Updated November 2018
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Portland, Maine is one of the East Coast’s most visited seaports, and the largest city in the state of Maine. Aside from its beautiful setting on Casco Bay, it has a vibrant small city culture feel, full of good restaurants, museums, galleries, and shopping. There are so many fun things to do in Portland, Maine.
With cobblestone streets, red brick warehouse buildings, Victorian houses, and a bustling waterfront, this city by the sea is a popular New England summer destination. There are parks and green space along the water, biking and walking trails, and fishermen out and about, making it a place where nature truly meets city culture. Whether you’re into the outdoors, the arts or excellent food, Portland has something for everyone.
Families as much as hipsters enjoy visiting Portland, and it can be a destination in and of itself, or a stop on the way up to northern Maine, which is what we did. Note, it’s extremely popular in the summer months and hotels book up quickly. I highly recommend staying in the Old Port district by the water, or the Arts district on Congress Street toward the middle of the city, where you can easily walk around from place to place.
Fun Things to do in Portland, Maine
Fun things to do in Portland: Walk Around Old Port
Portland’s waterfront, Old Port, is where you will discover the fishing piers, cobblestone streets and the famous red brick warehouses that so define Portland. Commercial Street is the main street here filled with old-school ice cream shops, pubs and restaurants; walk a little inland a few more streets, and the action continues with all sorts of wacky Maine trinket shops, eateries and cafes and bars loaded with artisanal food and beer. Make sure to stop in at Standard Bakery, a Portland institution.
Old Port is of course great during the day – watching the fishermen and boats at dock – but also a lot of fun at night. It’s known as the nightlife district. If you’re an early bird or have kids, no problem, it’s still hopping earlier on, with restaurants in full swing, and live music bellowing in the distance.
You might also enjoy: Acadia National Park: Best Things to do with the Kids
Fun things to do in Portland: Explore the Eastern Promenade
The Eastern Promendade is a stunning 1.5 mile public park along the water in the neighborhood of Munjoy Hill, east of Downtown. Designed by the Olmstead Brothers, it’s comprised of 68 acres of land filled with recreational facilities, a 2 mile long paved trail good for walking and biking, sports fields, East End Beach, and a marvelous playground overlooking the sea. We took our kids to the playground while we enjoyed a coffee from one of the uber cool food trucks located here, as well as a beautiful view of the bay.
Fun things to do in Portland: Go for a ride along the Maine Narrow Gauge Railroad
Also located in the Eastern Promenade is the Maine Narrow Gauge Railroad Museum. Dedicated to the preservation and operation of Maine’s two foot gauge railway equipment, there are exhibits, historical rail cars, childrens’ activities, and of course, a scenic waterfront train ride. Great fun for the kids, the train takes you along the Casco Bay and lasts 40 minutes.
Fun things to do in Portland: Climb The Portland Observatory
For fantastic views of Portland and the harbor, climb 7 stories to the top of the historic Portland Observatory – the oldest maritime signal tower in the country. Go back in time and be on the lookout for anything amiss in the distance. My girls held up well, thanks to their Champion sneakers, which never fail!
You might also enjoy: A Guide to Bar Harbor, Maine
Fun things to do in Portland: Visit one of Portland’s Museums
The Portland Art Museum has an impressive collection of art works dating from the 18th century to the present, including works by artists Winslow Homer, Andrew Wyeth and Marsden Hartley. Great for a rainy day, this museum has family activities as well.
International Cryptozoology Museum
Cryptozoology is the study of hidden or unknown animals, such as Big Foot. We didn’t make it to this, but have definitely earmarked it for next time! Sounds totally unique and right up my girls’ alley.
Children’s Museum & Theatre of Maine
Learn about all things Maine at this incredibly popular children’s museum where you can do things like climb aboard a shipwreck or explore the nationally recognized Camera Obscura.
Perhaps not listed in many of the kids’ sections in the guide books, but we stumbled upon this museum in the waterfront, where we finally saw the traveling “Titanic: The Artifact Exhibition”. I have always wanted to see this! A bit obsessed with the Titanic, as I had a relative on it – a great, great uncle – who not only survived after being in the freezing water, but was told he would have to have a leg amputated due to gangrene. He was obstinate in not having the surgery and walked around for two days straight to try and get the circulation back – and not only did he do that and beat the gangrene against all odds, but he later went on to win the Wimbledon and U.S. Open Championships! An amazing and inspirational story. His name was Richard Williams II. At the beginning of the self-guided tour you receive a passenger ticket with the name of the real person who was aboard the Titanic – I asked for his and got it, as seen in the photo above.
Fun things to do in Portland: Visit the Portland Headlight in Fort Williams Park
Located in Cape Elizabeth just outside of Portland, the Portland Head Light is the oldest lighthouse in Maine. Beautifully set on the coast of Fort Williams Park, visiting this lighthouse will fulfill all your classic Maine coastal image needs – the rocky shores are exactly what you think of when you think of Maine. The Museum at Portland Head Light is an award-winning museum and is kept in the Keepers’ Quarters.
Fort Williams Park is 90 acres worth of fields, walking trails and majestic views of the coast. You could spend a long time here, walking around and picnicking and exploring the beauty and serenity of the area. Note it does get crowded with tour buses pulling up non-stop, so best to visit as early in the day as possible.
