Historic Downtown Portland

When we visit a new city, I like to book a walking tour through the local historical society. Walking tours are a great way to learn more about the local culture, get a feel for the street layout, and support a local institution.

On Thursday I took a walking tour of historic downtown Portland. Our guide, a Portland native named Dugan, had a gift for teaching history through engaging and funny stories. His approach was to point out a building, tell an anecdote without naming the historical figure, and then reveal that person’s identity (if we hadn’t managed to guess it already). A couple of times, the mystery figure turned out to be Dugan!

Portland was home to the indigenous Wabanaki people and was settled by the British in 1632. It has always been a resilient city, rebuilding itself after being destroyed by fire four times (Dugan described the great fires as “three wars and an accident.”) Its culture has been shaped by many different waves of immigrants; first from Ireland, Italy, and Germany; then from Lebanon, Syria, and Greece; and later from Vietnam, Eritrea and Somalia. Along with being a commercial seaport, Portland has, through the years, been a major manufacturer of steam locomotives and a major producer of canned sardines and canned corn. Now, it’s a destination for tourists who love microbreweries, award-winning restaurants, and boats.

We walked through all the main areas of downtown Portland: the Government District, the Arts District, the Old Port, and the Waterfront. Dugan kept us well-entertained, even as the morning sky turned ominously dark and the street lamps automatically came on. And sure enough, halfway through our walking tour, it started to rain. A true Mainer, Dugan barely paused, simply opening up the big umbrella that had been slung across his back, and continuing with his stories.

After the tour, I stopped by a donut shop to see what all the fuss was about. They were tasty enough, but I’m not a big fan of donuts.

City Hall

City Hall weather vane, gleaming despite the gray skies!

City seal with non-native dolphins and mythical phoenix

Civil War-era cannonball proudly displayed

First Parish Church (now Universalist Unitarian)

Original weathervane from 1740 church

Legend has it that during the Revolutionary War, a young man fired a musket at the weathervane and spun it around. No one believed him. But centuries later, the steeple was renovated, and the original weathervane was found to have a dent, just the size of a musketball!

Monument Square

Near site of the country's first gymnasium

Monument Square

Wharf Street in Old Port district

Dark skies at 11:00am!

One of Portland's wharfs in the rain

Taking shelter from the rain

Which flavor would you choose?

I chose blueberry lemon, maple bacon, and dark chocolate sea salt (Steve and Amy helped me eat them)

On Friday, after our visit to Allagash Brewing Company, I took Steve and Amy on an abbreviated walking tour of the Old Port District. It was nice to wander through those charming cobblestone streets without any rain.

John Ford Statue

A native of Portland, Ford directed over 140 films, including Stagecoach, The Searchers, The Grapes of Wrath, and The Quiet Man

Wharf Street, without rain!

Wharf Street

U.S. Custom House

Buskers on the waterfront

Boat moored at Long Wharf

Portland Lobster Co. at sunset - where we would return the next day!

Fun fact: Portland, Oregon was named after Portland, Maine, thanks to a coin toss in 1845 between business partners Asa Lovejoy (of Boston, Massachusetts) and Francis Pettygrove (of Portland, Maine).