Portland’s Forgotten Heart
Walking our original downtown: the eastern waterfront
By Colin Woodard
Portland’s eastern waterfront is undergoing a profound transformation right before our eyes. The industrial, working-class neighborhood of the recent past is rapidly giving way to hotels, condominiums, office buildings, parking garages, and cruise ship infrastructure. Big projects are expected to rise at the Maine State Pier, the old Jordan’s Meats plant, the Village Café, and Shipyard Brewing Company’s site. Several others are already completed or in progress nearby.
The India Street area is well on its way to becoming Exchange Street East, but without the sense of rooted-ness and authenticity afforded by the Old Port’s Victorian streetscapes. Most of the development here is being built from scratch in a part of town whose rich past has been largely destroyed by war, fire, economic catastrophe, and wrongheaded urban “renewal” projects. New construction reflects this historical amnesia, producing a new “neighborhood” not unlike any other gentrified, urban tourist district in the country.
That’s a pity, because the eastern waterfront is arguably the most historic neighborhood in Portland.
The first colonists settled here in 1632, a stone’s throw from the foot of the Ocean Gateway terminal nearing completion next to the Maine State Pier. Throughout the colonial period, this part of town was Portland, the center of its commerce, government, cultural affairs, industry, and population. It’s the site of our city’s first house, farms, ferry, pub, church, courthouse, customs house, and cemetery. George Burroughs — the alleged leader of the witches hanged during the Salem Witch Trials — preached to the town faithful on one side of what’s to become the $100 million Riverwalk project; Henry Wadsworth Longfellow was born on the other side.
India Street — King Street before the Revolution — was the town’s main drag for much of the 17th and 18th centuries, a period during which the settlement was wiped out three times. Indians attacked and destroyed it in 1676. A decade later, settlers returned, only to be slaughtered by a French and Indian assault in 1690. It was resettled again in 1718, and by the 1770s, the community had become one of British America’s wealthiest outposts thanks to the trade in forest products, including masts for the Royal Navy.
The neighborhood’s prominence came to a sudden end in 1775, when a British naval force bombarded the city, unleashing a fire that destroyed the area and condemned many residents to death from hunger and exposure. After the Revolutionary War, Portland’s center shifted west to Exchange Street, but the eastern waterfront remained a desirable residential area into the mid-19th century, when the city fathers filled in the coves to build rail terminals, train yards, and foundries, creating the industrial legacy still visible today.
While several mega-projects proposed for the eastern waterfront remain delayed by financial or political complications, this is an opportune time to get acquainted with the area’s history — a wellspring of inspiration that has remained sadly untapped.
Having taken this walking tour of Portland’s forgotten heart, perhaps a developer will be moved to name a hotel lounge after old Widow Greele, or city officials could decide to display photos of the Grand Trunk train terminal inside the Ocean Gateway marine terminal. But if we dare to dream, we’ll see a new urban neighborhood that’s as walkable, welcoming, bustling and beautiful as the lost ones it’s replaced.
We’ll start at the base of Ocean Gateway [1; click numbers to view map]. Due to ongoing construction, you can’t actually walk here, but no matter. When Portland’s first settler, George Cleeve, arrived on this spot in 1632, he couldn’t set foot on it either. To do so, he’d have had to walk on water.
Until the mid-1800s, waves lapped along what is now Fore Street, and this area was a sheltered harbor called Broad Cove. If you stand on Fore Street just above the Hamilton Marine complex  and look east, you can see the ghost of the Broad Cove shoreline gently arcing along the inside of Fore Street up to the bluff where the Portland Company stands.
Cleeve came ashore on the beach just a few paces east of the once-and-future corner of Fore and Hancock streets . (The byways intersected until the 1950s, and will soon be reconnected when the city extends Hancock Street southward.) Here he built Portland’s first house amid a thick forest. The fields of his farm extended west along the shore nearly to present-day India Street, and included land being dug up to build an office building and parking garage at the corner of Fore and India. Cleeve’s woodlots reached back as far as the Village Café parking lot, where a condo complex may soon rise. A brook ran down the hill nearby, providing water for his livestock, and the shore’s gentle slope gave him great beach access.
