Portland, Maine Travel Guide
While Portland is a great destination regardless of where you live, I especially love that it’s such a short trip from Boston. A city that’s so close (an hour and a half or so by car) and can actually feel like you’re a flight away is the most ideal feeling for a weekend getaway. I can’t help but think of Portland as Maine’s version of Newport: there’s a lot of history and charm, with enough small shops and award-winning restaurants to keep you here for weeks—all located directly on the water. My favorite parts? The abundance of fresh oysters and lobster and the encouraged happy hours!
For more New England travel recommendations see 5 Scenic Road Trip Destinations in New England and 20 Things To Do in New England.
What are your favorite restaurants, activities, and stays in the city of Portland? Let us know in the comments below!
Portland, Maine Travel Guide
Where To Eat Portland Maine
Fore Street
Fore Street is a must! Reservations book up very far in advance but I think this is the best pick for quintessential Portland — farm to table ingredients, rotational offerings and a cozy, upscale vibe.
Eventide
Eventide is worth the wait for this lobster roll alone! Trust me — the constant crowds of people don’t lie.
Duckfat
Although deemed a tourist hotspot, the poutine at this quaint, yet well-known spot is really (really) great. Don’t miss Duckfat!
Blythe and Burrows
Blythe and Burrows is one of the best craft cocktail bars I have ever been. You know those places where the bartenders are like artists? Like that, in a super cool speakeasy atmosphere.
The Shop
Head to The Shop for the best oysters from the well-known Island Creek Oysters. Sit out on their open patio, located just a few blocks from the bustle of downtown.
Scales
Scales has a great location, views, and a fantastic menu.
The Holy Donut
The Holy Donut is another Portland must! The Maine Blueberry is my favorite.
Sur Lie
Sur Lie is great for happy hour and tapas.
Best Places To Stay Portland Maine
There are so many great stays to enjoy in Portland. From great downtown locations to roomy Airbnbs, take your pick from some of our favorites.
Press Hotel
The Press Hotel is located in the Old Port district and has an old newspaper theme within walking distance from some great restaurants and shops.
Portland Harbor Hotel
You can expect a convenient location, clean rooms, friendly staff, and Starbucks coffee at the Portland Harbor Hotel.
Airbnbs in Portland Maine
Are you looking for something a little more spacious and private? Portland also has a lot of great Airbnb options. I suggest staying within walking distance of the Old Port.
Things To Do in Portland Maine
Wine Tasting
Portland may be known for its craft beer, but at the city’s newest wine bar, Grippy Tannins, you can enjoy a number of wines in an ultra chic and comfy setting.
Portland Museum of Art
Portland Museum of Art is the largest and oldest public art institution in Maine, located in the Arts District.
The Portland Observatory
The Portland Observatory is a historic maritime signal tower and is the only of its type in the U.S. Don’t miss this important part of America’s history!
Boat Rides and Whale Watches
While there are too many to list here, Portland offers many boat cruises and whale watches, if you’re interested in soaking up as much ocean-time as possible.
Live Music
Portland has great options for live music. My favorites were the Thirsty Pig and Portland Lobster Co.
Perkins Cove
A short drive out of the city will bring you to Ogunquit, Maine, home of Perkins Cove. Go here for a stroll along the cliff walk (also very Newport-esque), cute shops, and multiple restaurants to indulge in casual summer food from whole lobsters to burgers.
Acadia National Park
If you are looking to explore and enjoy the beauty of Maine’s coast and forest you can drive 3 hours up the coast to Acadia National Park on Mount Desert Island. Explore the town of Bar Harbor for great restaurants, hotels, and shopping, and head to the park for hiking, biking, and boating adventures.
South Portland
Home to historic lighthouses, Willard Beach and the Greenbelt Walkway Trail— South Portland is a beautiful part of Portland to explore!
Columbia River Gorge
30 miles east of Portland is the Columbia River Gorge— the perfect place to hike, swim and explore!
Explore Small Town Maine
There are so many quaint and idyllic New England small towns to explore outside of Portland. Head to Cape Elizabeth, Freeport, Camden or Kennebunkport for a fun adventure.
Where to Shop In Portland Maine
Flea For All
Flea-For-All is a large vintage market, fun to treasure hunt through.
Exchange Street
Exchange Street is the perfect place to venture for everything from clothing to souvenirs, ceramics and stationary, this busy little street has something for everyone. And when shopping gets exhausting, head into the Thirsty Pig or Blythe and Burrows for a craft beer or cocktail.
Pinecone and Chickadee
Pinecone and Chickadee is a fun-to-explore shop that offers a variety of items, including VHS and Polaroid cameras!
Strata
Walk up a few blocks from the bustle of Old Port to the ‘Black Boxes’, and you’ll find Strata, a dream come true for the home chef in your life. The craftsmanship of this culinary knife shop and whetstone sharpening service is pretty impressive, even if you aren’t going home with a hefty Japanese knife.
Mulxiply x Campfire Studios
Located in the micro space next door to Strata, this space offering jewelry and leather goods from Mulxiply and ceramics from local brand Campfire Studios is bound to be the perfect spot to pick up something for a loved one, or yourself, on your trip.
Portland is the perfect place to venture for deliciously fresh seafood, great shopping and entertainment, and elegant stays. Enjoy a getaway in one of our favorite New England Portside cities!
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So glad this was posted! I’m going to Portland in September with my sister and will definitely be using this guide, thank you!
That’s great– I hope you have an amazing trip! — Jess
I’ve been wanting to go to Portland, Maine. Thank you for this travel guide!
http://www.rdsobsessions.com
Of course, so glad that you enjoyed it! — Jess
The fresh seafood sounds incredible!
Some of the best in New England, in my opinion! 🙂 — Jess
My hometown! I think Fore Street is a little overrated, and the Streets have better restaurants – Street & Co, Scales, Standard Baking, etc. But if you can get a rez, I wouldn’t turn it down.
If you have access to a car, get off the peninsula! Go to Woodford F + B for mussels and fries, the Proper Cup for coffee (Tandem is also great on Congress!), Riverside for all of the breweries (Foundation, Austin Street, Allagash, et alia) and Tony’s Donuts (SO MUCH BETTER than Holy Donut; this is my hill to die on). Then walk/run Baxter Boulevard, accessible from the East End path, to burn off all that food.
You can even go over the Casco Bay Bridge to South Portland/Cape Elizabeth. Get bagels from Scratch, ice cream from Red’s, and then enjoy an Italian sandwich from Amatos at Fort Williams/Portland Head Light, the oldest Lighthouse on the Eastern Seaboard.
Love my city.
All great suggestions! Thanks for sharing! — Jess
I love Portland! I have a lot of family in Maine so I have been frequently. I absolutely love the restaurant, Duck Fat. Have you been to the restaurant, Central Provisions?
Jill
https://jilliancecilia.com/