In 1623, the first Europeans tried settling on a peninsula sheltered from the Atlantic Ocean by a large waterway filled with islets. Their failed attempt at colonization evolved into Maine’s largest city encircled by Casco Bay. Enjoy the sites, history and charm of Portland, Maine.
Approximately 100 cruise ships annually berth at the Ocean Gateway Pier in Portland, Maine. Is there anything for a day tripper to do or see in Maine’s largest city? Plenty! Explore the picturesque waterfront. Treat yourself to lobster. Hop aboard one of several sightseeing tours. Walk through the Old Port, Arts District and along historic Congress Street. Savor the scenery of Casco Bay as you stroll along the Eastern Promenade. Then visit three of Maine’s spectacular lighthouses. Before you start using this travel guide, verify when you need to be back onboard. You will need all the time you can get to fully enjoy Portland.
14 Ocean Gateway Pier, Portland, ME 04101
From the cruise terminal, begin exploring downtown Portland by walking west on Commercial Street. This main artery runs parallel to the waterfront. Most of this area caters to tourists. Several buildings have stories to tell about Portland’s history if you could only hear them whispering. The Workingmen’s Club is an example. During the Irish Potato Famine (1845 – 1852), immigrants primarily from County Galway arrived in droves. Most found laborious yet welcome work along the docks as longshoremen or for the railroad. Not surprising, they spent their off hours in taverns. From 1851 until 1856, Maine prohibited alcohol. Afterwards, the late-night carousing returned. In response, Bishop O’Connell commissioned the Workingmen’s Club. When the social environment for the Irish opened in 1905, one rule for membership was total abstinence.
21 Commercial St, Portland, ME 04101
Casco Bay separates Portland from the Atlantic Ocean. The large waterway is dotted by a dozen major islands, more than 200 islets and seven lighthouses. Picturesque is just one of many appropriate superlatives. An inexpensive way to enjoy this scenery is aboard a Casco Bay Ferry at the Maine State Pier. This essential transportation of island commuters is your ticket to great coastal sightseeing. This ferry is named Aucocisco, the Abenaki word for the bay. It means “a place of herons.”
56 Commercial St, Portland, ME 04101
An architectural reflection of the former importance of Portland’s seaport is the United States Custom House. The façade is clad in grey granite and features an elegant Second Empire design by architect Alfred B. Mullett. This served as the custom offices from 1872 until 2012. Unfortunately, tours are rarely available to admire the two-story central hall. The space is decorated with marble flooring and counters, walnut woodwork, ornate railings and a coffered ceiling.
312 Fore St, Portland, ME 04101
The Abenaki Native Americans lived here for millenniums before Portuguese explorer Estêvão Gomez’s discovery in 1524. The next European visitor was Englishman Captain John Smith in 1614. The first of several attempts at settlement began in 1623. In 1786, the town of Portland was established. A key to growth was maritime trade because this is the closest U.S. port to Europe. The harbor’s success accelerated in 1820 when the city became the capital of the new state of Maine. A further boom occurred after 1853. That is when a railroad was connected to Montreal. Portland rapidly became the winter port serving Canada when other harbors in Atlantic Canada and the St. Lawrence River were icebound. After the 1920s, shipments at the wharfs declined and the area deteriorated. In the 1980s, a rebirth began along the waterfront and the Old Port neighborhood. That is what you are experiencing today: a blend of the historic and the new all facing Portland’s Harbor. Most of the vessels you will see are cruise ships, sightseeing tours and lobster boats like those shown here.
86 Commercial St, Portland, ME 04101
As their name implies, Portland Discovery Land and Sea Tours offers many options for viewing the city highlights during the tourist season. This trolley is a one-hour ride around downtown Portland. An extended version encompasses nearby lighthouses. You can also select from several harbor cruises. Can’t decide? Then do both; special discount packages are available.
170 Commercial St, Portland, ME 04101
Few sights in nature are more exciting than watching a whale breach the surface, perform a gravity-defying summersault then slap its enormous tail while plunging back into the water. Experience this thrill aboard a four-hour boat ride captained by Odyssey Whale Watch. Chances are superb you will see whales – especially humpbacks, finbacks and minkes – plus pods of dolphins. Whale watching season runs from early May through mid-October.
