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A Weekend for 30-Somethings in Portland, Maine: Rooftop bars, Breweries and Biking

By January 14, 2022April 14th, 20225 Comments

Sara did a near-perfect job covering Portland, Maine, with a great list of things to do and eat. But if you fall in love with this city like we did, you’ll want a few different options, right?! So when my husband and friends visited recently, we came up with a whole new itinerary option for a weekend full of bougie cocktails, strong brews and lots of outdoor time.

Finding drivable spots in New England is perfect to while away the winter weekends. So let’s see what’s up with Portland — less than two hours away by car.

Friday: Check in downtown and hit happy hour

Canopy by Hilton

canopy hilton in portland maine

This brand-new property right the old part of town. It’s extremely walkable and a wonderfully luxurious option, with several suite options that offer a bright, sunny space. Not to mention, the new Luna Rooftop Bar is already the place to gather in Portland on the top of the hotel. Choose a fun drink inspired by Greek goddesses, paired with some tapa-style plates and desserts.

The Portland Hunt + Alpine Club

alpine club portland maine

With hearty food options, we opted out to save room for the rest of the evening, but we couldn’t help trying the Swedish meatballs. Obviously, it was much better than Ikea!

Blyth & Burrows

blyth and burrow portland cocktails oysters

We definitely got our mojo back as new parents at this chic watering hole. I don’t know how it’s scientifically possible, but my husband ordered a cocktail that had…clarified tom yum soup in it? His drink immediately transported us back to Thailand in the strangest way. He ordered another, and I had a half dozen of some of the best oysters around.

Central Provisions

Small plates are often a winner in my book, so you can have a bite of everything. I think this place was having an off night or just didn’t quite hit the mark. Bites were small and generously priced, leaving little to desire on either end. We waited long bouts of time in between dishes and drinks, so our appetite wasn’t ever satiated. The menu does rotate, however the tuna crostini and Barcelona fries were the best.

Taco Escobar

churros at taco escobar in portland maine

Since Central Provisions left us still feeling peckish, we were on the hunt for some nightcaps and grub toward the end of the evening. My brother-in-law Jake has lived in Portland for a while now and swore by the Mexican fare at Taco Escobar. No frills and fairly chill, we grabbed a few margaritas and some super tasty tacos to close out the evening.

Saturday: Along the water, bike and sample sweets

Eastern Promenade

eastern promenade portland maine

A simple two-mile stroll or smooth cycle along the water in Portland is the perfect way to spend a late morning. Filled with hipster couples and their rescue dogs, friends brunching and kids squealing, it’s such a cute and fun atmosphere to take in. The same people who designed this park also designed New York’s Central Park and Boston Commons. PS, the Canopy Hotel offers bike rentals, as does several local businesses.

Maine Maple Creemee Co

maple creemee soft serve cone in portland maine

If you catch the promenade at the right time, they often have food trucks along the walkway to indulge. This might be rarer in the winter, but we caught a few good ones in late fall. One of the highlights was the Maine Maple Creemee Co, featuring some incredible soft serve treats. Apparently, it’s a thing in Vermont that has its own little niche in Maine now. Fresh maple flavored ice cream with crumbled maple potato chips was unforgettable!

Portland Head Light on Cape Elizabeth

cape elizabeth lighthouse with bahn mi sandwich in maine

A quick drive out of the city brings you to some picturesque craggy coastline and plenty of classic lighthouses. The favorite was Cape Elizabeth, with its lighthouse dating back to the late 1800s. It’s a quick paved walk to the lookout points, which was nice and empty on a crisp early winter day.

Bánh Appétit

There are sometimes food trucks by the lighthouse, but we brought our own takeout to enjoy by the water. For a quick bite, Bánh Appétit offers delicious sandwiches and spring rolls that go down well with some Vietnamese coffee.


scales kitchen portland maine

After a luxurious, uninterrupted nap well-earned by two new parents, we got ready for a sophisticated dinner at Scales. I came to Portland for the seafood, and Scales did not disappoint. Menus are seasonal, but the grilled whole Branzino and mussels cooked in hard cider are two dishes to try. Have any f their steak and seafood paired with an array of fresh baked artisan breads too.

Sunday: Road trip back and pick-up some local goods

Oxbow Blending and Bottling

maine distilling craft cocktails portland

Our small crew are big beer buffs, so we had to peruse the plethora of breweries and distilleries in the city before heading back home. Oxbow is a solid choice for aged and mixed fermentation beers, alongside alternative boozy picks and some food onsite too if feeling hungry.

Allagash Brewing Company

allagash portland maine

Known across the county, Allagash is a tried-and-true brand of drinkable and delicious beer. It’s a bit outside downtown Portland, about a 15-minute drive, so we hit it up on the way back for some take home six-packs. When we visited the main retail space was closed though, so check ahead of time before going.

Maine Craft Distilling

maine distilling portland

I personally only have beer on occasion, so I was happy to find a spot that had some alternative options. Maine Craft Distilling has a verity of spirits to enjoy onsite or take home, but I especially loved their premixed cans. The Italiano Orange Spritz lookalike is getting me through this miserable winter by transporting me to sunnier Italian skies (or the ski slopes) with every sip.


meat dish at terulingua

One last hurrah in town brought us on an impromptu hunt for lunch that was one of the best meals we had all weekend. Part marketplace, part BBQ pit, part Mexican fare, Terlingua was ideal for some additional edible souvenirs and a nice meal out on the sprawling back patio. We had a shameful amount of tacos and some tres leche cake to take home, of course.

We plan to head back to Portland in 2022, this time maybe with the baby and our doggo, now that we found out the Canopy welcomes four-legged travelers too!

Have you been to Portland? What city do you love closest to your hometown?

More to read in and around Portland, Maine

Eileen Cotter Wright

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel journalist and owner of Pure Wander. She's our resident expat extraordinaire and falls down a lot in yoga class. Follow her on Instagram @Pure_Wander.

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