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  • Writer's pictureKatie Wright

How to Spend a Weekend in Portland, Maine

Wondering what to do in Portland, Maine? I am so excited to share our guide to a perfect weekend in Portland Maine sampling all of the best restaurants, breweries and things to do in the area. Portland, Maine is set on a peninsula extending into Casco Bay. We stayed in the Old Port waterfront district which features working fishing wharves and converted warehouses with restaurants and shops. It's a small city but absolutely packed with adorable boutiques, fantastic breweries and diverse (and delicious!) dining.

Lewis and I recently celebrated his 30th birthday in Portland, Maine and it was a perfect weekend trip from our hometown of Boston.

Our main (Maine, haha get it...) goal for the weekend was to visit as many breweries as we could and eat delicious food along the way--and I would say we did a very good job of accomplishing that goal!

We drove up to Portland on Friday morning to check into our hotel, the Hyatt Old Port. The Hyatt Old Port was in a perfect location right in the center of Old Port and was walkable to many of the restaurants, shops and breweries that we wanted to visit.

After checking in we visited our first brewery of the trip: Liquid Riot. Liquid Riot was right in the center of Old Port and had a great waterfront porch.

From Liquid Riot we made our way to Shipyard Brewery which is one of the bigger ones in the area. Shipyard probably had our least favorite drinks of the weekend but it did have a Friday happy hour with a self-serve raw bar which I definitely took advantage of!

When planning the trip to Portland I was overwhelmed with the many, many amazing restaurant options to choose from for a special birthday dinner for Lewis. We settled on Fore Street and I was lucky enough to snag a reservation exactly 60 days in advance (they book out quickly!). Fore Street was featured on one of my favorite foodie shows, The Zimmern List, so I knew it would be worthwhile. It didn't disappoint!

Fore Street is part of a family of restaurants and bakeries that include Street & Company, Scales Restaurant and Standard Baking Company (also a must-visit!). All are located in Portland. Fore Street's interior was warm and cozy due to an open kitchen centered around a wood-burning oven, grill, and turnspit, visible from most tables. The service, food, wine and atmosphere all earned the meal an easy 10/10 from us. Highly recommend!

Other restaurants that looked amazing:

  • Honeypaw - Asian fusion. Reservations recommended.

  • Central Provisions - Tapas/small plates, reservations recommended.

  • DUCKFAT - Pro Tip: If you want the full experience go to the restaurant BUT the locals trick is going to Oxbow Beer Garden for drinks and they have a Duck Friteshack where you can get the famous poutine and fries! (This is what we did!)

  • Street and Co - Looks so good! Mostly just seafood on the menu, reservations recommended.

  • Scales - Seafood with some land options, reservations recommended.

  • Eventide Oyster Co - Seafood, reservations recommended.

  • Highroller Lobster Co - Looks a little more casual but so cute. I've heard it's the best lobster roll in town.

  • Luke’s Lobster - Great pier outdoor location with views.

The next day, Saturday was when our self-guided brewery tour began. But before we could start drinking we grabbed some breakfast at Becky's Diner. Highly recommend the Maine blueberry pancakes! From the diner we wandered into a few of the boutiques around town. My favorites for home decor and accessories were:

But there are so many to choose from. Portland also has a great thrift and vintage shopping scene which we have really enjoyed in previous trips!

But now, on to the breweries....

Our first stop was our favorite brewery from our last visit to Portland: Bissell Brothers. We took an Uber from Old Port to Bissell Brothers around noon and snagged a booth inside. In addition to great beer we love the food at Bissell. Chef Benjamin Martinkovic makes use of as much local produce, meat, and seafood as possible with a menu featuring plates big and small. Offerings include sandwiches, tacos, salads, and charcuterie with options for those who eat vegan and gluten-free. We ordered the short rib tacos and they were fantastic.

From Bissell Brothers we Uber'd to Anderson Street which had probably about 15 breweries all in a row! We visited Goodfire and Lone Pine which were pretty good but not our favorites.

Then we walked over to Aprés which was an unexpected treat. Aprés didn't actually serve beer, instead they had a variety of unique hard seltzer and hard cider options which were super refreshing. Aprés also just had an awesome ambiance that made us want to sit and hang out in there all day. Aprés wasn't even on our radar of places to visit but absolutely turned into one of our favorite spots of the weekend. Definitely recommend!

From Aprés we walked on to Austin Street Brewing where I needed more food to get me through this marathon. Luckily they had a sushi truck at Austin Street and I ordered some spicy tuna rolls. From Austin Street we Uber'd again to our final destination: Oxbow. Oxbow was probably my third favorite of the day after Bissell Bros and Aprés. The fact that there was a really cute golden retriever puppy there might have helped. We also loved the Duckfat Friteshack set up at Oxbow so we could have some delicious fries with our beer.

Finally, we made our way back to Old Port where we had our last drink of the day (and dinner) at our favorite dive-y bar: Mash Tun. Burgers are only $6!

If you think our day of eating ended there though, you're wrong! We also had to stop at Mount Desert Island Ice Cream for some unique locally flavored homemade ice cream. I had the Fresh Basil and the Maine Sea Salt Caramel (INCREDIBLE).

There were a ton of cool after-hours bars that were recommended from friends but at that point of the day were were so stuffed we couldn't even think about going to one more place. But if you're interested Blyth & Burrows and Portland Hunt and Alpine Club both came highly recommended for cocktails.

Sunday morning, we somehow managed to make room for Portland's famous Holy Donuts which are handcrafted potato donuts. We also couldn't leave without a bread haul from Standard Baking Co.

And that was our weekend! I am simultaneously hungry and full just thinking about all the amazing things we ate and drank in the space of 72 hours in Portland, Maine! It's such an awesome destination all year long but I think it really shines in the Spring and Summer when you can take advantage of all the outdoor and waterfront spaces. We are already planning our next trip because there is still so much to see (and eat!).

What are your favorite things to do and see in Portland, Maine? Did we miss anything? Drop us a comment and let me know what you loved and what we need to do next :)


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