How to Spend the Perfect Weekend in Portland Maine

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Planning a weekend trip to Maine’s biggest city? Don’t miss these top things to do, so you can have the perfect weekend in Portland, Maine.

Growing up in the Boston area I have always been so grateful to be able to explore New England; you can be on the beach one day and up in the mountains the next.

New England is full of charming little towns, bustling cities, and cozy beach resorts. Through my blog Katie From Boston, I have been able to travel to almost every corner of New England trying restaurants, hotels, and all the fun activities from Woodstock Vermont, to Nantucket!

Just over 2 hours from Boston, Portland Maine is one of my favorite weekend getaways. With lots to do, see, and eat there is a little something for everyone. Make the most of your New England weekend getaway by planning ahead!

Whether you are there for a girl’s weekend, a couple’s getaway, a day trip, or are looking for something more family-friendly, my favorite time to go is the fall; it is still warm enough to do all the outdoor activities, but the summer crowds are gone. If you’re going in the winter or if it’s a rainy weekend be sure to plan out some indoor activities. Below are all my recommendations on the best things to do in Portland! 

Visiting Maine? You may also want to check out the top things to do in Acadia National Park (and our 3 day Acadia itinerary) and the best things to do in Rockland, Maine.

Enjoying the Perfect Weekend in Portland Maine

Go on a Food Crawl

Portland is a foodie paradise, I love trying new restaurants every time I am in town, but there are a few spots you must try if you’re only in town for the weekend! You’ll find everything to creative, inventive menus and classic seafood menus featuring all your favorites from lobster rolls to clam chowder! Consider taking a highly-rated guided food tour, or go explore these great spots on your own:

Duckfat– Known for their Poutine Duckfat is a Portland staple. Get a Panini and an Original Duckfat Milkshake! I come back to Duckfat every time I am in Portland, there is often a wait so be ready for that but trust me that Poutine is so worth it!  

Central Provisions– Located right in the center of Old Port this cool spot has an open kitchen, last time I was there we sat at the bar and got to watch all the chefs at work. The Bone Marrow Toast is a must-try.

Solo Italiano– Amazing pasta, their menu changes daily so no matter how many times you go back you will always find something new to love. I typically lean towards seafood when I am in Portland but especially when it is cold out this cozy Italian spot is just what you need!

High Roller Lobster– Calling all lobster roll lovers! Get a classic lobster roll or go for my personal favorite, the Lobster Cheese Crisp Taco, get it with the Jalapeno mayo! Located right in Old Port its perfect place to stop for lunch. 

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A sunset view of downtown and the harbor in Portland, Maine

Check out Brewery Tours and Beer Tastings

Calling all craft beer lovers, Portland is full of micro-breweries! Plan out your day and hit up some of Portland’s best breweries

Allagash Just a short drive from downtown Portland Allagash is worth the drive! Take a tour of the brewery and then do a tasting, they offer flights of 4 if you want to try a few different beers! There is a small food menu, mainly sandwiches but you should definitely get the lobster roll! 

Shipyard Located right on the Portland waterfront the Shipyard tasting room is a must-visit.  Beers are constantly rotating with seasonal offerings so no matter how many time you visit Portland you can stop by for something new and exciting!

Rising Tide– One of my personal favorites, Rising Tide has a seasonal patio complete with corn hole! You can take a tour of the production and then enjoy a tasting. They also offer wine, cider, and some non-alcoholic beverages if not everyone in your group loves beer. 

Oxbow Blending and Bottling– The best part of Oxbow is that there share a beer garden with Duckfat. They also house Gallery 49, an art gallery featuring local artists. Try a variety of beers, have some amazing food, and take in the local art all at one stop! 

Maine Brew Bus– Why choose one when you can check out a whole bunch! The Maine Brew Bus will take you on a tour of some of the best breweries. I highly recommend the Local Pour Tour that runs on Saturdays. This is a great option if you have a larger group.


Explore Portland’s History and Heritage:

Portland was first settled in 1632, it is the largest city in Maine and has historically been an extremely important seaport! There are so many options when it comes to exploring Portland, you can take in the history, the waterfront, and get active! 

Portland Head Light

If the weather is nice, take a ride to Portland Head Light, technically in Cape Elizabeth, it’s just 9 miles south of Portland. It is one of the most photographed lighthouses in the US for a reason, it is beautiful! Bring some snacks, a camera, and walk along the beach!

Read Next: 5 Beautiful Lighthouses in Portland Maine

Portland Head lighthouse with the rocky coastline in the foreground. Portland, Maine, United States.

Shopping in Old Port

Stroll down cobblestone streets and pop in and out of tons of adorable boutique shops. The oldest part of the city, there are tons of great restaurants in this neighborhood for you to stop at for lunch. When you are all shopped out, stroll along the waterfront and take in the active, working wharf. 

Portland Museum of Art

If you’re visiting Maine during the colder months and need to get indoors for a while check out Portland Museum of Art. Admission is just $18 and allows you to take in all of the amazing exhibits! 

Mail Boat Tour

Did you know a ferry boat delivers mail to the various islands in Casco Bay? Better yet you can hop on and cruise Casco Bay. One of the oldest running services of its kind you can learn a lot about this history of Portland and Casco Bay. The views alone are worth it, pack a cooler and enjoy! 

Also check out these other options for how to get out on the water in Portland.

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Wharf Street, a cobblestone street in Portland, Maine

Where to Stay in Portland:

Portland has really built up the last 5 years, from cute boutique hotels to the tried and true Hotel brands you know and love. I always like staying in Old Port, it close to a lot of great restaurants, shopping, and has great views of the waterfront. Portland is pretty walkable in the Old Port and Waterfront area but if you’re not staying right in the Old Port area I would recommend bringing a car. There are also tons of ride-sharing apps active in the city so you should have no problem getting around no matter where you stay!

Wondering about the best places to stay in Portland, Maine? Here they are:

12 Awesome Portland Airbnbs

The Danforth– owned by Lark Hotels this adorable boutique inn is located conveniently in downtown Portland. Breakfast is included in your stay so fuel up for the day before exploring the city! Click here to check prices & book!

The Press Hotel– located right in Old Port this luxurious hotel is perfect for those looking to treat themselves. The Union located right in the hotel is an amazing restaurant! Click here to check prices & book!

The Westin Portland Harborview– close to everything you want to do and views that can’t be beat! The Westin is convenient and comes with all the amenities you could need or want! Click here to check prices & book!

Portland Harbor Hotel– the nautical design of this hotel goes perfectly with the harbor views! Right in Old Port, The Portland Harbor Hotel has Blue Fin North Atlantic Restaurant right in the hotel, perfect for grabbing a quick meal before you head out for the day. Click here to check prices & book!

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