note 12: maine travel guide

A perfect weekend in Portland, Maine.

Apr 09, 2025

In the bag: Cape Cod chips, sandwiches + treats from Standard Baking.

Does everyone grow up with a complete angst for their hometown? I certainly did. But now that I’ve lived away from home for longer than I even lived there, I long for the days of my youth.

The coast of Maine. Lemonade stands. Camping on islands. Drives by the beach. Waitressing at the Fisherman’s Catch. Weekends with the “Portland boys”. It couldn’t have been all that bad… It was the quintessential childhood, but it took me leaving it all to appreciate it all.

I went back to visit the fam for my birthdayyyy (it was March 31!) and I had the perfect weekend. No drama. We did it! I’m also convinced that whenever I go home, I’ll run into people from high school—as if time stopped when I left and picks up again when I return. Not the case!

Here’s a recap of my favorite things to do if you ever find yourself in Vacationland.

15 things to do in Portland, Maine

STAY at the Longfellow Hotel. When I’m in Portland*, I usually crash at my sister’s (thanks, Molls) or at the AC Hotel downtown. Since it was my birthdayyyyy I wanted something special. Think boutique hotel with the bougie vibes. I saw this spot on a Vogue.com roundup and went for it. They have a spa and I booked a one-hour sauna suite for my Momma and me. Another perk is the town car that will take you downtown fo free. Loves it!
HAVE Breakfast at Miss Portland Diner—and ask to sit in the diner car. Get pancakes with Maine blueberries.

PICK UP donuts from The Holy Donut via the drive through. So yummy, and they have gluten-free options, too.
A matcha in my hotel bathrobe and snow outside? Paradise!
VISIT the Portland Museum of Art for a little culture. It was *the* date spot in high school. Or at least if you wanted to date me, that’s where you would take me.
RIDE the Casco Bay Lines ferry to one of the islands. Just be sure to respect the locals.
GO vintage shopping in the Old Port. If you’ve been following me since my Past Fashion Future days you already know I’m obsessed with secondhand, vintage, and thrift shopping. Visiting Material Objects is a Grady Girls ritual. We did it again with four out of the five Grady sisters.
We also hit up: Find, Weekend Vintage, and best of all: Open House, where I scoured a vintage suede bomber jacket. I had been searching for one on eBay to no avail and was so happy to find one IRL.
Open House, where I scoured the vintage jacket of my dreams.
GO for a cold plunge and sauna at Washington Baths. My sister and I went together on a previous trip and I didn’t know it was possible to feel that relaxed. Like if the fire alarm goes off I am not gonna be able to move type relaxed.
HIT UP LB Kitchen for lunch, brunch, a smoothie, or a matcha. When my sister lived in Munjoy Hill, I would walk here for my daily dose of health-centric meals. Everything is delish—and ya’ll know I love my gourmet cafés with New York prices.
GRAB Mexican takeout from El Rayo Taqueria. They have a few locations around Portland, and you can’t go wrong with their burrito bowls, plus chips + guac always.
Portland Head Light in the snow.
GO for a walk by the Portland Head Light. Proper Maine vibes, and a great photo op, too. On this day it was particularly windy and snowy, but oh-so pretty.
VISIT the L.L. Bean flagship in Freeport. It’s worth a visit at least once in your life. It made me think I might actually want to go camping. Like maybe there is a version of Emma who likes to explore the great outdoors, wear wool socks, sleep in a sleeping bag on the ground with a tummy full o’ baked beans and s’mores. Probably not though. I am still haunted from the camp days of my youth trying to find a “swim buddy” when I had no friends.
GO bowling at Bayside Bowl. It really brought out my competitive side.

GET a lobster roll from A Bite of Maine. Everyone asks me if I ate lobster all the time growing up as soon as they find out I am a Mainer. I sure didn’t. But it’s nice to have one every once in a while.
GRAB pastries from Standard Baking. Are you sensing a theme here?
HIT UP the Maine Mall. Just for old times sake. I went to Sephora to grab my free birthday gift and bought a blush that I promptly returned as soon as I got back to New York.
GO for a drive up the coast.
SPEND time with people you love. That was the main(e) focus of my trip after all. We stopped by my mom’s house in Kennebunk before hitting the road, and it was truly the best part. Feeling home. We don’t have the house I grew up in anymore, but Mom’s feels like home even if I've never lived there. Mason jars filled with beans and seeds. Her garden. Habitat for Humanity furniture. Wind chimes. Birds chirping. It’s a whole vibe.
BONUS: If you find yourself making the trip up from NYC, stop for lunch at Sally’s Apizza in New Haven, CT. Call ahead to order takeout or you’ll be waiting for at least an hour.

Emma, a.k.a., your favorite MAINEiac

EMMA GRADY

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