15 Fun Activities to do While in Portland, Maine

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Here is a list of things to do while you are in town for The Agents of Change Conference. Many of you are traveling to our little city and plan on staying a few days. If you can’t stay a few days after the conference, bookmark this for your NEXT trip to Portland, Maine because we just know you are going to fall in love with our city and want to come back! The list contains 15 fun things, in no particular order, to do while spending your time in Portland!

1) The Portland Science Center

The Portland Science Center’s exhibit is currently the “Titanic: The Artifact Exhibition”. You will get an exclusive look at 100 artifacts that were recovered with the Titanic when it was recovered. You will receive a replica boarding passes with exact features of what it looked like back in 1912. The Science Center is a cool place for people of all ages. Get your tickets for the Titanic exhibit today! 

2) The Maine Brew Bus

Ever wanted to tour a bunch of local breweries in Portland and not have to drive to each one? Well, The Brew Bus has you covered! Their tours consist of 3 local breweries, distilleries, and wineries in the city. Each tour has different stops, check out their website to choose your tour. They have been rated the #1 activity to do in Portland by Trip Advisor users, so whether you are a beer enthusiast or looking for something unique to do, The Maine Brew Bus will be sure to suit your needs.

The Maine Brew Bus

Photo Credit: The Maine Brew Bus Facebook Page


3) Farmer’s Market

The Farmer’s Market happens twice a week in Portland. On Wednesdays, the market is located in Monument Square and on Saturdays it is located in Deering Oaks park from 7am to 1pm. There are plenty of farms and local foods at the market, they’re so fresh that there is still dirt on most of the vegetables. Portland is a strong believer in “Buy Local”, there is no better way to buy local then to buy a bulk of your groceries at The Farmer’s Market. 

Farmer's Market Collage

Photo Credit: Portland Farmer’s Market


4) Portland Trails

Are you looking to experience the beauty of the city without walking through Downtown Portland? If so, Portland Trails has you covered! In total there are 70 miles of trails that span over Portland, South Portland, Westbrook, and Falmouth. There are many different trails depending on what you are interested in, including wooded areas such as Fore River Sanctuary or multi-purpose trails where you can run, walk, or bike such as Back Cove (Baxter Boulevard). These trails will definitely give you a scene of Greater Portland that you never knew was there. 

Photo Credit: Portland Trails Instagram Page

Photo Credit: Portland Trails Instagram Page


5) Foodie Tours

Calling all the foodies, we have just the tour for you. Maine Foodie Tours is based out of Portland but also has tours in Bar Harbor, Kennebunkport, and Rockland. These tours bring visitors to restaurants and cafes to show off Maine’s local samplings while being entertained by a very knowledgeable tour guide.  They currently have 35 5-star reviews on Yelp, and are a winner of the 2015 Leadership and Hospitality award presented by The Greater Portland Visitors and Convention Bureau.

Lobster Mac N' Cheese

Photo Credit: Maine Foodie Tours Instagram Page


6) Wine Wise Events

Is your knowledge of wine subpar? Let Erica Archer take you on a walking tour like no other. It is more than a wine tasting, Wine Wise takes people on a journey of where the wine came from, tells you how to pair food with the wines you try, and explains to you what makes them unique. Wine Wise not only offers walking tours but also “Wine Sails & Harbor Cruises” tours the scenic coastline and lighthouses while pairing a variety of wines with cheese. On AOC weekend, Erica has a wine walk exploring wines of the Mediterranean Saturday and a sail with European white wines and OYSTERS on Sunday! Those will sell out!

Wine + Sailing

Photo Credit: Wine Wise Events


7) Summer Feet Cycling

Summer Feet Cycling offer Maine day trips as well as bicycle tours throughout the state. Their day-trips consist of a half day guided bike tour throughout Portland where you can choose from 1 of their 3 signature tours: 5 lighthouse tour, bikes and brews tour, and the explore Casco Bay tour. If you are a more experienced rider and want to go out on one of their weekend or week-long tours that’s available too. We just know that it’s a great way to explore the great state of Maine, not to mention it’s great exercise!

