All About Portland

About Portland

Portland is a small, hip and happening city well known for its killer dining and craft beer scene. There’s so much to eat and drink in this awesome little city!

PORTLAND NEIGHBORHOODS IN SHORT

At about 21 square miles, Portland has more neighborhoods than the three mentioned below. But these neighborhoods are the city’s most popular, visited destinations and they’re all quite walkable from one another - especially if you’re used to walking in bigger cities.

The Old Port

Centrally located and incredibly charming with its cobblestone streets, The Old Port and in particular, Exchange Street, is the heart and soul of Portland. There are tons of shops, restaurants, bars and hotels here. And while it’s most certainly the most touristed area of the city, there is still a lot of great stuff to indulge in here. On summer weekends especially, the Old Port gets very noisy and lively, which can be awesome or awful depending on your personality.

West End

A more residential and upscale part of Portland, the West End has some absolutely lovely restaurants and beautiful tree lined streets and Victorian architecture to swoon at. Things are more quiet over here but the Old Port is just a brisk walk away.

East Bayside

Missed by many tourists, East Bayside is one of Portland’s most quirky, progressive, hip neighborhoods that is chock full with killer eats, breweries and shops. With less tourists over here, East Bayside feels more authentically urban. I absolutely love it.

Where to Stay

In the past we have enjoyed stays at the Portland Harbor Hotel, which has a wonderful location smack dab within the action of the Old Port, and the Press Hotel, which is equally nice with really great service and staff. It’s also in the Old Port. You can’t go wrong with either place. They’re both nice, clean, well situated city hotels that you’re mostly using to crash at night. In Summer 2022 we tried the Francis, a historic property turned boutique hotel in the Parkside neighborhood directly across the street from Tandem (see below!). It’s a really hip, boutique hotel in the West End, but not as centrally located as the other two hotels mentioned.

What to Do

The best thing to do in Portland is to soak up every ounce of its glorious food and drink scene. Relax over natural wine and oysters or meet up with friends at a craft brewery. There’s so much good, mom and pop shopping in Portland. And like any city, the people watching is fun here. Read on for some kid-centric ideas in Portland.

In between bites and sips, take your kids to one of the several playgrounds around the city. Past summers we have spent a lot of time with them at the splash pad at Deering Oaks Park.

In Summer 2022, we visited the reimagined and relocated Children’s Museum of Maine in Thompson’s Point. Even as one of the older kids there, our younger one had an absolute blast, particularly in the museum’s imaginative play area.

The Old Port area of Portland is filled with cute shops set along cobblestone streets. There’s something for everyone there, but your kids will especially love Treehouse Toys and Old Port Candy Co.

What to Eat

There’s so much to eat! Portland has world class fine dining and killer lowbrow sandwiches and snacks. For a smaller sized city, Portland has an outsized dining scene and it’s constantly evolving and growing. I’ve set out all our favorites below that we’ve made it to so far (still more to do!) and noted where a car would be needed, assuming you’re staying in one of the touristed neighborhoods above.

Breakfast (Coffee/Pastry)

Tandem Coffee + Bakery - a Portland Maine-STAY (hehe). Tandem is must do. Their larger location in Parkside across from the Francis is always packed. In Summer 2023 we were a few minutes from their smaller East Bayside location. I LOVED how this location was far less touristy and more relaxed. Tandem is all around incredible - consider ordering their loaded biscuit (with butter and strawberry jam!), chocolate chip cookie, spiced molasses and ginger cookie and/or cheddar jalapeño scone.

Zu Bakery- a bread bakery found a permanent West End home in late 2022 and Portland is better for it. Breads are all naturally leavened and wood fired at this artisan shop. Only a few products come out at a time as they’re ready. Zu’s croissants are perfectly flakey.

Night Moves (Car Needed) - it’s worth driving to South Portland for what may have been my favorite baked goods of Summer 2023. Previously in Biddeford, Maine, Night Moves reopened just as we arrived in Portland. It’s a beautiful setting along the water and our baked goods (hello cornbread!) were incredible. Like Zu, Night Moves also has a very strong bread program.