Until Broad Cove was filled in during the 1840s, this was prime waterfront property. In the early 1700s, the finest homes in town were located along this stretch. Henry Wadsworth Longfellow was born in one of them, a 1798 house which, despite later becoming a museum, was razed in 1955 to make way for the expansion of a small industrial concern.
Portland’s first church , a one-story meetinghouse, stood on the bluff that marked the eastern end of Broad Cove, where the Portland Company’s driveway meets Fore Street. The Rev. Burroughs preached here until the outbreak of King Phillip’s War, when he moved to Salem and met his untimely demise.
The Maine State Pier , the Hilton Garden Inn, and the base of Franklin Arterial occupy what was once Clay Cove, the center of the colonial waterfront. Clay and Broad coves were separated by a stubby point that jutted out from the corner of Fore and India streets. Fort Loyal , the town’s primary fortification, was built in 1678 on a bluff at the end of this point.
(In a rare nod to historicity, the new eastern extension of Commercial Street has been named for Thames Street, a short byway on the point Fort Loyal stood upon that was later incorporated into Commercial Street.)
Fort Loyal was constructed when settlers returned to the area after the end of King Phillip’s War. It served as a provisional town hall and fortification of last resort when hostilities resumed in May of 1690. That’s when between 400 and 500 French and Indian troops attacked Portland. The settlers, grossly outnumbered, held out for four days before surrendering, at which point 200 were murdered. According to 19th century historian Nathan Goold, the “dead bodies lay exposed to the wild beasts and birds and the bleaching storms for two years,” just a few paces from the front door of Benkay Japanese Restaurant. When the third Indian war broke out in 1716, authorities decided to evacuate Portland and demolish the fort, rather than risk another bloody catastrophe.
Throughout the colonial period, India Street was Portland’s principal thoroughfare, the spine connecting Fore, Middle and Back (now Congress) streets to one another and, via the docks and the Country Road (a dirt track running through the wilderness along the present-day route of outer Congress Street), to the rest of the world.
In 1690, Silvanus Davis, the commander of Fort Loyal, maintained the region’s only store , which was licensed “to retail liquors out of doors.” The building stood at the head of the town landing on Broad Cove, where Davis also operated the first Casco Bay ferry (1686). It carried people and horses over to Nonesuch Point in South Portland, where a path proceeded to Cape Elizabeth.
Portland’s first pub  opened in September of 1681 just a few yards to the east of Davis’ store, on Fore Street. Proprietor Richard Seacomb received his first fine eight months later, for serving Indians.
In the early- and mid-1700s, the center of town was the corner of present-day Middle and India streets . The first custom house, built in 1766, stood at this intersection (where Jordan’s Meats is expected to make way for a hotel and condo development). The courthouse (1774) stood in the Port City Glass parking lot on the west corner; on the north corner was the second Puritan meeting house (1721-28), a wooden clapboard building where, in August 1727, British and Wabanaki representatives ratified the peace treaty ending King George’s War.
All of these buildings were destroyed in 1775, when Lt. Henry Mowatt of HMS Canceaux, an eight-gun British warship, burned much of Portland to the ground in retribution for having been kidnapped by Brunswick revolutionaries while strolling along Back Cove a few months prior. The October 18th bombardment lasted nearly nine hours, setting a fire that left three-quarters of Portland in ruins. In the aftermath, armed yahoos from Gorham poured into town to loot the remains. The destruction of India Street and the old waterfront was so complete that the area never really recovered.
The fire claimed the home of the Rev. Thomas Smith , an imposing Congress Street mansion built in 1728 opposite the head of India Street. It was one of the finest houses in town, and the first to have wallpaper. Rev. Smith entertained lavishly with the assistance of his slaves, hired scalp hunters to keep the Indians in check, and made a small fortune in real estate speculation. His sermons were remembered for their long-windedness.
