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Things to do in Old Port, Portland

Our most recommended things to do in Old Port, Portland

Portland: Self-Guided Sightseeing Driving Audio Tour

1. Portland: Self-Guided Sightseeing Driving Audio Tour

Travel through the neighborhoods of Portland on a self-guided driving tour. Learn about the city’s history and culture from an audio-guided app on your smartphone and get panoramic views from the Eastern Promenade.  Start by downloading the app, which will function as your personal tour guide, audio tour, and map all in one. Once downloaded, your Portland tour begins at the Visit Portland Center. Drive down Commercial Street and hear about the industrial beginnings of the city. Along the way, you’ll see the wonderfully preserved Victoria Mansion, dating back to 1858. That’s followed by the even older Danforth Inn, which goes all the way back to 1823. As you drive up the Western Promenade, you’ll hear about some famous folks who were laid to rest in Portland, including the poet Henry Wadsworth Longfellow (a statue of whom you’ll see next, in Longfellow Square). Go to the Art District (perfect for picking up a souvenir), followed by a church that was once destroyed by the British.  Continue toward the shore, passing the site of an observatory that once guided ships into Portland’s occasionally treacherous harbor. Spot a couple of picturesque lighthouses perfect for any photo collection. Explore the Eastern Promenade, a 68-acre seaside park sporting plenty of unforgettable ocean views. You’ll see the strange and controversial “baked beans” building, before passing through Old Port again for a second chance to stop at one of the neighborhood’s many restaurants and boutiques. Pass by a statue of Portland’s own John Ford. Cross the Casco Bay Bridge into South Portland, home to a quieter community than its buzzing northern neighbor. Finally, you’ll arrive at Fort Williams Park, full of beauty and history. The tour concludes here.

Portland, Maine: Local Brewery & Spirits Bus Tour

2. Portland, Maine: Local Brewery & Spirits Bus Tour

Satisfy your taste buds with a variety of brewery bus tour options of different breweries throughout greater Portland, Maine. Generous portions of alcohol products made at each different location are included, along with local snacks and an optional lunch. Beerunch Brewery Tour (3 Hours) Visit the famous Bissell Brothers Brewing before they open their doors to public, then travel to East Bayside to Belleflower Brewing for another exclusive visit before they open their doors to the public. The last stop is at Goodfire Brewing before being dropped off in downtown Portland, Maine. Drinks About Town: Brewery and Spirits Tour (3 Hours) This afternoon bus tour explores different craft alcohol products made in the city of Portland. Start at Shipyard Brewing Company for beer, then Après for hard seltzers and alcoholic ciders, and last Three of Strong Spirits for craft, high-quality rum. All tours end with drop-off at Old Port Spirits and Cigars, a perfect place to pick something up to indulge in later in the night after exploring lively downtown Portland.

Portland: Old Port Seafood Lovers Tour

3. Portland: Old Port Seafood Lovers Tour

Explore Portland’s vibrant working waterfront to view lobster boats often unloading their catch, learn about the historic wharves and their relationship to the sea. Visit a mix of Old Port and waterfront district destinations, and sometimes a locale or two on the fringes, for a progressive lunch. Servings vary from dine-in and to go from restaurants, pubs, markets, and artisanal shops. Learn about the life of lobsters dwelling on the ocean floor and hear about how hardy lobstermen and women haul in their catch year-round, rain, snow, and shine.

Portland, Maine: Black History Guided Walking Tour

4. Portland, Maine: Black History Guided Walking Tour

Wind through the brick sidewalks and cobblestone streets of Portland's Old Port and working waterfront on this guided walking tour. Immerse yourself in the rich story of the Black community in the East End neighborhood. Meet your local guide at the First Parish Church, Portland's oldest church, and begin your journey back in time. Discover the monuments, places of business, and civic institutions where Black Yankees drove the economy and organized for political power. Head to the East End neighborhood to see the homes of Black sailors and stevedores that served as stations on the underground railroad. Admire the churches where Black families worshipped, celebrated, and learned together from the 19-century up to the present day. Learn how Maine's earliest colonial settlements could not have survived without Black insight, skill, and labor. Uncover the story behind the enslaved Black maid who abolished slavery in Maine during the Revolutionary War. Discover the exceptional figures who shaped Portland and the State of Maine over 400 years of Black history. Printed images of the past together with gifted storytelling will bring the past to life. Hear the stories that usually get left out of history tours. A portion of every ticket sale will help fund the restoration of the Abyssinian Meeting House, Maine's oldest and America's third-oldest standing Black church. End your tour at Eastern Cemetery, one-half mile from where it began.

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What people are saying about Old Port, Portland

Overall rating

4.7 / 5

based on 22 reviews

Dugan was absolutely wonderful!! He had thoroughly researched the history of Portland, and the role of African-Americansinits development. His talks were engaging and enthusiastic, and our entire group really enjoyed our experience with him. He was not afraid of the hard truth, and we were impressed with his scholarly approach to his material, with some fun updates included. I highly recommend this tour, and hope to return to Maine soon so that I can take his other tours as well.

Wonderful tour. I made my vacation trip to the city worthwhile. It was informative, inspiring and not too difficult for these old legs to handle! Tohe tur guide was smart, humourous and able to answer any questions that were raised. I would definitely recommend it for anyone going to the area.

Great guide, lots of fun, great beers. What more could one want? We totally enjoyed this tour!

Really enjoyed learning about Portland. Easy to use. The directions were easy to follow.

Jeff and Jim were fantastic tour guides! Rick& I enjoyed them!