Fun Things to do in Portland, Maine

Fun Things to do in Portland, Maine

Updated November 2018

This article may contain compensated links. You can read more about our full disclosure here.

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

Fun things to do in Portland Maine includes going to the waterfront.

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 Promenade is a fun thing to do in Portland, Maine

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

Climbing the observatory in Portland, Maine

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

Portland Museum of Art

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.

Portland Science Center

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

Fun things to do in Portland, Maine includes a visit to the Portland Headlight.

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!


Disclaimer: Fifi + Hop is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to,, Amazon and the Amazon logo are trademarks of, Inc. or its affiliates.

Enjoy this post and want to save it or share with others? PIN IT!

Fun things to do in Portland, Maine




  1. October 17, 2016 / 1:19 pm

    pretty! #mondayescapes

    • Lyn Cook
      October 17, 2016 / 5:23 pm

      Looks fantastic. We’ve been to Maine, but never Portland.

      • October 17, 2016 / 6:36 pm

        Portland is cool – and a great culinary scene, which you guys would like.

  2. October 18, 2016 / 9:48 am

    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.

  3. October 18, 2016 / 9:19 pm

    Fantastic photos! Portland looks our type of place! I love the fact it’s fashionable and family friendly too

    • October 19, 2016 / 1:36 am

      Thanks Ting – I need to hop on over to your blog – hope you’re feeling well!

  4. pigeonpairandme
    October 19, 2016 / 11:13 am

    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….’

    • October 20, 2016 / 2:20 pm

      I know, I’ve never heard of such a thing..wish we had time to check it out!

  5. October 19, 2016 / 10:06 pm

    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

    • October 20, 2016 / 2:22 pm

      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;).

  6. October 20, 2016 / 1:03 pm

    I would very much like to explore the Portland observatory and the views of the Portland Highlight in Fort Williams park look lovely.

    • October 20, 2016 / 2:23 pm

      Thanks for reading – yes, incredible views at those two places, highly recommend.

  7. Clare Thomson
    October 20, 2016 / 1:15 pm

    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

    • October 20, 2016 / 2:26 pm

      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!

  8. October 20, 2016 / 1:30 pm

    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

    • October 21, 2016 / 6:10 pm

      Thanks Clair – and for hosting:)

  9. afamilydayout
    October 20, 2016 / 2:49 pm

    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

    • October 21, 2016 / 6:11 pm

      Ha – I know, I hadn’t known either! Quite fascinated..

  10. October 20, 2016 / 4:42 pm

    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

    • October 21, 2016 / 6:12 pm

      Yes, it seems to have it all. Thanks as always for hosting:).

  11. October 20, 2016 / 7:28 pm

    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

    • October 21, 2016 / 6:14 pm

      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:).

  12. October 20, 2016 / 9:31 pm

    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

    • October 21, 2016 / 6:17 pm

      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!!

  13. October 21, 2016 / 5:56 am

    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

  14. October 21, 2016 / 6:00 am

    Oh and just have to say, what a guy your uncle was, so glad he got the feeling back in his leg!!

    • October 23, 2016 / 2:42 am

      Thanks! I know it’s quite a story. Thanks for reading!

  15. October 21, 2016 / 4:59 pm

    I love Portland. I haven’t been in years and should really revisit. You have great tips! #farawayfiles

    • October 23, 2016 / 2:42 am

      Thanks – and thanks for stopping by:).

  16. October 25, 2016 / 5:38 pm

    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

    • October 26, 2016 / 3:00 pm

      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;).

      • October 26, 2016 / 3:02 pm

        Both excellent towns close to my heart! I went to college and met my husband in Seattle!

        • October 26, 2016 / 3:04 pm

          Nice! My brother met his wife at grad school in now I have Sleepless in Seattle on my brain haha..

          • October 26, 2016 / 3:07 pm

            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!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.