Fun Things to do in Portland, Maine

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.

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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.

Booking.com

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!

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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

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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