Skip to Content

The Complete Tourist Walking Guide to Portland, Maine

The coastal city of Portland, Maine is a historic fishing village with a quaint modern charm. The downtown area of Portland offers an eclectic mix of an old port city combined with a modern artistic vibe. We found that the best way to experience Portland is to park your car and explore the city on foot. There are so many small boutiques and unique shops to explore that you would not want to miss out on.

Portland is only a 90 minute drive north of Boston and offers a seasonal Amtrak train for those looking for a car free adventure. To fully experience the city of Portland and all its offerings, we recommend visiting anywhere from a weekend getaway to the ultimate week of vacation. If you are looking to explore Maine beyond Portland, we also have a list of the best day trips Portland.

Tourist map to Downtown Portland

The best attractions in Portland, Maine

Waterfront along Commercial St.

Go for a stroll along the historic cobblestone roads of Commercial St along the waterfront. Along the road you can enjoy rows of beautiful brick architecture with plenty of interesting stores to take a peek into. Walking along the waterfront there are a handful of working piers that you can go down, including

Victoria Mansion

Take a guided tour of the Victoria Mansion with one of the most beautifully decorated interiors in the country. Stepping through the doors of this 19th century mansion feels like walking into a museum, but the works of art are painted directly on the walls and ceilings.

The tour of the Morse-Libby House offers a first hand perspective on the two families that occupied the mansion throughout its history. Guided tours are available daily from 10AM t0 3:45PM and tickets are $16 per adult.

Portland Museum of Art

The Portland Museum of Art not only holds a vast collection of local iconic artists but also American, European, and contemporary art. The museum holds a range of events throughout the week, so make sure to check if anything is going on during your visit. The coolest part of the Portland Museum of Art is thanks to private donations, it is free for everyone 21 and under!

Maine Historical Society and the Wadsworth-Longfellow House

Take a glimpse at the man behind the white beard and world renowned poetry. Head on over to the Maine Historical Society to sign up for a guided tour of the neighboring Wadsworth-Longfellow House. Guided tours are $15 per adult and only operate from May to October.

The most interesting thing about the Longfellow tour is learning about the vast diversity of the man before he became a legend. Many students grow up learning his words in Paul Revere’s Ride, but Lonfellow’s love of music and entertaining come to light in the design of his house. There is so much more to his legacy than this tour can explore.

Portland Observatory

Climb to the top of America’s last standing maritime signal tower. The Portland Observatory was built in 1807 to help manage Portland’s significant maritime movements. You can now climb to the top of this wooden tower for breathtaking panoramic views over the city of Portland and surrounding waters, Making your way though the interior of the tower you learn the history of the port city along with ideation and construction of the tower.

Eastern Promenade

Go for a stroll along the waterfront trails of the Eastern Promenade. This green park offers spectacular views of the harbor and ocean along with the closest beach to downtown Portland. If you are interested, cross over Tukey’s Bridge and complete the full loop trail around Back Cove.

Maine Narrow Gauge Railroad Co. & Museum

You can also explore this area of Portland with the The Maine Narrow Gauge Railroad Co. & Museum. Enjoy a half an hour train ride along the Eastern Promenade with plenty of historical information and context provided by the conductor.

Besides for the train ride, there is a small museum with more train cars and the complete history of these uniquely small width railroad lines. The Narrow Gauge Railroad Museum is open daily from May 5th to October 28th. The museum is open from 9:30 AM to 4PM with train rides running on the hour from 10AM to 3PM. Tickets are $5 per adult.

Save this article for later

The complete Tourist Walking Guide to Portland, Maine The complete Tourist Walking Guide to Portland, Maine

Sharing is caring!

← Previous
Road Trip Packing list: What items do I need for a road trip?
Next →
Complete Itinerary of What To Do in Buenos Aires in 3 Days