Portland Maine Introduction Walking Tour, Portland

Portland Maine Introduction Walking Tour (Self Guided), Portland

If New York is the city that never sleeps, then Portland, Maine is the city that always dreams. Its magic is in its quiet, gentle allure. Located on the southern edge of Casco Bay, along the U.S. Atlantic coastline, Portland is known, among other things, for its picturesque natural setting.

Albeit the largest and most populous city in the State of Maine, there is a certain 'small-town' charm that wraps around you like a cozy, worn-out blanket in Portland – a feeling you may never want to shake off.

Before Europeans, the area was initially inhabited by the indigenous Algonquian people, who called it Machigonne, which means "great neck". English explorer Christopher Levett founded the first English settlement on the land in 1623. However, it was abandoned and the area became part of Massachusetts Bay Colony, in the 1650s.

Throughout the late 17th and early 18th centuries, a new town, named Falmouth, was destroyed and rebuilt several times. In 1786, it was officially renamed Portland. Curiously, the name 'Portland' was decided after a coin toss between the two British settlers. The victor, a former resident of the Isle of Portland in Dorset, England, chose to name it after his home place, while the other contender wanted to call it Boston after his native town in Lincolnshire, England – oh, well...

In the 19th century, Portland became one of the most important seaports in New England. The historic Old Port district with its picturesque cobblestone Wharf Street and the running along the waterfront Commercial Street, lined with historical buildings, today offers a glimpse into the city's maritime past.

A large part of the city was destroyed in the Great Fire of 1866, but then was quickly rebuilt and continued to grow. During the 20th century, amid a decline in its shipping industry, the city emerged as "a beacon of culture and creativity in the northeastern U.S." and a major culinary destination recognized nationwide.

If you want a taste of Maine, look no further than Portland, they say. “From its seafood to its people, it's as authentic as it gets.”

Strolling through the streets of Portland, you can't help noticing a perfect blend of past and present, where history breathes through the cracks of modernity. To experience it first-hand and not get lost along the way, take this self-guided walk.
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Portland Maine Introduction Walking Tour Map

Guide Name: Portland Maine Introduction Walking Tour
Guide Location: USA » Portland (See other walking tours in Portland)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 8
Tour Duration: 2 Hour(s)
Travel Distance: 2.5 Km or 1.6 Miles
Author: nataly
Sight(s) Featured in This Guide:
  • Monument Square
  • Congress Street
  • Exchange Street
  • Old Port and Wharf Street
  • DiMillo Marina
  • Commercial Street
  • Victoria Mansion
  • Portland Museum of Art
Monument Square

1) Monument Square

Monument Square is a central plaza situated in downtown Portland. It is positioned between the East Bayside and Old Port neighborhoods. Notable buildings such as the Time and Temperature Building, Fidelity Trust Building, and the main branch of the Portland Public Library can be found on Congress Street, facing the square. Additionally, several other structures, including One Monument Square and One City Center, are located within the square.

At the heart of Monument Square stands the Portland Soldiers and Sailors Monument, situated on the former site of Portland's City Hall. Unveiled on October 28, 1891, this monument pays tribute to the courageous soldiers and sailors of the United States Army and Navy who lost their lives defending the country during the Civil War. Often referred to as "Our Lady of Victories," the monument features a bronze statue mounted on a granite base. The statue depicts a female figure symbolizing Victory, dressed in armor and flowing robes. She holds a furled flag in one hand and a mace and shield in the other. Bronze groups of three figures, representing soldiers and sailors, stand on two sides of the base.

Maine sculptor Franklin Simmons created the sculpture, while New York City architect Richard Morris Hunt designed the base. The original landscaping of the site, which has since been significantly modified, was the work of Portland architect Francis H. Fassett. Local fundraising efforts organized by the Grand Army of the Republic lodge made the creation of the monument possible. On April 1, 1998, it was added to the National Register of Historic Places.
Congress Street

2) Congress Street

Congress Street, the primary thoroughfare in Portland, extends from the city's southwestern border with Westbrook, passing through various neighborhoods, until it reaches the Eastern Promenade on Munjoy Hill. Recognizing its historical significance, the Portland City Council designated a significant portion of the inner section of Congress Street as an official historic district in March 2009. Notably, the western part of the street is home to the city's vibrant Arts District.

When British colonists established what is now Portland in the early 18th century, the population primarily settled near the waterfront, specifically around present-day India Street. Congress Street, initially known as Back Street and later renamed Queen Street, was carefully planned. The street's early prominent structures included the First Parish Meeting House, constructed in 1740 and replaced with the current building in the 1820s, as well as the hay scales in Market Square, which would later be referred to as Monument Square. During the period leading up to the American Revolutionary War, Back Street marked the town's outskirts. In 1823, it was officially renamed Congress Street.