170 Commercial St, Portland, ME 04101
There are sixteen wharfs along Commercial Street. They begin at Franklin Street (a block west of the cruise terminal) and stretch for about .75 miles to Park Street. These former working docks – Union and Widgery Wharf date back to the late 18th century – have been transformed into a haven for tourists. Huddled together are eateries, pubs, shops, tour operators, historic vessels, a fish market plus wonderful views of Portland Harbor. You could have a wonderful day without ever leaving the waterfront.
1 Long Wharf, Portland, ME 04101
If you are a lobster aficionado, then Portland is the place to don a plastic bib and grab a set of claw crackers. There are over 75 restaurants in the city with lobster on the menu. The settings range from white tablecloths to waterfront shacks on stilts. Ambiance is no predictor of taste. Every bite is butter-dripping delicious. This abundance of lobster is a Maine hallmark. The state’s fishermen catch over 100 million pounds of lobster a year. The peak season runs from late June into December.
180 Commercial St, Portland, ME 04101
North of Commercial Street and south of Federal Street is the Old Port District. Here you will discover boutique stores, diverse restaurants and charming pubs intermingled with small plazas and squares. A good place to start is Moulton Street shown here. Then meander left, right or straight ahead. Each direction reveals more delights. Soon you will notice most of the buildings are brick and appear to be from the Victorian Era. There is a reason for this consistency. On July 4, 1866, the Great Fire of Portland devastated 1,500 buildings and left over 10,000 people homeless. At the time, this was the worst fire in U.S. history. Remarkably, over 600 buildings were constructed in less than six months. You are walking among the rebirth of Portland.
11 Moulton St, Portland, ME 04101
Exchange Street runs north-south through the heart of the Old Port District. Amble slowly along the red brick sidewalks. Window shop to your heart’s content. Pick up something special from one-of-a-kind stores. Stop for a drink or bite to eat. This historic neighborhood is one of the main reasons (pun intended) Portland is a unique destination. When you are ready (there is no hurry), walk west on Middle Street. Within a block it becomes Spring Street.
37 Exchange St, Portland, ME 04101
You have entered the Arts District of Portland. This area contains most of the city’s museums, art galleries and theatres plus numerous quality restaurants and historic buildings. An example is the Charles Q. Clapp House. This rare survivor of the 1866 fire is named after the original owner and architect. Clapp created this stunning Greek Revival home in 1832, probably to broadcast his success in business and real estate development. Shortly before the fire, the property was owned by the city’s mayor. Historians explain this was a temporary city hall and records archive after the government locations were destroyed. The Charles Q. Clapp House is now owned by the Portland Museum of Art.
97 Spring St, Portland, ME 04101
Next door to the Charles Q. Clapp House is an older estate: the McLellan-Sweat Mansion. The Federal Era design by architect John Kimball was finished in 1801. The original owner was Hugh McLellan. He was the leader of Maine’s shipping industry until the early 1800s. In 1816, Charles Clapp lived here. Another notable resident was Lorenzo Sweat. This late 19th century politician was a state senator and U.S. representative for Maine. Since 2002, the McLellan House has been part of the Portland Museum of Art.
107 Spring St, Portland, ME 04101
Portland has suffered two major fires. Each time the city rebuilt and became stronger. The first was at the hands of the British during the American Revolution. The most destructive, city-wide fire occurred in 1866. Isolated fires have also destroyed major landmarks such as the City Hall Fire of 1908. No wonder Portland’s flag and crest features a phoenix with the word Resurgam. This is Latin for “I shall rise again.” Want to learn more about these events and how the Portland Fire Department has served the city since 1786? Then visit the Portland Fire Museum. It is located inside this 1837 firehouse, the former home of Fire Engine 4. Among the displays are vintage firefighting equipment and trucks. Unfortunately, the museum is rarely open. Check ahead for details.
