Self-Guided Driving & Walking Bundle of Portland Maine Tours

Portland’s Harbor (the body of water that you just sailed in on) is a “deep water” port, it generally does not freeze over during the winters. the Gulf of Maine has very strong tides, and those tides mix the water column and bring deeper, warmer water to the surface all along the coast.

Note: This 10+mile-long tour covers the essentials of Portland in 2-3 hours.

Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months.

This is the Victoria Mansion. Built by Ruggles Morse in 1858. “the best standing example of Victorian art, architecture and decoration.” He named it “Victoria Mansion” after Britain’s Queen Victoria, It was built as his summer home.

On the left-hand side, see the colorful brick rowhouses. These were built originally for the servant class, these rowhouses are now very nice… expensive condominiums.

After all those fires, brick was used from that point on throughout the city, not a lot of wood.

The Maine Medical Center is home of the Barbara Bush Children’s Wing. Mrs. Bush, the wife of our 41st president and the mother of the 43rd president, she lived much of her life in Kennebunkport, Maine, 30 miles south of Portland. She passed away in 2018. Mrs. Bush did so much great work raising money for treatment of kids with terrible illnesses, and her legacy is remembered in the Children’s wing of the Maine Medical Center.

On the right side of the coach we’ll pass the home of Neal Dow. A former Portland mayor, Neal Dow is known as the father of the American Prohibition. In 1851, then Mayor Dow pushed through a statewide prohibition-- banning the sale and consumption of intoxicating beverages--that became the model for the National Prohibition.

This is the “Portland’s Arts District”. The area has many independent art galleries, working studios, Coffee houses and restaurants.

Up ahead, on the right, is the Portland Art Museum.

Just past the non-descript building on the right—the gray/brown Maine Historical Society headquarters—is the Wadsworth Longfellow House. It’s the brick building set a little back from the road, on the left. This is the house where the poet grew up. Built after the Revolutionary War by Peleg Wadsworth, a Revolutionary War General and the grandfather of Henry Longfellow, it’s the oldest brick house in Portland.

On our left side is the 1st Parish Unitarian Universalist Church. This is the oldest church in Portland. The building is the second building that has housed this congregation.

On the left is Portland’s City Hall, a beautiful building for a small city. This is the third City Hall building on this site. The first two building were destroyed by fire

The tall brick and concrete building to your left is the Franklin Tower, built in the 1970s. It’s the tallest building in the state of Maine at 16 stories.

Here’s Portland’s Eastern Cemetery, it’s the oldest cemetery in the City of Portland

Some Head Stones date back to1768. The oldest markers were wooden, and they were lost to the fires.

Let’s go back to the 1800’s, during that time, ships entering Portland Harbor could not be seen from the docks until they rounded the point of land at Spring Point Ledge and were almost in the harbor.

Notice that there are several examples of the “flattop triple-decker” this tenement housing style, which is very typical here in New England, were built in the 1880s to the 1920s.

Off to the right is Portland Harbor. Part of Casco Bay, an inlet on the Southern Coast of the Gulf of Maine, the City of Portland sits along its southern edge and the Port of Portland lies within.

If you look over your right shoulder, see the land mass with the oil tanks. That's the City of South Portland.

The Eastern Promenade is a great space where Portlanders get out and enjoy the nice weather

and the sea breezes, at the foot of the Eastern Prom is a little beach called the East End Beach.

After the British destroyed city in 1775, Portland’s city leaders decided that they need to build a fort. The green space on the right is the result of that decision.

You'll remember earlier we spoke about the streets in Old Portland, how they were named due to their proximity to the water. They are Fore St, Middle St and Back St.

Continuing our drive here in Portland, we will make our way to the Casco Bay Bridge. The Bridge spans Casco Bay and connects the City of Portland with the City of South Portland.

While we make our way through the City of South Portland we approach Meetinghouse Hill. Meetinghouse Hill is a kind of quintessential New England scene with the cemetery on the left and the Civil War statue on the right and a beautiful church behind the Civil War statue.

We’re now entering Fort Williams Park. You’ll notice several military installations here in the park

Explore the charm, history, and vibrant culture of Portland, Maine, with this self-guided walking tour! Immerse yourself in the sights and sounds of Portland as you traverse the historical cobblestone streets of Old Port.

Note: This 3+mile-long tour covers the essentials of Portland Walking in 1-2 hours.

It was the labor of love of Ruggles Sylvester Morse, a wealthy New Orleans-based hotel owner. He hired a top architect to turn this into his summer home in 1860.

Dedicated to the American poet Henry Wadsworth Longfellow.

It’s one of the oldest art institutions in the country, founded in 1882. While the museum grew significantly over the years, space, storage, and administrative problems plagued it.

Longfellow lived and wrote some of his most famous works here, including his first poem at thirteen.

That statue in the center of the square is Our Lady of Victories, inspired by the Greek goddess of wisdom and war, Minerva.

The present Renaissance Revival structure was completed in 1912. But it replaces another city hall which succumbed to fire in 1908.

Portland’s Lincoln Park rose from the ashes of the Great Fire of 1866. We’ve seen many testaments to Portlanders’ resilience.