Did you know? Portland is the largest city in the State. But with less than 70,000 residents it dwarfs nearly cities like Boston. Despite its size, Portland has a ton to offer for any traveler.
Kickstart your day at Bayside American Cafe where the vibes are as cozy as their blueberry pancakes. It’s not just breakfast; it’s a tradition wrapped in a snug atmosphere. The menu is a blend of classic favorites and local flair, ensuring a delightful start to your Portland adventure.
Or indulge in breakfast at Holy Donut where every bite is a journey into unique, potato-based delights. Whether it’s the sweet maple bacon or the savory garlic parmesan, the atmosphere is quirky and charming, mirroring the spirit of Portland itself. My favs – Lemon Glaze or Dark Chocolate Sea Salt
Amato’s is a must-visit for The Maine Italian experience. Dive into tradition at their India Street spot – the birthplace of it all. Be sure to try it traditionally prepared using ham, American cheese, slices of tomato, onions, green pepper and sour pickle, Kalamata olives and salad oil. They also have pizza and pasta. Eat in or grab it to go.
Take a leisurely stroll down Congress Street, where art galleries like the SPACE Gallery and the Pearl Gallery await your exploration. Discover small businesses between High St and Monument Square, and make sure not to miss Reny’s – a family-owned legend with the mantra, “If they don’t have it, you don’t need it.” It’s a treasure trove of eclectic finds. Really, you can find almost anything in this store and snag some good deals from brands like Carhartt. The vibrant street art along Congress Street adds a unique touch to your Portland journey and Monument Square can’t be beat for people watching.
Catch enchanting views at Eastern Promenade, where food trucks spice up the day. If you spot The Totally Awesome Vegan Food Truck, give it a go – even non-vegans rave about it. Relax on the hill, soak in the harbor views, and let the day unfold. The panoramic scenery and the eclectic mix of food trucks contribute to the laid-back, authentic Portland vibe.
Exploring with your furry friend? Be sure to check out this doggie paradise tucked away in the heart of the city. Quarry Run Dog Park is a large off leash park where your dogs can really stretch their legs. There is a figure 8 shaped trail or if your dog is still perfecting their recall game, there is a fenced in area as well if you head to the left when you enter.
Immerse yourself in Old Port’s charm, where history whispers through cobblestone streets. Sturdy shoes are a must for the cobblestones, leading you to local shops and restaurants for daytime adventures. As the sun sets, the area transforms into a haven of local haunts, offering a glimpse into Portland’s nightlife while maintaining its historic allure. Be sure to check out Lincolns on Middle Street. They open at 5PM and if you can find it, you are in for a treat!
Located down on Commercial Street, Flatbread Co has some of the best flatbread pizzas I have ever tasted. Be sure to bring an appetite – the portions are huge! The ovens are in the dining room where you can watch them work their magic. I loved that all of the cooks seemed to love their job, dancing and bobbing their heads to the music while they were pulling pizzas out of the oven. Located right on the water, they offer outdoor seating in the warmer months so you can watch the working waterfront.
Save on transportation costs by utilizing the Greater Portland Metro Bus. Parking in the city can be pricey, but fear not – parking is only $5.50 per day at the Amtrak station, offering convenient bus access to almost anywhere in the city. They also have many connecting options at the station.
Greater Portland Landmarks has put together a bunch of free self guided tours that has something for everyone. Be sure to check out all the self guided adventures they have to offer.
Craving a more curated experience in Portland? Viator has you covered with an abundance of options, ranging from tantalizing foodie tours to captivating history expeditions, and serene harbor explorations. Whether you’re a culinary connoisseur, a history buff, or simply eager to soak in the coastal beauty, Viator offers a diverse selection of guided tours tailored to every traveler’s taste.
And that’s a wrap! These are my absolute favorites for your next adventure in Portland, Maine. Have you had the pleasure of exploring these gems? Drop a comment and spill the beans on your top spots – I’d love to hear about your go-to locations! Let’s swap stories and inspire each other’s next travel escapade.
Travel Turtles 