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Portland, Maine Travel Guide

Portland, Maine Travel Guide
By Emma Gresh Special to Bearfoot Realty

If there’s one thing lifelong Maine residents and leaf peepers alike can agree on, it might just be that Portland is a city worth the visit. This sweet seaside town, set alongside the scenic coast and teeming with tasty restaurants and brimming with breweries, is beloved by all who spend time there – and for good reason. It’s quaint, it’s filled with activities for year-round fun, and it’s easily enjoyed as a day trip or a daily destination. So whether you’re contemplating a move up the coast or looking for the best ways to explore your home state, we’re here to help you enjoy the quintessential Maine experience by taking advantage of all that Portland has to offer.

For Early Risers

Your scenic tour of Portland can start as early as you’d like, with a plethora of coffee shops to kickstart your day. Bard Coffee and Forage Market are certified Bearfoot favorites, with the latter guaranteed to serve up not only an amazing latte, but also the best homemade bagel breakfast you’ve ever had. 


You could spend a day in Portland simply wandering the city streets, but there’s a few must-see spots to make sure are on your list to truly round out the experience. 

Start the day shopping downtown along Exchange and Commercial Street. There are enough local shops to pop into here to keep you occupied for hours, from hand-crafted clothing to freshly-painted pottery. Once you’ve shopped to your hearts’ delight, you won’t want to miss wandering through the streets of the West End. The Victorian homes scattered along the water will transport you right into a fairytale. Then, to enjoy sweeping views of the coast, take a stroll along the Eastern Prom, and don’t be afraid to pay the food trucks along the hill a visit.

To take the views up a notch, we recommend heading a little outside the city. Both Fort Williams and Two Lights State Park offer the perfect setting for a scenic stroll with lighthouse views. Or, if you’re looking for a bigger adventure, take a day trip to Peak’s Island – the ferry only takes fifteen minutes, and you can rent bikes to tour the whole island!

In the warmer monthsarguably one of the best parts of Portland is the proximity to some of Maine’s best beaches. Higgins Beach, Pine Point, Crescent Beach, and Willard Beach are just a few Bearfoot favorites in the area, but you really can’t go wrong with any spot to soak up the sun! And if you time your visit right, you can end your beach day with a concert at Thompson’s Point. This is one of the best summer activities in town, with great talent in an intimate, oceanside venue.

Speaking of the sun, there’s no better spot to watch the sunset than Bug Light Park in South Portland – best enjoyed with a personal picnic. But don’t worry, the fun doesn’t end once the sun goes down!

For the Foodies

All this exploring will likely have you working up an appetite in no time. It’s no secret that Portland is a foodie city, and it may feel overwhelming to sift through the many delectable options on the menu. So we’ve tried the must-do’s and the secret spots, and consolidated all of the Bearfoot favorites just for you!

For breakfast, we’ve already mentioned Forage, but we’d be remiss not to direct you to The Holy Donut, home to the best donuts you didn’t know you were missing out on. They’re huge, they’re hand-made from potatoes, they’re offered in an assortment of one-of-a kind flavors, and they’re amazing. Enough said.

For lunch, Sisters Gourmet Deli is cute, it’s funky, and it is confirmed to be gourmet indeed. This delicious sandwich shop right in the heart of the Old Port is known for its homemade bread and the menu leaves nothing to be desired. Additionally, The Lobster Shack has one of the best lobster rolls in the state, in our humble opinion. A trip to Portland wouldn’t be complete without one, and why not enjoy one complete with a lighthouse view – it doesn’t get better than that! Or, if you’d rather stay right downtown, Eventide is a small seafood spot that is always bustling, and for good reason. Their brown butter lobster rolls are a unique take on a classic Maine staple, and well worth the wait. Duckfat is another popular destination that locals and tourists alike quite literally line up for, and with some of the best french fries you’ll ever taste, we can’t help but recommend that you line up for a meal, too.

For dinner, we’ll start casual. Otto is a unique pizza joint, best enjoyed on the go. If you’re feeling a little adventurous, there’s no better place to go for anything from a butternut squash and cranberry to a three-cheese tortellini slice. For a sit-down wood-fired pizza experience, Flatbread consists of an open airy atmosphere, a bar stocked with loads of local beer, the cozy warmth of brick-oven pizza ovens, and an outdoor deck on the water – you can’t go wrong. If you’re looking to take things up a notch, The Rooms provide three top-notch meal options in an array of cuisines. A cozy Italian dinner can be found at The Corner RoomThe Front Room offers elevated American fare, and if a steakhouse is calling your name, The Grill Room will not disappoint. For upscale dinners, Street and Co. is the perfect establishment for a nice night out, with a menu filled with amazing Mediterranean seafood dishes. Evo offers an incredible array of Mediterranean small plates with a unique twist, and Via Vecchia is a small-plate Italian spot filled with amazing flavors and an even better atmosphere. Lastly, Scales is newer to the neighborhood and boasts some of the best Maine seafood around. Make sure to grab a reservation early, and don’t miss out on the brown bread to start! 


If you’re feeling parched after all these activities, no problem. There’s a drink for that.

During the day, you can stop at Novel to enjoy a drink in a cozy cafe setting. And of course, it wouldn’t be a trip to Portland without a stop (or two, or three) at some of the local breweries. There’s a ton to choose from, but Rising Tide and Après are Bearfoot favorites for their cozy atmospheres and assortment of beverages. 

Later on, you can visit Bayside Bowl for bowling AND a rooftop bar for happy hour, or enjoy live music at The Porthole outside during the summer. And for pre-dinner drinks, there’s no better spot for a craft cocktail than Blyth and Burrows.

After dinner, head to Lincolns for five dollar post-dinner drinks – if you can find it – or even better, top off your night with a drink from The Bar of Chocolate. Their Salted Caramel Chocolate martini is even better than it sounds!

That’s a wrap on our Bearfoot-approved Portland travel guide. While this by no means captures all there is to do in our great city, it’s a collection of spots guaranteed to spark an appreciation for the state we call home. Enjoy – it’s called Vacationland for a reason.

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