Ah, Portland. The sweetest seaside town teeming with tasty restaurants, brimming with breweries, and filled with some of my favorite memories. Earlier this month, I took a quick trip back to the homeland with my boyfriend for a wonderful weekend filled with great food, fun, and some of my favorite people, and it got me thinking that I have never documented all my favorite spots in this cute little city! It’s quaint, it’s walkable, it’s coastal, and it’s all able to be enjoyed within 1.5 hours of Boston. So without further ado, allow me to share some of the many options to choose from in order to have the perfect short but sweet weekend getaway!
Activities in Portland, Maine
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.
Shop Local
Begin your day downtown on Exchange and Commercial Streets, where you’ll find a mix of locally owned shops offering everything from handmade pottery to curated fashion. There’s local Maine charm to be found around every corner.
Walk the Eastern Promenade
For panoramic views of Casco Bay, head to the Eastern Prom – and don’t be afraid to pay the food trucks along the hill a visit. It’s the perfect spot for a scenic stroll or an afternoon picnic.
Visit the West End
The Victorian homes scattered along the water in the West End will transport you right into a fairytale – and offer a peek into what Portland Maine real estate has to offer.
Explore the Area
To take the views up a notch, I 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!
Hit the Beach
In the warmer months, arguably 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 a few personal favorites in the area, but you really can’t go wrong with any spot to soak up the sun!
Sunset at Bug Light Park
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!
Catch a Show
If you’re visiting in summer, end your day with a live concert at Thompson’s Point, one of Maine’s best outdoor venues complete with ocean views.
The Best Restaurants in Portland, Maine
Breakfast Musts
Your tour of Portland can start as early as you’d like, with a plethora of coffee shops and breakfast joints to kickstart your day.
Bard Coffee is a local go-to for the perfect cup of joe or specialty concoction.
Forage Market is guaranteed to serve up not only an amazing iced latte but also the best homemade bagel breakfast you’ve ever had.
And of course, The Holy Donut deserves a top spot on your morning hit list. Made with real Maine potatoes and offered in flavors like maple bacon and sweet potato ginger, these donuts are a local legend for a reason.
Lunch Favorites
Whether you’re feeling a light bite, a lobster roll, or something with a little extra flair, we’ve got you covered.
Sisters Gourmet Deli is cute, it’s funky, and it is indeed gourmet. 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.
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, complete with a lighthouse view.
Eventide is a small seafood spot right downtown 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, I can’t help but recommend that you line up for a meal, too.
Dinner Destinations
It’s no secret that Portland is a foodie destination, and dinner is really where this city shines. I’ve included a few favorites below, but trust me when I say that you really can’t go wrong with most places around.
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 offers an open and 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 Room, The Front Room offers elevated American fare, and if a steakhouse is calling your name, The Grill Room will not disappoint.
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.
Via Vecchia is a small-plate Italian spot filled with amazing flavors and an even better atmosphere – especially if you dine on the patio outside their stately ivy building.
Scales is newer to the neighborhood and boasts some of the best Maine seafood around. I saved the best for last here – make sure to grab a reservation early, and don’t miss out on the brown bread to start!
The Best Drink Spots in Portland
If you’re feeling parched from all of these activities, no problem. There’s a drink for that.
During the day, you can stop at Novel to cozy up in the stacks with a daytime coffee or cocktail nestled inside a bookstore.
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 my personal favorites for their laid-back vibes and wide variety of beers and beyond.
Enjoy live music and ice-cold drinks outside at The Porthole during the summer.
Blyth and Burrows is a stylish spot for a craft cocktail, perfect for date night or a pre-dinner drink.
Head to Lincolns for five dollar drinks in a hidden speakeasy setting – if you can find it.
Top off your night with a drink from The Bar of Chocolate. As you might expect, their menu offers all sorts of dessert cocktails, and their Salted Caramel Chocolate martini is even better than it sounds.
Come back soon!
It’s such a treat returning to my home state now that I can truly appreciate all that it has to offer, and I hope this guide helps you experience some of that Maine magic. Until next time! ☼
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