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Uncover the Old Port's deeper past—where sailors, merchants, immigrants, and reformers all left their mark.

Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of sailors, reformers, and immigrants. Learn about the Portland Freedom Trail, which honors the city’s fight for freedom and civil rights. The tour showcases the Old Port’s architectural charm and its transformation from a bustling shipping hub to a cultural center. Experience the tales of resilience embedded in its streets, from the Great Fire of 1866 to the revitalization efforts of the 1970s. Join fellow history enthusiasts for a memorable journey through Portland’s past and present. — Explore the historic Old Port district, a cultural and commercial hub — Walk along the Portland Freedom Trail, learning about civil rights — Discover stories of resilience, fire, and maritime life — Ideal for history lovers and those curious about Portland's heritage

Self-Guided Audio Tour of Portland’s Historic Old Port District

2 hours to 2 hours 30 minutesFree Cancellation

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The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

1 hour 45 minutesFree Cancellation

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Portland, Maine: Hidden Histories Guided Walking Tour

With this small-group walking tour, you'll go beyond lobsters and lighthouses and get a look at the true Portland, Maine—across 400 years of history. Meander downtown and the Old Port, visiting hidden landmarks and learning about Wabanaki leaders and other people and events left out of the history books. Discover centuries of destruction, revival, underrepresented perspectives, and other elements that mainstream tours gloss over.

Portland, Maine: Hidden Histories Guided Walking Tour

2 hoursFree Cancellation

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Desert of Maine - Wander in Wonder and Mini Golf Combo

Discover the fascinating Desert of Maine, a unique ecological wonder nestled in the lush pine forests of Freeport. This general admission and mini golf combo ticket grants you access to acres of rolling sand dunes, rich history, engaging exhibits, and mini golf. Explore the Tuttle Farmhouse interactive museum, embark on a self-guided ecology tour, and enjoy activities like a scavenger hunt. The Desert of Maine not only offers a glimpse into geological processes but also provides a fun-filled day of adventure for families and curious travelers alike. Come uncover the stories of this century-old attraction today.

Desert of Maine - Wander in Wonder and Mini Golf Combo

1 to 3 hoursFree Cancellation

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A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

2 hoursFree Cancellation

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Portland, Maine: Black History Guided Walking Tour

Maine's Black community is small, but its history here goes back more than 400 years. On this guided tour, you’ll dive deep into Portland’s Black history, discovering how this community—national leaders, laborers, skilled workers, activists, and more—fought for freedom and equality and defined the state's path. From Frederick Douglass to lesser-known Black Yankees, there’s far more here than meets the eye, and with this tour, you’ll learn all about it.

Portland, Maine: Black History Guided Walking Tour

2 hoursFree Cancellation

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Old Port Culinary Walking Tour from Portland

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Old Port Culinary Walking Tour from Portland

3 hoursFree Cancellation

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Private Portland to Cape Ann, MA Castles & Coast

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.

Private Portland to Cape Ann, MA Castles & Coast

8 to 10 hoursFree Cancellation

Must-Dos in Portland

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The Portland Head Light standing on the rock during sunset.

Portland Head Light

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The Ram Island Ledge Light in Casco Bay on a cloudy day.

Casco Bay

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Fort Gorges rising up from the surface of Portland Harbor.

Fort Gorges

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Eastern Promenade

Eastern Promenade

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