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Commercial Street
Pass by
We start at historic Commercial Street, the heart of Portland's working waterfront. See original cobblestone and brick that was laid in the 1850s.
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United States Custom House
Pass by
See one of the most beautiful granite buildings in all of Portland.
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Fort Allen Park
Pass by
We'll drive through Fort Allen Park and get a majestic view of Casco Bay and its Calendar Islands. Also get up close views of memorials from the Civil War, Spanish American War, and WWII located in the park.
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Eastern Promenade Trail
Pass by
You'll see the Victorian era homes once owned by sea captains and merchants that line the Eastern Promenade, as well as Eastern Promenade Park which offers endless views of Casco Bay, islands, and forts.
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Portland Observatory
Pass by
We'll get a great view of the only remaining maritime signal tower in the U.S.
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Eastern Cemetery
Pass by
Hear about the legends and lore regarding the oldest cemetery in Portland, first established in 1668.
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Congress Street
Pass by
One of the busiest streets in all of Maine, we'll see Portland's eclectic downtown, Monument Square, and arts district.
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The Cathedral Of The Immaculate Conception
Pass by
The neo-Gothic architecture of this cathedral built in 1869 dominates the skyline of Portland.
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The First Parish Portland Unitarian Universalist
Pass by
This church is the oldest in Portland, and you'll learn about its rich history.
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The Wadsworth-Longfellow House
Pass by
See the home where Henry Wadsworth-Longfellow grew up and wrote his early poetry.
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Arts District
Pass by
We'll tour the center of downtown Portland, and its highly acclaimed Arts District.
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Portland Museum of Art
Pass by
See one of the finest art museums in New England, and learn about its exhibits.
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One Longfellow Square
Pass by
See the statue of Henry Wadsworth Longfellow, born in Portland in 1807.
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Victoria Mansion
Pass by
Get an up close view of the Victoria Mansion, the finest example in the country of a 19th century Italianate brownstone.
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Fort Williams Park
Pass by
We enter one of the most beautiful parks in the state, Fort Williams Park, and drive to Portland Head Light (located in the park) where you will be let off to explore.
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Portland Head Light
20m
This iconic lighthouse located within Fort Williams Park is the most photographed lighthouse in the country. Walk right up to the lighthouse, explore Fort Williams Park, and take in the views of Maine's rugged, rocky coastline.
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Fort Preble
5m
Get an up close view of Fort Preble (one of the oldest forts in Casco Bay) and learn about its storied history.
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Spring Point Ledge Lighthouse
5m
Get out for a photo of Spring Point Ledge Lighthouse, and its 900 foot long breakwater connecting it to the shore.
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Bug Light Park
Pass by
Enjoy panoramic views of the Portland skyline from this beautiful park that sits directly across the bay from Portland.
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Liberty Ship Memorial
Pass by
Get an up close view of the Liberty Ship Memorial, and learn about the thousands of shipbuilders who worked here during WWII.
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Portland Breakwater Lighthouse
5m
Get a photo of Portland Breakwater Light (affectionately called "Bug Light" because of its small size).
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John Ford Statue
Pass by
Get an up close view of this statue dedicated to one of the most distinguished movie directors in history, and learn about his connections to his hometown of Portland.
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Old Port
Pass by
See the center of the bustling downtown/waterfront district known as the Old Port. Learn the history of this vibrant area of Portland that is home to countless eclectic shops, businesses, and world class restaurants and bars.