You might also enjoy: A Guide to Boothbay Harbor, Maine.
Exploring more of Coastal Maine? Check out the guidebook below. I love Moon!
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pretty! #mondayescapes
Looks fantastic. We’ve been to Maine, but never Portland.
Author
Portland is cool – and a great culinary scene, which you guys would like.
Author
Thanks:)
Stunning Corey – those blue skies and beautiful pictures make me want to escape to Portland right now!! I love the sound of the old port – anywhere with fishermen and boats always gets my vote.
Author
Me too, Joy:)
Fantastic photos! Portland looks our type of place! I love the fact it’s fashionable and family friendly too
Author
Thanks Ting – I need to hop on over to your blog – hope you’re feeling well!
What a stunning place – quaint AND full of museums. Sounds right up my street (and, like you, I’m intrigued by the museum of cryptology….’
Author
I know, I’ve never heard of such a thing..wish we had time to check it out!
What an amazing personal link to have with the Titanic and such an incredible story. I love that they let you have his ticket too. Gorgeous waterfront as well, looks a fab place to wander. #citytripping
Author
Thanks! I’ve been wanting to see the Titanic traveling exhibition for some time and seemed like fate that it was right there as we walked by;).
I would very much like to explore the Portland observatory and the views of the Portland Highlight in Fort Williams park look lovely.
Author
Thanks for reading – yes, incredible views at those two places, highly recommend.
So many great stories here as well as your gorgeous photos, Corey. I just love the story of your Titanic relative. What an inspiration! Thanks so much for taking me on a tour of Portland and for linking it up to #FarawayFiles
Author
Thanks Clare – I know, it’s such an inspirational story. I’m an avid tennis player myself but have been out of the game since my knee surgery (soon to get back out on the court again, hopefully), and whenever I get down I think of that story, because really, it could be a whole lot worse!
I’m a big fan of coastal towns. I love the waterfront and the history. Portland’s looks like a wonderful place to explore. Thanks so much for linking with #MondayEscapes
Author
Thanks Clair – and for hosting:)
What a fantastic story about your great great uncle, I’d be very proud to have him as a relative! Just learnt something new from reading your post too – I’d never realised the meaning of cryptozoology before 🙂 #Mondayescapes
Author
Ha – I know, I hadn’t known either! Quite fascinated..
My goodness – Portland sounds amazing! Great food, beach, a lighthouse AND train ride! We’d love it there! Thanks for putting it on my radar and for linking #citytripping
Author
Yes, it seems to have it all. Thanks as always for hosting:).
You made me wonder if I can no longer be a hipster if I have a family Corey! Ha – don’t worry I could never be mistaken for a hipster but it’s good to know that if I could Portland, Maine is the place for me. Jokes aside, my son and hubby saw the railway and are itching to go. I love lighthouses and the one pictured looks like a perfect New England example. Thanks for sharing beautiful Portland on #FarawayFiles
Author
Haha, Katy..I really should switch the wording around..of course you can still be a hipster and a mom at the same time! Everyone in Brooklyn is! Have a great weekend:).
What a great story about your great great uncle!! I love him too now, purely for his sheer determination to keep his leg – what a guy!!!!!! Seriously, I am telling somebody this story tomorrow whether they like it or not! #citytripping
Author
Love it! I’ll never forget when soon after the Titanic movie came out in the 90’s, I was at a Christmas party telling some people the story and before I knew it the entire party was circled around me, music stopped…everyone loves this story!!
It all looks so pretty and I think I’d had loved a go on that train to see loads. It makes sense now that it’s got multiple lighthouses too…with it being a port, not something I thought of before (doh!). Definitely a lovely looking place to see one day! #mondayescapes
Oh and just have to say, what a guy your uncle was, so glad he got the feeling back in his leg!!
Author
Thanks! I know it’s quite a story. Thanks for reading!
I love Portland. I haven’t been in years and should really revisit. You have great tips! #farawayfiles
Author
Thanks – and thanks for stopping by:).
Ok – so as an Oregon Girl from the west coast PORTLAND – I see remarkable similarities and had to chuckle about the following “… Whether you’re into the outdoors, the arts or excellent food, Portland has something for everyone. Families as much as hipsters enjoy visiting Portland…” which could have as easily been written about MY Portland. 😉 I love the New Englandness of Maine’s port town and those lighthouses you would NOT find in Oregon. Adorable, charming and on my must visit list! Thanks for linking with #FarawayFiles! Cheers, Erin
Author
Hahaha – so true – I def think of hipsters when I thinking of Portland, OR!!! They indeed seem like incredibly similar cities. I’ve always wanted to visit your Portland, maybe one of these years when I go out to visit my brother in Seattle;).
Both excellent towns close to my heart! I went to college and met my husband in Seattle!
Author
Nice! My brother met his wife at grad school in Seattle..so now I have Sleepless in Seattle on my brain haha..
Appropriately so! But if you have lived there you will realize how many “liberties” that movie took with where things are exactly in Seattle. Still awesome. Cheers from Copenhagen!
Wow – how incredible was your great uncle! What an inspirational story.
Author
I know! Thanks Nell.