Portland Maine has earned a huge reputation for three major things, a foodie paradise, craft beer everywhere, and being exceptionally dog friendly. All of these are well deserved and make for a great trip.
What to do with Bowser
Casco Bay Mail Boat
The Casco Bay Mail boat is a great way to get out and see the water and islands in the bay and is very dog friendly. You need to buy a ticket for Fido and seating is a bit at a premium, so line up early. Hershey loved the wind in his ears and getting off at Long Island where the boat stopped for 15 minutes or so.
Baxter Woods is a unique “urban forest” park located in a residential section of the city. You can park along any of the streets and head in, and you’ll quickly forget you are in the middle of the city due to the dense foliage. The path is pretty short and you can get around the whole thing in less than 20 minutes, but the loop makes for a nice walk.
Portland itself may not have lighthouses, but within a 30 minute drive to the south are four including the Bug Light and Spring Point light in South Portland, Portland Head Light, probably the most picturesque, and the lights in Two Lights State Park. Bug Light is great for a picnic and has a nice field for dogs. Portland Head is a very picturesque lighthouse and has a nice walk along the cliff. Two Lights is less pretty, but has the fantastic and dog friendly Lobster Shack. No trip to Maine is complete without a moose sighting and several lighthouses.
East Prom Beach
East Prom Park itself is lovely and a great walk for a dog, but it really stands out for the beach at night. After 5:00 during the summer season, it opens for dogs and becomes a party. Strangely, dog owners in Portland are awesome and way less high strung than NYC. Dogs also seem to be in better control but this is no guarantee against incidents. Still, the beach is fenced in and pretty long, so it’s easy to make your own space. We couldn’t convince Hershey to go in further than he could stand, but he loved it so much he refused to leave.
Back Cove Park
Back Cove is the bay north of downtown Portland and makes for a nice morning walk. The path is a bit narrow in places, so if your dog is terrified of bikes like Hershey, it can be a bit hard to coax him around. However, the trail is very walkable at only about 3 miles. It’s not as scenic as East Prom, and a bit more industrial, but the north and east sections are nice.
Planet Dog Store
Planet Dog is a fairly regular pet store, but allows dogs and has a ton of awesome food, treats, and toys. The staff is awesome and loves well behaved pooches. Hershey picked out some duck treats here and even found some elk bones.
Antiquing at Portland Architectural Salvage and Flea for All
Portland has a ton of antique stores, but the two that stand out are luckily next door to each other and fairly dog friendly. At both, make sure to ask first if you can bring your dog in as we got a little scolded, but after meeting Hershey, he was allowed the run of each. Flea for all is a sprawling collection of every imaginable yard sale or flea market item from furniture to beer glasses. It covers three floors so make sure not to miss the small staircase. Architectural Salvage concentrates more on furniture and hardware and even has some interesting finds like a huge collection of door knobs.
Where to Eat
Eventide Oyster Company
Let me get this out of the way, Eventide was probably the best collection of seafood items I’ve ever had. Every dish was delicious including the raw items which I normally don’t go for. Best of all, the outdoor seating area in front is dog friendly. Get your name in here very early or you’ll be stuck waiting with the crowds until midnight.
Oyster shooter with jalapeno infused vodka
Octopus salad. Great collection of summer flavors including corn, queso fresco, and of course my favorite mollusk. I could have used a bit more octopus, but that may be the Croatian octopus salads speaking.
I love tentacles.
Lobster chowder or chowdah. If you like Thai coconut soup or lobster, or want to enjoy life, this is the dish for you. Huge chunks of lobster are swimming in a delightful curry soup. More please!
Lobster roll. Unlike either the cold Maine lobster rolls or the warm Connecticut style, this is more like a pork bun with lobster. It’s as good as it sounds.
BBQ Broiled Oysters. At the oyster house, you have to get oysters. Even if you aren’t a fan or raw oysters, you have to get this. We liked it so much we ordered a second round. The huge oysters are delicious and swimming in a tangy bbq broth. The cabbage and potato crisps added a nice texture.
