Guide to the Historic Landmarks of Portland, Maine

With this blog, we are traveling to the beautiful city of Portland, Maine! Known for its rich history, picturesque landscapes, and charming coastal views, Portland offers a plethora of historic landmarks that are sure to captivate visitors. 

In this guide, we will explore various historic landmarks in or near Portland. If anything we write in this guide inspires you to visit Portland with Summer Feet, please check out our Portland Bicycle Day Trips and our multi-day Maine Bicycle Trips.

Portland Head Light

Portland Head Light in Cape Elizabeth

Located in Cape Elizabeth, just a short drive (or cycle) from downtown Portland, the Portland Head Light is one of the most recognized and beloved lighthouses in the United States.

This historic landmark has been guiding ships into the entrance of Portland Harbor since 1791, making it Maine’s oldest lighthouse. History lovers can dig into the rich history surrounding the lighthouse, and everyone can enjoy the elegant beauty of this local treasure.

The picturesque beauty of Portland Head Light has attracted countless photographers, artists, and tourists throughout the years. Standing tall, at 80 feet, the lighthouse is perched atop a rugged cliff, overlooking the crashing waves of the Atlantic Ocean. 

The surrounding Fort Williams Park offers visitors a chance to stroll along scenic trails, have picnics, and explore the remnants of an old military fort. If you’d like to visit Portland Head Light by bicycle, check out our 6-day Portland History and Harbors Bicycle Tour

For a shorter trip, our 5 Lighthouse Bike Tour in Portland visits five lighthouses in one day, including Portland Head Light. 

Drink From a Benson Bubbler

This isn’t one landmark, but 52 tiny little landmarks… You may notice quaint little bronze drinking fountains throughout Portland. These fountains add to the city’s aesthetic, but there is also an equally quaint origin story behind them…

In 1912, there was a well-respected local businessman called Simon Benson who was particularly well known for his dislike for alcohol. When he smelled alcohol on the breath of men who worked for him, he asked why they felt the need to drink alcohol during the day.

The men responded that there was no access to fresh water in downtown Portland. Benson — always a man of action — immediately gave $10,000 to Portland City to buy 20 bronze drinking fountains, fitting them at convenient places. Here’s the great part (for Benson, at least): beer consumption dropped by 25%!

Keep an eye out for one of these fountains, which the locals affectionately refer to as Benson Bubblers. In fact, you can still drink from the original Benson bubbler, which you can find right on the corner of Washington Street and Southwest Fifth Avenue.

Victoria Mansion

Victoria Mansion, an impeccably preserved Italianate villa

Credit – Dennis Jarvis

Step into the elegance and opulence of the Victorian era at the Victoria Mansion. This impeccably preserved Italianate villa, built between 1858 and 1860, and also known as the Morse-Libby House or Morse-Libby Mansion.

Victoria Mansion showcases exquisite craftsmanship, lavish interiors, and stunning period furnishings. Take a guided tour to learn about the history and architectural significance of this historic Landmark.

You can find out more about it on the official Victoria Mansion website, which includes special events and activities that are time sensitive. So, make sure to check out the website before your visit.

Portland’s Old Port

The heart of Portland, the Old Port, is a historic district filled with cobblestone streets, brick buildings, and a lively atmosphere. While more of an area than a distinct landmark, there is so much to see of historic significance in the Old Port.

Stroll along the waterfront and indulge in the eclectic mix of boutiques, art galleries, cafes, and restaurants. Immerse yourself in the city’s maritime past and perhaps even look around for a local tour guide to show you the ropes. 

For many, it’s the Old Port’s nightlife that is the biggest draw — with cocktail bars and pubs in relatively high concentration. If you want to do a bit of a bar crawl, you’ll want to visit the Old Port.

Wadsworth-Longfellow House

Wadsworth-Longfellow House


This beautifully preserved house was built in 1785 and it offers a glimpse into the life and works of the beloved Portland poet famous for his historical epics based on contextual American history and myths, such as: The Song of Hiawatha, Evangeline: A Tale of Acadie, and Paul Revere’s Ride.

Take a guided tour of Wadsworth-Longfellow House museum; here, you’ll tour the house while also seeing Longfellow’s personal belongings, and gain insight into his literary contributions. This is the perfect option for any fans of Henry Wadsworth-Longfellow’s work.

Maine Historical Society

For a comprehensive exploration of Maine’s history, make your way to the Maine Historical Society. Located in the heart of Portland’s downtown, this institution is dedicated to preserving and sharing the state’s heritage. 

Browse through their vast collection of artifacts, documents, and photographs that offer a glimpse into the lives of Mainers from centuries past. Don’t miss their museum exhibits, which provide a fascinating narrative of Maine’s rich history.

Portland, Maine, is a treasure trove of history and natural beauty. Whether you’re drawn to the majestic lighthouses, the Victorian elegance of the Victoria Mansion, or the vibrant charm of the Old Port, the city offers something for everyone. 

Of course, there are many more worthwhile landmarks in Portland, but we hope we’ve inspired a few readers to visit. 

If you’d like to explore Portland’s landmarks on one of Summer Feet’s tours, we look forward to welcoming you to our beautiful corner of Maine, and we encourage you to get in touch if you have any questions whatsoever.

Looking for more information about traveling in Portland, Maine? Read our Where to Eat in Portland, Maine next.

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