157 Spring St, Portland, ME 04101
After the Great Fire of 1866, many people relocated to the West End. Most built narrow, wooden, two-story homes. They are still standing in this quiet Victorian neighborhood. The area is worth exploring if you have the time. But at least walk to the outer edge of the West End to see the Victoria Mansion. This brownstone estate with an Italianate design was built for Ruggles Sylvester Morse. He was a late-19th century hotel entrepreneur. When you see the opulence inside, you would never imagine this was his summer home. Most of the furnishings are original. The heating, lighting and plumbing were all state of the art for the times. The Morse-Libby Mansion became a museum in 1941. It is definitely worth touring this National Historical Landmark.
109 Danforth St, Portland, ME 04101
The Portland Museum of Art is the showcase of the Arts District. The forerunner of this prized institution began in 1882. In 1908, they were gifted the McLellan-Sweat Mansion on Spring Street. In 1983, PMA opened this main location called the Charles Shipman Payson Building. Today, the collection exceeds 20,000 pieces of art including the works of several famous European painters such as Picasso and Rodin. From this view on High Street, you can see the David Shaw Sculpture Park in the Joan Burns Garden. On the right is Human Structures, a steel sculpture by Jonathan Borofsky.
7 Congress St, Portland, ME 04101
In 2019, the Portland Museum of Art continued their expansion into neighboring landmarks when they purchased the Children’s Museum & Theatre of Maine. Since the theatre was founded in 1923 and the museum in 1976, they have been dedicated to educating, inspiring and entertaining Portland’s youth. There are three floors of interactive displays designed to delight the minds of children. Since 1830, this building has housed a Baptist church and the Portland Chamber of Commerce before the Children’s Museum moved here in 1993.
142 Free St, Portland, ME 04101
There are plenty of taverns, bars and clubs in Portland. They range from high-priced cocktails prepared by mixologists to local watering holes. Perhaps this diversity is a safe haven to help all Mainers endure their winter. Mathew’s on Free Street claims to have opened in 1872, making it the oldest pub in Portland. No one can remember that far back, so their claim is undisputed. Other than longevity, Mathew’s is unremarkable. Think draft beers or shots straight from the bottle starting midday. The décor includes old photos, a pool table, dart game and TVs showing sports. Some might call this a dive while others prefer the description neighborhood bar. Pull up a stool if you want to mingle with the locals.
133 Free St, Portland, ME 04101
If you inherently love the design of flatiron buildings, you will want to admire the H.H. Hay. Its triangular shape has been defined by Free, High and Congress Streets since 1826. The Hay Company was an apothecary from 1841 until 1964. In addition to mixing medicines to order, they dispensed flavored drinks from their soda fountain.
594 Congress St, Portland, ME 04101
Congress Street is the main east-west avenue through downtown Portland. In the late 18th century, this was called Back Street because it defined the edge of town. Wealthy residents selected the area to build their impressive homes. When Portland was the capital of Maine (1820 – 1832), numerous state and municipal buildings were constructed. This attracted the development of hotels, commercial businesses, retailers, museums and churches. Several were spared during the 1866 fire. The addition of new construction – in a wide variety of architectural styles – continued until the Great Depression. In short, Congress Street is a reflection of Portland’s history from about 1785 through the 1930s. This travel guide identifies many highlights along Congress Street from High Street, through the residential neighborhood in the East End and to the shores of Casco Bay.
547 Congress St, Portland, ME 04101
This home was built in 1786 by Peleg Wadsworth, a general in the American Revolution. He and his wife raised eleven children in this brick mansion. Among them was Zilpah Wadsworth. After she married Stephen Longfellow, one of their eight children to live here was the famed 19th century poet Henry Wadsworth Longfellow. After his younger sister’s death in 1901, the Longfellow boyhood home was gifted to the Maine Historical Society. The Wadsworth-Longfellow House is now a fascinating museum. The décor reflects the family’s lifestyle in the late 19th century. It is attached to the Maine Historical Society Museum on Congress Street.