Crab Roll. It may look bland, but the crab meat is packed with flavor and soft and delicious.
Ice Cream Sandwich Cookie. Just do it!
In a city of seafood, Duckfat is a bit of an oddity with it’s high end sandwiches. Styled as a Belgian frite joint, the frites are definitely awesome as they are fried in duck fat, hence the name. The tables outside are dog friendly, but the wait can be extraordinary. Instead, get an order to go and either enjoy it on the green lawn in front, or take it on the Casco Bay Mail Boat for a delicious snack. Pro tip: Pick up some beer from the dog friendly Craft Beer Co and bring it on the boat as well.
Portland Lobster Co
There is nothing better than enjoying fresh seafood under the stars right on the water. Therefore the lobster company is a pretty good way to spend a night. The huge deck is dog friendly and often has live music. The lobster is outstanding here whether it is a roll, a whole lobster, or this tasty mac and cheese with chunks of lobster in it. They even have a pretty good craft beer selection with local brews.
The Lobster Shack
Lobster rolls by the sea. It doesn’t get much more Maine than this. I don’t like the Maine style roll which is cold meat with mayo as much as the warm butter Connecticut style, but this one was pretty great. Despite the location away from the city, be prepared for long lines. The outdoor picnic space is huge and super dog friendly.
The Front Room
The Front Room should be your go to brunch spot in Portland. It is located in the “Brooklyn of Portland”, Marjan Hill, and has some great brunch items. The outside seating is dog friendly as is the staff. Go for anything with egg.
Despite a visit from Anthony Bourdain, J’s was a bit of a disappointment. It’s definitely a local place and pretty authentic for Maine, but the seafood and service were lackluster. The seating out on the water was nice, but kind of felt like you were in a parking lot. The steamers are famous for good reason and while a bit of a pain to eat, very tasty. The clam chowder was not great as it took forever to come out and was served fairly cold.
Portland probably isn’t known for ice cream, but the gelato here is excellent. The inside is not dog friendly, but Hershey loved a lick of the melty cream.
The Holy Donut
For breakfast, you owe it to yourself to get one of the decadent donuts from The Holy Donut. The downtown one does not have seating, but the one further out has several outdoor tables where good dogs are allowed. Hershey enjoyed the maple bacon but would have liked some peanut butter.
Where to Drink
Sebago Brewing Company
Not a ton of ambiance at Sebago, as it is basically in a hotel, but the beer is great and they allow dogs outside. The seasonals are also great.
Thirsty Pig is a silly name but there is nothing silly about the great beer selection here. Dogs are allowed on the lower patio which has a few picnic tables and some benches. The bartenders are a little surly, but the great local craft beer on tap here is very welcoming.
Gritty’s is definitely not a high fallutin’ kind of place, but the beer here is top notch and the food isn’t bad either. There are three or so tables outside in the alley which has surprisingly good people watching. The Halloween ale was delightful.
BBQ Pork and cheese sweet potato fries. I think the picture speaks for itself.
Rising Tide was probably the best atmosphere of any brewery we visited. The outdoor tables are great and hey had live music. The beer here was pretty good too though too many IPAs in my opinion.
The best coffee in Portland period. The space is nice and light and seems like a great place for working with your brew. Go for the Nitro Cold Brew because just like beer, nitro is always better. Not dog friendly inside but they do have two tables outside or you can take your coffee down to the water.
Good coffee but very pretentious staff in my experience. The inside is tiny and not dog friendly so take it to go. They do make fruity pebbles milk here which can be added to any coffee and is as good as it sounds.
No longer dog friendly inside or at the back garden, but the tables in front are. They have the town’s best vietnamese lattes here.
Where to Stay
The Inn at St. John
The Inn is a great place to stay with a dog. The breakfast is included and fairly basic, but good enough to get you to your next lobster roll. Super dog friendly and best of all, they have bottles of water in the lobby which are great for exploring the town. It’s a little of a walk to downtown, but pleasant enough.