Summer Feet Cycling

Photo Credit: Summer Feet Cycling Facebook


8) Portland Art Museum

The Portland Art Museum is a nice change of pace considering all the other fun activities on this page. Nestled in the Arts District in Portland, the museum has a wide range of holdings of American, European, and contemporary art. They also have a big collection of iconic pieces from Maine artists. During AOC week be sure to check out the new Tim Rollins and K.O.S. exhibit. It will be hard to miss the Portland Museum of Art due to the large “Seven” sculpture in front of the building!

Photo Credit: Portland Museum of Art’s Facebook Page


9) Portland Observatory

The Portland Observatory was built in 1807 while Captain Lemuel Moody ordered the construction of the 86-foot-high observatory.  It was a communication tower to allow ship owners to know when their ships were arriving in the harbor. This historical landmark is a hidden (pun intended) gem in Portland. There are plenty of tours daily but we suggest going during their sunset tour, where you can watch the sun set from the top of Portland Observatory. It’s a must see. The top makes for great views and Instagram photos! Don’t worry we won’t spoil it, you’ll have to see it for yourself! 

Portland Observatory

Photo Credit: Portland Landmarks Facebook Page


10) Casco Bay Lines and Islands

In the Casco Bay there are eight gorgeous islands that you can visit by ferry on Casco Bay Lines. They also offer several types of cruises. Their Scenic cruises include, the Mailboat Run, Diamond Pass Run, Sunset Run, and Sunrise on the Bay. Sometimes Casco Bay Lines offers Music Cruises which includes many local performers, a meal, and a cash bar! If you wanted to spend the day on one of the eight islands, Casco Bay Lines can get you there!

Casco Bay Lines

Photo Credit: Casco Bay Lines Facebook Page


11) Portland Head Light

One of the most iconic photos found on Instagram is of Portland Head Light situated just fifteen minutes outside of Portland. The lighthouse that was commissioned to be built by George Washington and helped immensely during The Civil War. This historic and oldest lighthouse in the state of Maine is worth the Instagram post alone. 

Portland Head Light

Photo Credit: Carrie M.


12) Old Port District

One of the most notable places for visitors to frequent is Portland’s Old Port district. There is plenty to explore in the downtown district, with all of the locally owned shops, bars, and restaurants. Everywhere you turn there will be a unique place for you to explore and the best part is that they are all so close together. If you are planning on an extended stay, we suggest planning at least an entire day in the Old Port. 

Downtown Portland

Photo Credit: Portland Downtown’s Facebook Page


13) Freeport U.S.A.

Another great shopping/eating area is Freeport, known as one of two shopping outlet hubs in Maine. Here you will find a variety of outlet stores as well as the iconic L.L. Bean boot and the L.L. Bean flagship store open 24/7 365 days a year. There are plenty of great local foodie spots as well! Freeport is also another day trip due to all the shopping that you can do at the outlets.

Downtown Freeport

Photo Credit: Freeport U.S.A.


14) Victoria Mansion

Want to visit one of the oldest buildings in Portland and feel very elegant at the same time?  The Victoria Mansion is the place for you! The Victoria Mansion was built between 1858 and 1860 for Ruggles Sylvester Morse who was a proprietor in New Orleans of luxury hotels. The mansion has about 90% of its original furnishings that are still in place. It is 2016, these furnishings are over 150 years old!

Photo Credit: Victoria Mansion


15) Duck Tours

Want to learn about Portland’s history while traveling by road and sea?! Well Downeast Duck Tours has you covered! This tour will take you to all the points of interest while giving you fun facts and secrets about the great city of Portland. You will then drive into the ocean and tour the working waterfront by sea, and who knows maybe you’ll meet a few sea friends along the way!

Photo Credit: Downeast Duck Adventures


There you have it, a starters list for fun things to do in the Greater Portland area! Trust us, we know that we missed several places! Where is your favorite activity to do? Tell us in the comments below!

Have you had your fun and are now hungry? Check out our list of 20 best restaurants in Portland and make sure to make your reservations!