489 Congress St, Portland, ME 04101
There often seems to be one or two buildings in a city that a visitor walks by without a passing glance yet locals consider iconic. This is the case with the Time & Temperature Building. The façade is nice but not extraordinary. The former Chapman Building is not historic – it was built in 1924. Nor is it the tallest – it ranks third at 173 feet. So, what makes it endearing? Above the 14th story is a huge eggcrate screen with incandescent light bulbs. They have displayed the time and temperature almost non-stop since 1964.
477 Congress Street, Portland, ME 04101
When the 11th floor of the Fidelity Trust Company Building was finished in 1910, its height of 135 feet qualified as Portland’s tallest. It also was higher than any structure north of Boston. Especially attractive are the architectural motifs displayed on the Beaux-Arts façade clad in Bedford Indiana limestone. This high-rise has always been home to a bank tenant. But the name keeps changing each time a different institution moves in. The current moniker is People’s United Bank Building.
467 Congress St, Portland, ME 04101
Monument Square is a triangular downtown plaza. Since 1891, the centerpiece has been the Soldiers and Sailors Monument. This is a tribute to the Union servicemen from Portland who died during the American Civil War. Atop the granite base is Our Lady of Victories. The 14 foot sculpture by Franklin Simmons holds a sword and shield while wearing a laurel wreath symbolizing triumph. The bronze figure personifies Minerva, the Roman goddess of war and wisdom. At the base are additional statuary representing the Army and Navy.
456 Congress St, Portland, ME 04101
The name of the First Parish Church is very appropriate, especially when you learn their past. Fishermen were the earliest Europeans to live in this area in 1633. In 1658, the land was claimed by the Massachusetts Bay Colony. They named the village Falmouth. These colonists founded a congregation in 1674, the forerunner of this church. After the settlement was destroyed twice – first by the Abenaki people in 1676 and then by the French in 1690 – the colony was abandoned for over a decade. This parish restarted in 1718. They built three successive churches during the 18th century. The 1740 version, called Old Jerusalem, withstood a bombardment of British cannonballs in 1775. Today’s granite facade was finished in 1826. The Simon Willard clock tower dates back to 1802. Miraculously, the First Parish Church was one of the few surviving structures of the city-wide fire in 1866. In short, the First Parish Church is a mirror of Portland’s history.
425 Congress St, Portland, ME 04101
The attractive Beaux-Arts design of the Portland Masonic Temple helped get the 1911 building named on the National Register of Historic Places. Yet the facade belies the incredible interior. Imagine a Scottish Rite Reading Room encircled by dark hardwood paneling, a fireplace and lit with a chandelier and sconces. Or The Armory surrounded by York Rite Masons’ cubicles, glass windows by Tiffany and a colonial U.S. flag. Most impressive is the two-story ballroom named Corinthian Hall because of the numerous columns. Since 2013, this lodge has been available for special events and is a popular wedding venue.
415 Congress St, Portland, ME 04101
Handsome! That is the short description of the Portland City Hall. This is the third rendition of the municipal headquarters built on this site within fifty years. Two predecessors were destroyed by fire; the first in 1866 and the second in 1908. This version by architect John Carrere is impressive, especially for the size of Portland in 1912. The Beaux-Arts-style building only has four floors. Yet, when measured to the top of the weathervane on the clock tower, its 130 feet qualifies as one of the city’s tallest structures. Officed here are the mayor, city council members, their staffs and various municipal departments.
389 Congress St, Portland, ME 04101
The Cathedral of the Immaculate Conception is the mother church of the Roman Catholic Diocese of Portland. As fate would have it, the cathedral had to be built twice because the fire in 1866 destroyed the nearly-completed first version. This structure was consecrated in 1869. The magnificent spire soars 204 feet. This height qualifies the Cathedral of the Immaculate Conception as the tallest building in Portland and number two in Maine. The Gothic Revival style was created by Patrick C. Keely. The Irish-born architect is credited with designing over 500 churches – predominately along the Eastern Seaboard – during the second half of the 19th century. Guided tours of the cathedral are available on the first Sunday of each month.
