10 Things to Do in Portland Maine That Will Make Your Trip Unforgettable

By jhenr | Updated October 27th, 2022

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If you’ve ever wanted to visit Portland Maine, but aren’t sure where to go or what to do, you’re not alone. This New England city has plenty of restaurants, bars, and attractions that will make your trip unforgettable. Here are 10 things to do in Portland Maine that will give you the experience of a lifetime.

Walk the Casco Bay Islands

PORTLAND, ME -10 OCT 2020- View of a ferryboat from the Casco Bay Island Ferry service in the Portland harbor, Casco Bay, Maine, United States.

One of the best things you can do with your time here is head out on the Casco Bay Islands. The Casco Bay Islands (or Casco Bay, for short) are a group of islands off the coast of Southern Maine that make up a UNESCO World Heritage Site. There are more than 20 islands, each one with its own personality and allure. My favorite is Long Island, which has the most sandy beaches and beautiful views of Portland Harbor.

Bike Around Back Cove

Portland, Maine, USA coastal townscape.

Portland is known for being one of the most bike-friendly cities in America, and this ride will show you why. From historic waterfronts to picturesque bridges, you won’t believe how much there is to see while biking around Back Cove. It’s one of the best ways to experience all of Portland!

Take a Drive up Route 1

Highway 1 on the pacific coast, California.

If you’re looking for a quieter, more scenic route, take Route 1 up the coast. The drive can be as short as an hour or as long as five hours, depending on your destination. It’s well worth taking some time to explore the coastline and enjoy a slower pace of life than what you’ll find in nearby towns.

Maine is one of those places that has something for everyone.

Walk the Eastern Promenade

Eastern Promenade in Portland, Maine

One of the most beautiful walking paths in Portland is the Eastern Promenade, which starts at Eastern Promenade Park on Commercial Street and winds along the Fore River. Along this path you’ll find spectacular views of Casco Bay and Fort Gorges and glimpse what life was like for local sailors a century ago. It’s also a great spot for bird watchers, as there are many species of birds that live here year round.

Stroll through The Public Market

fast food of burgers french fries and ketchup on a dark background

A great place to start is The Public Market, which is a foodie’s dream come true. You’ll be able to sample everything from the best coffee and beer, all the way down to some of the finest chocolate you’ve ever had. There are also plenty of restaurants and shops nearby that will make your visit well worth it.

Visit The Rose Gardens

Fount in the Portland Rose Garden

The roses at The Rose Gardens in Portland, Maine are one of the most popular sights. They’re breathtaking and the perfect size for photo ops. You can find these beauties on the Eastern Promenade right next to Deering Oaks Park. The gardens are open from sunrise until sunset and admission is free!

Exchange Street

Fresh organic produce on sale at the local farmers market.

Portland is a great place to shop and Exchange Street has plenty of options for you. One of the best is Saturday Market where you’ll find handmade items like jewelry, clothes, pottery, and more. If you’re looking for something more traditional, there are also boutiques like J.Crew and Anthropologie that are worth checking out.

Portland Art Museum

PORTLAND, OR – MARCH 24, 2012: Portland Art Museum sign outside the well known brick building in downtown Portland, Oregon.

Located downtown, the Portland Art Museum is a must-see. The museum’s permanent collection includes the largest public collection of works by Henry Ossawa Tanner and Edgar Degas outside of Paris, France. The exhibits change often, so be sure to stop by often or purchase a membership for year-round access.

The museum also features an impressive temporary exhibit on its rooftop every summer, which provides a nice view of the city below.

Explore The Old Port District

Istanbul, Turkey – March 09, 2021 : Beykoz District street view in Istanbul

The Old Port district is the heart of downtown Portland and it’s where you’ll find all the best shops, restaurants, and bars. The best way to see it all is by walking or biking along the waterfront.

Start at Fort Williams Park, which overlooks Casco Bay and offers stunning views of Portland’s skyline. The park is also home to a historic fort from 1808 and hosts several summer concerts. After you’ve explored the park, make your way down Commercial Street and head north on Fore Street. You’ll find tons of unique shops, boutiques, cafes, and restaurants that you can explore at your leisure. One of my favorite spots is a pizzeria called Pepe’s on Fore Street—the best pizza in town!

Take a Ferry to Peaks Island

PEAKS ISLAND, ME -12 OCT 2020- View of the Peaks Island terminal from the Casco Bay Island Ferry service in the Portland harbor, Casco Bay, Maine, United States.

If you’re looking for a different way to explore the world, consider taking a ferry ride over to Peaks Island. This quaint little island is one of the most scenic places in all of Maine and it’s just waiting for you. You’ll be able to find great restaurants, shops, and so much more while here. The best part is that it only takes fifteen minutes by boat!

Visiting Peaks Island is like escaping from the world for a little bit.


Portland is a gem of a city and offers visitors so much to do. From exploring the Portland Head Light to indulging in all things lobster, you’re sure to have an unforgettable trip if you use our guide of 10 things to do while in Portland. So what are you waiting for? Start planning your getaway to Portland, Maine today!