Copy My Trip: 3 days in Portland, Maine

13.09.2024 - 09:13 / lonelyplanet.com

Sep 12, 2024 • 6 min read

Lonely Planet’s senior social media manager, Rachel Lewis, recently returned from a weekend with her wife in Portland, Maine. Here she shares her trip highlights and what to prepare for before you go.

I’ve always had a clear picture in my head of what visiting Portland, Maine would be like, and, honestly, it was pretty stereotypical: buttery lobster, stripes and linen, setting sail from the Old Port and thumbing through pottery at local shops. I’d never been to Maine, period, but when I told my grandmother (who’s from Massachusetts) that I was planning a long-weekend trip with my wife, she had two recommendations: eat as much as you can manage, and go to the locally owned Cool As A Moose (and buy her a mug for Christmas – on it, Gramma). My wife and I landed with empty tums and space in our luggage for goodies, and hit it. 

I want to help you do the same. Here are a few things that made my weekend in Portland so memorable.

The Longfellow Hotel in the West End is a newly opened boutique hotel with a heart for sustainability. On our first morning in Portland, we tested out room service with a breakfast order of an iced oat milk latte. I got just what I was craving, and my wife couldn’t stop raving over her breakfast sandwich – baked egg, spicy mayo and pepper jack on an English muffin.

I was particularly impressed with the creative mocktail menu at its dinner and drinks venue, Five of Clubs. Finding good alcohol-free drinks when traveling sober (or sober curious, in my case) can be tricky, but the “functional cocktails” are stunning. I had a Rosarium – bitter orange, earl grey, pomegranate – and a Vacationland Refresher – wild Maine blueberry, cardamom, lemon soda. The earl grey was a great intro to the -ber months. 

The spa, Astraea, has an infrared sauna (reserve it in advance!), and you can get your very own space with a bathroom, rain shower and sauna. There are a few different massage options. We chose Mindful Dreams, a meditative, rhythmic full body massage ($145/person for 60 minutes). Sip peppermint tea and feel wonderful as you lounge about in your new skin (okay, I know that’s not how it works, but it’s how it feels).

I'm not even going to attempt to single out a "best" meal in Portland, but with its foodie reputation, you can expect to dine well. These are the dishes, snacks and flavors that stood out for us.

Brickyard Hollow Brewing Company is a local chain that makes gourmet pizza from Freeport to Yarmouth (the original) and beyond. We went with cheese pizza, and it was beautiful in its simplicity: 12 inches of cheesy goodness with an olive oil base. Next time, though, I’d grab something more experimental, like its blueberry pizza with Maine blueberries, rosemary