307 Congress St, Portland, ME 04101
Encircling the Cathedral of the Immaculate Conception is a block-long complex of buildings consisting of the bishop’s residence, a school and this Cathedral Hall facing Congress Street. Architecturally, the brick facades of these structures share some of the cathedral’s Gothic features yet are less ornate. The former Guild Hall is now home to the St. Vincent de Paul Soup Kitchen.
313 Congress St, Portland, ME 04101
The Saint Paul missionary was established in 1763 when today’s Portland was named Falmouth. Their first church succumbed to a British bombardment in 1775 during the American Revolution. The second structure suffered the same fate as the rest of the city when destroyed by fire in 1866. This third St. Paul’s Anglican Church was finished in 1868. The multi-color stones on the Gothic Revival façade sparkle in the sunshine like facets of a gemstone. The symbols in the stained-glass rose window represent the Four Evangelists: Saints John (eagle), Luke (calf), Mark (lion) and Matthew (man).
279 Congress St, Portland, ME 04101
You have now entered Munjoy Hill. The major landmark in this otherwise residential neighborhood is the Portland Observatory. The tower is only 86 feet tall. However, because it is located near the peak of the hill, the elevation is 222 feet. This height was perfect to observe – using a fixed telescope – incoming ships hours before they reached the port docks. A signalman used flags to communicate with the arriving vessels and then notified workers along the wharfs using additional flags. The octagonal wooden tower was operational from 1807 until 1923. The maritime signal station is now a seasonal museum. The cupola is an observation platform for tourists.
138 Congress St, Portland, ME 04101
The United States celebrates 1776 as their Declaration of Independence. However, Great Britain did not formally recognize the end of the American Revolutionary War until 1783. Afterwards, the new country worried about retaliation. So, a decade later, they began building a network of batteries along the eastern coastline named the First System of Seacoast Defense. One of these fortifications was placed on Munjoy Hill in 1794. It was originally named Fort Allen and later became Fort Sumner. The blockhouse and cannons are long gone. But Sumner Park is still worth visiting. The elevated position provides a wonderful view of the city skyline, especially at sunset. You can also admire the circular Back Cove. The estuary is especially attractive during the autumn when foliage is ablaze.
59 North Street, Portland, ME 04101
Portland is located on a rectangular peninsula with the East End protruding into Casco Bay. Hugging the shoreline is a 78 acre park. This is a favored recreational area for locals. Among the amenities are ball fields, a public tennis court, a community garden, a playground and a boat launch. Dogwalkers along the Midslope Trail are easily distracted by the scenery. On the left is the Marine Yacht Center in the neighborhood of East Deering.
Eastern Promenade Midslope Trail, Portland, ME 04101
Almost anywhere you stand along a Portland shoreline you will see some of the Casco Bay Islands. There are over 200 of them. Seen here from the Eastern Promenade are Mackworth Island (center) and Great Diamond Island (right). Six of the major islands are served by ferry. For a real scenic treat, consider the Mailboat Run aboard the Maquoit II. While this working vessel is delivering packages and cargo, you will enjoy the archipelago of Casco Bay for 2.5 to three hours. The tour is provided by Casco Bay Lines located at the Maine State Pier near the cruise terminal.
First Civic Monument, Cutter St, Portland, ME 04101
Portland is almost surrounded by water. Yet the East End Beach is the only stretch of sand. This is the perfect place to spend a summer day with your family. The waters of Casco Bay are typically calm and ideal for swimming. Kayak and paddleboard rentals are nearby. So are restrooms. Bring a meal to eat on a picnic table. Let the kids burn off energy at the playground. Offseason is equally ideal. Then you can cherish this picturesque scenery in solitude.
East End Beach, Eastern Promenade Trail, Portland, ME 04101
Encircling the East End shoreline of Casco Bay is the Eastern Promenade. The well-groomed trail stretches for 2.1 miles at the base of Munjoy Hill. This is a favored place for runners, cyclers, walkers and couples out for a romantic stroll. At the elbow of the headland is Fort Allen Park. This nine acre high ground was chosen in 1775 to install a battery to defend the city. Today, it displays old artillery from the USS Portland (a cruiser used in WWII) and the USS Maine (its sinking in Cuba prompted the Spanish-American War). The views of the bay from the 1890 bandstand are outstanding.