Rose Foods (Car Needed) - a counter service Jewish deli by the same people who own and operate the incredible Palace Diner in Biddeford, Maine. On my visits, I’ve gotten the Classic Nova - cream cheese, nova, cucumbers, onion, capers, dill - on an everything bagel, and it was a perfect blend of salty herbaceous goodness. My husband concocted his own order with whitefish salad on an everything bagel.

Breakfast (Sit Down)

Bread and Friends - a daytime restaurant and bakery that just opened in Spring 2023, Bread and Friends is already super popular in Portland. The bread products and baked goods are excellent, as their name implies, but so are the composed dishes. A wonderful way to experience the community feeling of Portland.

The Ugly Duckling - another new for 2023 spot, this time in the West End, the Ugly Duckling is the luncheonette of your dreams. On our breakfast visit, a few pastries were offered but the star of the show is the restaurant’s house made buttermilk English muffin and the various sandwiches that showcase them. The horseshoe bar at the Ugly Duckling is such a vibe, you’ll want to order a cocktail and stay through lunch.

Lunch

At lunchtime, you probably want to find yourself at one of Portland’s many craft breweries or wine bars. Lucky for you, some great lunch options can pair well with that plan. I’ve also listed below a few “grab and go” lunch options.

Bissell Brothers (Car Needed)- probably the most well regarded of the Portland breweries operating today (known especially for IPAs), Bissel Brothers is conveniently located mere steps from the Children’s Museum of Maine and offers a full food menu. During weekend day time hours, it is packed with families.

Oxbow Blending and Bottling - if you want to wet your whistle with a crisp farmhouse ale, you really can’t do any better than Oxbow’s East Bayside location. Oxbow has a large indoor tasting room and an equally large outdoor patio plus Duckfat Friteshack is on property. Do NOT skip an order of Belgian frites with one or more of their homemade dipping sauces (I personally love the truffle ketchup and garlic mayo). It goes so perfectly with beer. I think this place is my version of heaven.

The Shop - just a few steps away from Oxbow (I LOVE East Bayside), the Shop is an ultra hip oyster bar and tinned fish spot, that’s perfect for day time snacking and drinking.

Mr. Tuna - a Portland icon specializing in hand rolls. In 2024 Mr. Tuna finally opened a true brick and mortar location in the Old Port, but on a beautiful day, I recommend hitting its mobile sushi truck parked at the stunning Eastern Promenade.

SoPo Seafood (Car Needed) - a market and raw bar, SoPo Seafood is offering seafood that is both as fresh as can be and very reasonably priced. Does lunch get any better than some raw bar, a fish sandwich and a glass of wine? SoPo also offers some raw items “by the spoon,” allowing guests a well priced taste of something from the fish counter. A REALLY great spot now part of our regular rotation.

Ramona’s - the same crew that does Rose Foods also has a hoagie spot Ramona’s in East Bayside.

Dinner

Dinner time in Portland is where things get tough. You’d need months in Portland to get through all of its offerings. We’ve knocked a few great spots off our list and I’m sure by next summer there will be 10 new spots to try.

Crispy Gai - this Thai influenced stunner in the Old Port is probably our favorite restaurant in Portland. Everything about it just works and all of our visits have been outstanding. Crispy Gai specializes in crispy, juicy fried chicken and incredible house made sauces to pair with it. But don’t sleep on their wok made rice dishes and certainly DO NOT miss the drink program here. Every mocktail and cocktail we’ve had here was outstanding - perfectly balanced, unique and delicious tropical cocktails with Thai influences.

Cong Tu Bot - an effortlessly casual but hip Vietnamese restaurant in East Bayside, Cong Tu Bot, is another Portland “must do.” The menu is full of bright and delicious Vietnamese dishes. They also have great natural wine.

