How to Spend the Perfect Weekend in Portland Maine (2023)

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Latest posts by Katie McAleer (see all)

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. Also check out these top places to stay in Portland, including boutique hotels!

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 Portland ME weekend getaway by planning ahead!

Whether you are going for a Portland Maine girls trip, 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 Maine! 

Enjoying the Perfect Weekend in Portland Maine

Go on a Food Crawl

Portland is a foodie paradise and 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 Portland ME 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 sometime during your Portland Maine weekend.

Read Next: 7 Spots for the Best Breakfast in Portland Maine

Several boats in the water next to a dock
This could be your view, too, during your Portland Maine weekend!

Fuel Up at one of Portland’s Top Coffee Shops

You’ve got a lot to see and a lot to do during your weekend in Portland Maine, better fuel up at one of Portland’s best coffee shops. You’ve got some great options, too, because just as this city takes its food and craft beer seriously, it does the same with its coffee!

Hopefully you’ll have time to check out more than just one, but if you’re looking for a quick recommendation, consider Tandem, the downtown Portland vintage gas station turned coffee shop that is just as aesthetically pleasing to the eye as its coffee and baked goods are to the palate!

Read Next: 11 Fun & Free Things to do in Portland Maine

Check out Portland Brewery Tours and Beer Tastings

Calling all craft beer lovers, Portland Maine 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, a perfect thing to do for your weekend in Portland Maine! This is a great option if you have a larger group.

A close up of a beer glass on a table
A weekend in Portland Maine is not complete without a stop by at least one brewery!

Explore Portland’s History and Heritage:

Portland was first settled in 1632 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; this is always one of the best things to do in Portland Maine.

Read Next: 7 Beautiful Lighthouses in Portland Maine

A rocky shore next to a body of water with a lighthouse and lightkeepers house in the distance
Portland Head Light should definitely be included in your Portland Maine 2 day itinerary.

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. This is a fun thing to do in any weather, but definitely should be on the list of things to do in Portland Maine while raining; can’t control the weather, but we can definitely control how much fun we have while it’s acting up!

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.

Read Next: 11 Irresistible Bakeries in Portland Maine


People walking on the sidewalk in front of buildings on Wharf Street in Maine
A weekend in Portland Maine could be just what you need!

Where to Stay During your Weekend in Portland:

Portland has really built up the last several years, from cute boutique hotels to the tried and true Hotel brands you know and love. I always like staying in Old Port because it is 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 during your weekend in Portland, Maine? You’ve got options.

Portland ME Vacation Rentals

If you want to live like a local during your Portland ME weekend, check out this list of 8 Awesome Portland Airbnbs, otherwise you might be interested in some of the Portland ME hotels below!

Portland ME Hotels

Blind Tiger Portland- 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!

Didn’t find your perfect place to stay during your Portland Maine weekend getaway? Check out more of the top Portland hotels here!

Have fun planning your Portland Maine weekend, and if you’re looking for other Maine weekend getaway ideas, we’ve got those too!

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