One important building that wasn’t destroyed in the fire of 1775 was Alice Greele’s Tavern , erected circa 1735 in what’s now the Congress Plaza parking lot at the corner of Hampshire and Congress streets. For decades, this was the most popular gathering place in the city, “a fashionable resort for old and young wags,” in the words of 19th century historian, attorney, and Portland Mayor William Willis. “It was the Eastcheap of Portland,” Willis wrote, in reference to Shakespearean London’s nightlife district, “and was as famous for baked beans as the Boar’s Head was for sack.”
When the Canceaux’s red-hot shot set fire to her backyard, Widow Greele stood her ground, fighting the flames and proclaiming to a passerby: “They will have to stop firing soon, for they have got out of bombs and are making new ones [so quickly they] can’t wait for them to cool!” She saved the tavern, and the county court met there until they got around to building a new courthouse 12 years later. The structure was moved to Washington Avenue in 1846, where it burned in the Great Fire of 1866. Near the base of the strip mall’s sign, a large wooden plaque commemorates this lost landmark.
The one place in the area where you can find physical remains from the colonial era is the Old Burying Ground , established in the late 17th century in what now comprises the southwestern quarter of the Eastern Cemetery on Congress Street. (The gates are usually locked, but you can get the key at Carlson & Turner Books across the street.) Early settlers — including Cleeve — were buried around an enormous Norway pine that once stood on the ridge and served as a landmark for mariners trying to make the town landing below. A smaller pine and a plaque mark the spot these days, though the early tombstones offer no clues as to who lies underneath. The earliest marked stones start in 1717, and include many of the people for whom Portland’s streets are named, as well as the commanders of the uss Enterprise and the hms Boxer, killed fighting each other off Monhegan during the War of 1812.
Below the cemetery, at 73-75 Newbury Street, is the former Abyssinian Church , a wooden structure built in 1828 that dodged destruction in the 1866 fire. It is the oldest African-American church still standing in the country, and was part of the underground railroad that provided sanctuary for runaway slaves prior to the Civil War. The boarded-up structure is listed in the National Register of Historic Places, and a non-profit group has been working for the past decade to raise money to restore it.
Heading back down the hill, you may want to avoid the urban travesty that is Franklin Arterial . Completed in the early 1970s, the byway devastated the blue-collar neighborhood in its path and severed the East End from the rest of the city. (In 1967, a skeptical city councilor equated the Franklin plan to the erection of the Berlin Wall.) If you do head this way, try not to get run over — 1960s-era highway engineers cared about cars, not pedestrians — and take notice of the footpaths East Enders have had to tramp down themselves in lieu of non-existent sidewalks. (A recently completed peninsula traffic study calls for expanding Franklin Arterial to nine lanes in order to facilitate traffic going to and from Ocean Gateway and the Maine State Pier — a disaster that would rank alongside the destruction of Union Station for sheer stupidity.)
At the base of Franklin, take a left back to India Street. You’re walking on mid-19th-century landfill that made it possible for trains to travel the length of the harbor, on what is now Commercial Street, to the Grand Trunk Station , a stately brick structure built in 1903 and demolished in 1966 to make way for a parking lot. Only a small section survives, the part that housed the steamship offices.
The Maine State Pier and Ocean Gateway projects straddle the old steamship wharves, which provided passenger connections to Boston, Rockland, and Liverpool, England. Nineteenth-century development was notably inter-modal — passengers could walk right from the steamship to the railroad station, or hop a streetcar to other points in the city. The new projects proposed for the pier envision enormous parking facilities.
From here you can again see the Portland Company complex . Constructed in 1846, it was originally a railroad foundry that built the locomotives, rolling stock, and the railroad ties that connected us to Montreal. In so doing, this connection made Portland a major shipping port practically overnight. Over 600 locomotives and 160 ships were built at the 160,000-square-foot complex, including two Civil War–era gunboats. The Maine Narrow Gauge Railroad runs from switching yards and tracks that once belonged to the Grand Trunk — another all too rare allusion to the eastern waterfront’s past.
Colin Woodard is an award-winning journalist and the author of The Lobster Coast and The Republic of Pirates. He lives in Portland. colinwoodard.com.