeous. Still underrated in the mornings.
Back Cove Trail: Especially during golden hour. Seagulls, salt air, and long views.
Congress Street on First Fridays: The most alive this city gets. Art, weirdos, energy. Walk slow.
Eat like you live here.
Wayside Tavern: Every time i go it never disappoints.
The Great Lost Bear: A Portland classic, but the wings are still undefeated.
Ocatillo: Bold flavors, warm space—go with someone who loves to share.
Pai Men Miyake: Ramen and Katsudon that punch above their price.
Do something weird.
SPACE Gallery: Experimental art, indie films, music that might make you question your entire taste.
Geno’s Rock Club: Especially on drag night—rowdy, real, and always memorable.
Argenta Brewing Run Club: Even if you don’t run, it’s a good hang. Beer + community wins.
Portland’s Gallery Scene: Try stopping into Roux and Cyr, Cove Street Arts, and the Portland Art Gallery, or pick a random gallery in the old port, chances are good it’ll surprise you.
Shop where the good stuff is hiding.
Viand Mercantile
Blanche + Mimi: Thoughtful, layered, romantic home goods. $$$
Strata: For anyone who appreciates tools, knives, and function. $$$
Post Supply : Vintage Inspired , curated, and Beautiful $$$
Viand Mercantile: Antiques mixed with Modern home goods $$
Open House: Antique store, beautifully curated $
Moody Vintage : Vinyls and Clothing. $
Grab a drink somewhere
Taco Escobar: Legit margaritas and the best kind of chaos.
Ruskis: Locals only. Portland at its most unfiltered.
Bramhall: Candlelit, subterranean, and just a little haunted.
Lincoln’s: Cash only. Speakeasy,
CBG: Always a good call. Solid food, solid drinks, and no pretense.
Blyth & Burrows: Some of the best cocktails in Portland Maine
Lucky Cheetah: When you want cocktails with bite and atmosphere to match.
Longfellow Hotel Bar: Quiet, classy, unexpectedly great.
Get outside the downtown bubble
Maker’s Market
Thompson’s Point: Food trucks, roller skating, concerts, a cider bar, and probably someone on a unicycle. Never miss the Maker’s Market.
South Portland Greenbelt: Ride your bike and feel the coast in your lungs. One of the best ways to see the working side of the waterfront.
Don’t forget the in-between.
You’ve got a list now—but Portland isn’t just about ticking boxes. It’s about the stuff that happens in the middle.
Like walking your dog through Deering Oaks Park right before sunset, when the light gets soft and the city slows down a little. Or the way strangers say good morning on the greenway path like it’s second nature. You notice those things here.
It’s grabbing a coffee and ending up in a conversation you didn’t expect. It’s hopping the ferry to Peaks Island and realizing the best part isn’t the view, it’s that salty air, the quiet hum of the engine, and knowing a slice of Il Leone pizza is waiting for you.
The best parts of this place don’t always make the brochures. They’re small moments that stay with you.