In 1921, the Etz Chaim Synagogue was built towards the eastern end of Congress Street, near Munjoy Hill. Remarkably, as of 2011, it remained the only immigrant-era synagogue in Maine that still operated.
Exchange Street

3) Exchange Street

Exchange Street, situated in the charming Old Port of Portland, is a bustling commercial thoroughfare. It serves as a home to various high-end fashion boutiques alongside several locally owned enterprises. Additionally, you can find a couple of delightful coffee shops, including one that also functions as an Internet café. In 2015, the opening of Exchange Street Studio brought an independent ballet school and dance studio to the area.

Historically, Exchange Street served as a prominent location for numerous printing presses and newspapers. Positioned strategically at the intersection of Congress Street and opposite Portland City Hall, the Press Herald Building was constructed in 1923. It underwent an expansion in 1948 to become the headquarters of the Portland Press Herald. Following a renovation in 2015, the building was transformed into the elegant Press Hotel.

Exchange Street is renowned as the primary center of activity in the Old Port. However, in the years leading up to the 1970s, both Exchange Street and the surrounding Old Port district had fallen into disrepair and abandonment. The process of gentrification took root in the early 1970s and has continued transforming the area ever since.
Old Port and Wharf Street

4) Old Port and Wharf Street (must see)

The Old Port, also known as the Old Port Exchange, is a captivating district located in Portland. Its charm lies in its cobblestone streets, 19th-century brick buildings, and fishing piers, which evoke a sense of history and character. As you stroll or drive down these cobblestone streets, you're immediately transported to a different era, where each stone tells a story, adding to the allure of the experience.

The Old Port district is a vibrant hub filled with an array of boutiques, restaurants, and bars, making it a popular destination for tourists and locals alike. The district's reputation for vibrant nightlife adds to its allure, drawing visitors from far and wide. However, it's not just the establishments that attract people to the area but also the ambiance created by the cobblestone streets.

Wharf Street, in particular, has a gravitational pull that captivates its visitors. The exceptional restaurants and tourist sites along this street owe a debt of gratitude to the cobblestone paving. The flickering candlelight illuminating the outside tables of these establishments would not have the same romantic effect without the presence of cobblestone.

In addition to its cobblestone streets and historic buildings, the Old Port includes several adjacent parks. Post Office Park and Tommy's Park provide green spaces for relaxation, while Bell Buoy Park, located next to the Casco Bay Ferry Terminal, offers a picturesque setting. The Eastern Promenade Trail, which terminates in the Old Port, serves as a connection to the East End Beach, allowing visitors to enjoy the beauty of the waterfront.

Today, the Old Port and Wharf Street remain a testament to Portland's rich history and vibrant present. The combination of cobblestone streets, historic architecture, and a thriving culinary and entertainment scene creates a unique and captivating atmosphere that continues to enchant visitors and residents alike.
DiMillo Marina

5) DiMillo Marina

DiMillo Marina, located in Portland, is a renowned destination for boating enthusiasts and visitors seeking a memorable waterfront experience. Situated in the heart of Portland's vibrant Old Port district, this marina offers a unique combination of convenience, luxury, and scenic beauty.

One of the standout features of DiMillo Marina is its prime location on the historic waterfront of Portland Harbor. Nestled on the eastern edge of the city, it offers breathtaking views of Casco Bay, dotted with picturesque islands and framed by the stunning Maine coastline. The marina's proximity to downtown Portland makes it easily accessible and an ideal starting point for exploring the city's numerous attractions.

DiMillo Marina is known for its state-of-the-art facilities and exceptional services, catering to the needs of boaters of all types and sizes. The marina can accommodate vessels ranging from small boats to large yachts, with 125 slips available for transient and seasonal docking. Each slip is equipped with modern amenities, including electricity, water hookups, and Wi-Fi access, ensuring a comfortable stay for boaters.

The marina's renowned full-service boatyard provides a wide range of maintenance and repair services, including engine work, hull repairs, painting, and electronics installation. Experienced technicians are on hand to assist with any boating-related needs, ensuring that vessels are kept in excellent condition.

In addition to its exceptional facilities, DiMillo Marina is surrounded by a wealth of attractions and activities. The marina's central location means that visitors have easy access to the vibrant energy of Portland's downtown area. They can explore the city's unique shops, galleries, and restaurants, or take a stroll along the historic cobblestone streets of the Old Port.
Commercial Street

6) Commercial Street

Commercial Street is a vibrant and historically significant street nestled in downtown Portland. With its rich history and scenic waterfront location, it has become a popular destination for locals and tourists alike. In 2008, it was honored as one of the ten best streets in the United States by the American Planning Association.

The street's origins can be traced back to the 1850s when it was constructed on reclaimed land, made possible by filling Casco Bay. This expansion was necessary to accommodate the growing demands of the railroad and warehousing industries, both integral to the bustling port's working waterfront. The transformation of old piers into a thriving street allowed for improved access and trade opportunities, fueling the city's economic growth.

One notable landmark situated at the intersection of Commercial Street and Franklin Street is the Maine State Pier. Serving as a deepwater marine facility and an outdoor music venue, it adds an exciting dimension to the street's dynamic atmosphere.

