A Weekend Guide to Portland, Maine

Portland, ME Headlight

Portland, Maine, is the perfect destination for a New England weekend escape. Since Sam’s brother Joe and his wife, Kristen, moved there several years ago, we’ve been able to make two quick visits to the artsy coastal city.

Our most recent trip was in June, which was MUCH more pleasant than our first visit in February when the snowdrifts were literally above my head. I don’t think my toes thawed until mid March.

This time, the weather was perfect and we spent the entire weekend exploring the local restaurants, shops, and attractions. I had a fabulous time, despite the fact that I despise lobster (which is probably a criminal offense in Maine).

Here is our weekend guide to Portland, Maine:

 Where to Eat/Drink

 Tandem Coffee & Bakery

Tandem Coffee

For the best biscuit of your life, head to Tandem Coffee & Bakery on the West End. Located in a gas station turned Laundromat turned café, Tandem is the perfect breakfast spot.

In all seriousness, I don’t think a day has gone by since our trip that Sam hasn’t raved about the egg & cheese biscuit he ate there.

 742 Congress St, Portland, ME 04102

 Scratch Baking Co.

Scratch Baking Co

Scratch Baking Co. serves amazing bagels, which they make fresh daily. They also have a variety of tasty cream cheese spreads.

416 Preble St, South Portland, ME 04106

 FlatBread Company

Flatbread Company

For some seriously delicious wood-fired pizza, go to FlatBread Company. Not only is the food great, but its location on the harbor is one of the best in the city. If you’re visiting in the summer, sit on the patio and watch the boats go by.

72 Commercial St #5, Portland, ME 04101



Boda is open late and serves fantastic Thai street food. Because nothing says “vacation” like a late night meat skewer!

 671 Congress St, Portland, ME 04101

 Speckled Axe

Speckled Axe

If you’re in need of a caffeine fix, check out Speckled Axe, an artsy coffee shop serving a wide variety of coffee and teas.  

567 Congress St, Portland, ME 04101

 Where to Shop

 Longfellow Books

Longfellow Books

For my fellow book worms, be sure to check out Longfellow Books. It describes itself as a “fiercely independent community bookstore.” That really says it all.

1 Monument Way, Portland, ME 04101

 Yes Books

Yes Books

If you still haven’t gotten your fill of books, head to Yes Books. You could probably spend an entire weekend here and still not see everything, which is basically every book lover’s definition of paradise. If I had been traveling alone, this is probably where the list would end since I would still be camped out by one of its overstuffed shelves.

589 Congress St, Portland, ME 04101

Further Reading: Best Travel Books to Inspire Wanderlust


Find is a second-hand store in downtown Portland that sells trendy vintage clothing at good prices. Sam found an awesome pair of leather shoes here for $15.

16 Free Street, Portland, ME 04101


If you want to pick up a souvenir that’s not super tacky, check out Pinecone+Chickadee on Free Street. It sells an eclectic assortment of clothing, stationary, and gifts.

6 Free St, Portland, ME 04101

 What to Do

 Portland Headlight

Portland Headlight

No trip to Portland would be complete without paying a visit to the iconic Portland Headlight.  The view is absolutely beautiful.

 Bug Light Park

Bug Light Portland, ME

For some more lovely views, head to Bug Light Park. Trust me, the scenery is MUCH nicer than the name implies! We went at sunset.

 Farmer’s Market

Deering Oaks Farmers Market

If you happen to be visiting over a Saturday in the summer, check out the morning Farmer’s Market in Deering Oaks Park. Vendors sell everything from flowers to local produce to handmade pottery.

Our sister-in-law Kristen has her own pottery business called Campfire Studio, and she and Joe often have a booth set up in the Farmer’s Market. They are crazy talented, so you should definitely check out their work!

 Higgins Beach

Higgins Beach

Higgins Beach is the perfect spot for a day of relaxation. Spread out a beach towel and spend the afternoon dozing in the sand. Or, if you’re feeling adventurous, try your hand at surfing!

We rented our surfboards from the Black Point Surf Shop. We recommend springing for the wetsuits as well, since even in June the water can feel like glacial runoff.

To be honest, squeezing into the wetsuit probably gave me a better workout than surfing. It probably took longer too.

 Prouts Neck Cliff Walk

Prouts Neck Cliff Walk

The Cliff Walk is a lovely, mile-long hike along the rocky coastline. We did the hike in February, which turned out to be as good of an idea as the late-night meat skewers. The snow was up to my waist (see picture above for proof), and I think I almost died of hypothermia halfway through. It was basically a scene out of Everest. But in summer, this hike would be beautiful and not terribly strenuous.

 Ride the Mailboat

When visiting a coastal city, it’s always nice to get out on the water. For $16 you can hitch a ride on the Mailboat cruise. We haven’t tried this yet, but hope to on our next visit.

What is on your Portland bucket list?

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A Weekend Guide to Portland, Maine

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