Wayside Tavern - located inside the Francis Hotel (see above) in the Parkside neighborhood, this is a really special spot for some excellent dining and drinks. Do NOT skip the opportunity to order incredible broiled oysters and scallops by the piece.

Fore Street - the “Grand Dame” of Portland, Fore Street opened in the Old Port back in 1996 and is still drawing crowds today for its rustic, wood-fired dishes and farm to table ingredients. This is the perfect spot if dining with folks who love less adventurous but still delicious food.

Central Provisions - another Portland icon, Central Provisions, is an internationally influenced small plate restaurant in the Old Port that has been popular since its open in 2014. A great date night spot, Central Provisions has a dark, intimate atmosphere and offers mostly bar seating that surrounds the chefs as they cook.

Regards - this restaurant in the Arts District feels more LA, CDMX and NYC than Portland. Regards was the only Maine restaurant to make Bon Appetit Magazine’s 2022 Best New Restaurants list. We enjoyed our meal and the ambiance here a lot. Service was friendly but very slow and disjointed.

Leeward - an Italian restaurant also in the Arts District that opened just a few days before the entire country shut down for COVID. Think house made pastas and focaccia and delicate starters like burrata and a lightly fried vegetable fritto misto. Delicious.

Bar Futo - a Japanese Binchotan grill (charcoal) restaurant in the Old Port by Jordan Rubin of Mr. Tuna, Bar Futo is lots of fun. You must get a bunch of skewers (the Big Mac is UNREAL), but don’t skip the diverse non-grilled small plates. We loved the Crispy Eggplant in Spicy Garlic Miso.

Terilingua - Texas BBQ with South of the Border influences at this East Bayside market and restaurant.

Eventide Oyster Co. - a seafood small plates restaurant that’s long been getting heavy praise in Portland and is always packed (now with a second location in Boston, MA!) We enjoyed years ago, but probably will never go back since there are so many newer spots to try.

Chaval - a Spanish/Mediterranean spot in the West End. Everything was perfect on our visit; I had Maine blue fin tuna and my husband raved about his steak. Don’t skip their patatas bravas or desserts.

Mami - we had a great lunch at former food truck turned brick and mortar Japanese izakaya in the Old Port. Everything we had there was yummy, but the fried hake sandwich was something I will think about for awhile.

Highroller Lobster - I resisted coming here for so long with only a night or two in Portland to spare. But on my much longer visit in Summer 2023, I had to have a lobster roll for lunch one day and Highroller hit the spot! Had a great Bissel Brothers IPA while here too. This restaurant is very popular and family friendly.

Bars

Almost every restaurant in Portland leans heavily into the local craft beer scene and also offers a rather strong craft cocktail menu. I was also so happy to see natural wine on so many restaurant menus. Beyond the restaurants and breweries, there are FOUR bars in Portland that I strongly recommend.

Novare Res Bier Café - this is an elite beer bar that pulls from the owners’ travels around the world. You’ll find local favorites on the menu but also so much more. There are good beers from all over the globe. And the atmosphere of this bar, tucked into an alley in the Old Port, is so damn cool. I could stay all day. PRO TIP: Their house made French Onion dip is the perfect companion to a refreshing beer.

Room For Improvement - this bar in the Old Port needs absolutely no improving. It’s a cocktail bar without pretense and a casual dive with an elevated bar program. The vibes and drinks are so immaculate, I will visit every chance I get.

MAPS - in researching for this most recent trip to Portland, MAPS came up frequently as a recommended bar in the Old Port. Reviews (and my Uber driver) noted it can get loud in here, but when I came by for a pre-dinner drink, both the relaxed but lively atmosphere and my cocktail were perfect. Will definitely add a visit to all future Portland visits.

Portland Beer Hub - Portland’s only craft beer shop, Portland Beer Hub is a great alternative to visiting every Maine brewery separately. This adorable shop and bar carries almost exclusively Maine beer and it’s located right in the center of the Old Port. Visit for a pint or take single cans home to go.

Portland’s dining and drinks scene is SO strong!