At the eastern end of Commercial Street, visitors can discover the historic Widgery Wharf and Union Wharf. These two structures, completed in the late 18th century, stand as testaments to the city's early maritime heritage.

Today, Commercial Street continues to thrive as a bustling thoroughfare, combining the nostalgic charm of its maritime history with the vibrancy of a modern urban destination. It offers a delightful mix of attractions, culinary delights, and unique shopping experiences. Whether strolling along the street, indulging in fresh seafood, or enjoying the cultural events at the Maine State Pier, Commercial Street captivates visitors with its distinct character and rich heritage.
Victoria Mansion

7) Victoria Mansion (must see)

Victoria Mansion, also known as the Morse-Libby House or Morse-Libby Mansion, stands as a remarkable representation of American residential architecture situated in the heart of downtown Portland. This elegant brownstone Italianate villa, completed in 1860, was originally intended as a summer retreat for Ruggles Sylvester Morse, a prominent hotelier who had ventured beyond Maine to amass his fortune in the hotel industry in New York, Boston, and New Orleans.

The house was designed by the esteemed architect Henry Austin, boasting a distinctively asymmetrical structure characterized by a four-story tower, overhanging eaves, inviting verandas, and ornate windows. Adding to its allure, the interior of the mansion showcases intricate frescoes and captivating three-dimensional wall decorations, masterfully crafted by the talented artist and decorator Giuseppe Guidicini.

After serving as a cherished family residence, the mansion witnessed a change in ownership when the last of the Libby family members departed in 1928. Unfortunately, the subsequent economic downturn of the Great Depression, coupled with the devastating 1938 Portland flood, led to the repossession of the house in 1939 due to unpaid taxes. The fate of the abandoned mansion hung in the balance, with plans even surfacing for its demolition to make way for a gas station, proposed by an oil company.

However, the property was saved by William H. Holmes, who recognized the historical significance of the building. Determined to protect its architectural grandeur, Holmes purchased the house in 1941 and lovingly transformed it into the Victoria Mansion, paying homage to Britain's esteemed Queen Victoria.

Victoria Mansion was added to the National Historic Register. Today, it continues to thrive as a captivating museum, inviting visitors to immerse themselves in the opulent splendor of nineteenth-century America.
Portland Museum of Art

8) Portland Museum of Art (must see)

The Portland Museum of Art (PMA) stands as a testament to the rich artistic heritage of the state and the United States as a whole. Established in 1882 as the Portland Society of Art, it is the largest and oldest public art institution in Maine.

In its early years, the museum utilized various exhibition spaces until a pivotal moment in 1908. Margaret Jane Mussey Sweat, a prominent figure in Portland's cultural scene, bequeathed her elegant three-story mansion, now known as the McLellan House, along with sufficient funds to establish a gallery in memory of her late husband, Lorenzo De Medici Sweat, a former U.S. Representative. The L. D. M. Sweat Memorial Galleries were designed by the renowned New England architect John Calvin Stevens and opened their doors to the public in 1911.

With over 22,000 artworks spanning from the 18th century to the present day, the PMA's collection showcases the diverse talents of renowned artists. The museum holds an impressive array of works by celebrated figures such as Winslow Homer, Marsden Hartley, John Marin, Louise Nevelson, Andrew Wyeth, and John Greenleaf Cloudman. Visitors can immerse themselves in the artistic journeys of these talented individuals as they explore the PMA's galleries.

The Portland Museum of Art boasts the most extensive European collection in the state of Maine. Within its halls, visitors can traverse the major European art movements from impressionism to surrealism through the remarkable Joan Whitney Payson, Albert Otten, and Scott M. Black collections. These collections comprise significant works by esteemed artists like Giambattista Pittoni, Mary Cassatt, Edgar Degas, René Magritte, Claude Monet, Edvard Munch, Pablo Picasso, and Auguste Rodin. The Elizabeth B. Noyce Collection comprises 66 paintings and sculptures, including works by George Bellows, Alfred Thompson Bricher, Abraham Walkowitz, and Jamie Wyeth.

Beyond its impressive collection, the Portland Museum of Art also hosts a range of engaging exhibitions and educational programs. These initiatives strive to foster a deeper appreciation for art, encourage dialogue, and inspire creativity among visitors of all ages. The museum's commitment to accessibility and inclusivity ensures that art remains a vibrant and integral part of the community.

Walking Tours in Portland, Maine

Create Your Own Walk in Portland

Create Your Own Walk in Portland

Creating your own self-guided walk in Portland is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
Historical Buildings Walking Tour

Historical Buildings Walking Tour

There is no doubt that Mainers have made a great mark in the history of the United States, and the seaside city of Portland is no exception. The local architectural heritage encapsulates several centuries, reflecting various periods of American history – from the early colonial settlers' homes to the industrious Victorians and their ornate dwellings, all the way through to the modern day...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.1 Km or 1.9 Miles