Fish Point, Eastern Promenade Trail, Portland, ME 04101
From the 1870s through the 1940s, a network of trains chugged along 200 miles of two-foot-wide track while serving remote communities in the state. The system has been dismantled but not forgotten. Since 1992, the Maine Narrow Gauge Railroad Company has operated a train museum in the former Portland Company Marine Complex. This was a nine acre rail yard established in 1846. They also offer scenic rides in vintage passenger cars. The route parallel to the Eastern Promenade is short – three miles round trip – but loads of fun. All aboard!
49 Thames St, Portland, ME 04101
Your walking tour of central Portland is concluded. You are now back at the Ocean Gateway Passenger Terminal. From here you can get back onto your cruise ship to have a meal, cocktail and maybe a nap before it sails. Or, if you have extra time and love lighthouses, then grab a cab and show the driver the next five photos.
14 Ocean Gateway Pier, Portland, ME 04101
About a 15 minute drive from downtown Portland’s waterfront is Bug Light Park, located in the city of South Portland. The main attraction of this nine acre park is the Portland Breakwater Light. Locals call the squat, 26 foot high lighthouse the Bug Light. The cone-shaped, cast-iron exterior resembles Greek architecture with six Corinthian columns. This beacon has marked a breakwater at the entry to the Portland Harbor since 1875. The design was created by Thomas U. Walter. This famous architect created the Senate and House Wings plus the central dome at the U.S. Capitol in Washington, D.C. The masted sailing ship is the Bagheera, first launched in 1924. The windjammer is a sightseeing tour of Casco Bay operated by the Portland Schooner Company.
Bug Light Park, S Portland Greenbelt Pathway, South Portland, ME 04106
During World War II, 140 acres in South Portland was a shipyard dedicated to manufacturing vessels. 236 Liberty Ships – a class of cargo ship – were built here during a four year period. In 1996, about nine acres of the old shipyard were converted into Bug Light Park. To acknowledge the contribution made to the war effort by about 30,000 people, the Liberty Ship Memorial was erected in 2001. The steel silhouette designed by Richard Renner measures 65 feet long and 35 feet tall.
Bug Light Park, S Portland Greenbelt Pathway, South Portland, ME 04106
The War of 1812 and the American Civil War prompted the need to defend the mouth of Portland Harbor. Fort Gorges was finished in 1864. It never saw military action. The namesake for the fortress was Sir Ferdinando Gorges. He was a 17th century military commander of Plymouth, England. Gorges helped establish the Province of Maine in 1622. This earned him the title “Father of English colonization in North America.” Fort Gorges is located in Casco Bay on Hog Island Ledge. Hog Islander is a slang term for WWII troop and transport ships like those previously built in today’s Bug Light Park where this photo was taken. You can tour the island but it is only accessible by water.
Fort Gorges, Hog Island Ledge, South Portland, ME 04101
The Spring Point Ledge Lighthouse is a popular spot to visit near Portland. The conical, cast-iron light stands 54 feet at the end of a 900 foot breakwater. The formal name for the design is caisson. The colloquial term is a sparkplug lighthouse. It was built in 1897 at Fort Preble. The woman is comfortably reading in one of the embrasures of the old, star-shaped fort. The fortress was constructed in 1808 when tensions were rising with Britain prior to the War of 1812. During peak armament, there were 14 heavy guns aimed toward Casco Bay. Fort Preble was deactivated in 1950. The property is now part of the Southern Maine Community College.
Lighthouse Circle, South Portland, ME 04106
There are over 150 lighthouses along 6,000 miles of New England’s coast. Ship’s navigation technology has made most of them obsolete. However, they are still busy as beacons to tourists with cameras. Maine has 66 lights. The oldest is Portland Head Light in Williams Park. The 80 foot lighthouse is located in a suburb of Portland called Cape Elizabeth. George Washington commissioned the light in 1787. It began shining four years later. The keeper’s house dates from 1891.
12 Captain Strout Cir, Cape Elizabeth, ME 04107