History of Portland, Maine

Perched on a scenic peninsula that juts into Casco Bay, Portland, Maine is a city where centuries of history meet a thriving cultural and culinary scene. Its story is one of resilience, reinvention, and maritime tradition.

Early Settlement and Colonial Beginnings

The region now known as Portland was originally inhabited by the Abenaki people, who fished, hunted, and traded along the coast for thousands of years. In 1623, English explorer Christopher Levett established a settlement in the area, which was soon followed by a larger colonial presence.

By 1633, settlers had founded a fishing and trading village called Casco, later renamed Falmouth. This early outpost endured numerous conflicts, including repeated attacks during King Philip’s War and King William’s War in the late 1600s. By the early 1700s, the area had been destroyed and rebuilt multiple times.

A City Reborn

In 1786, Falmouth Neck was renamed Portland, honoring the English Isle of Portland. Thanks to its deep harbor and advantageous location, the city flourished as a maritime and commercial hub—shipping timber, fish, and goods across the Atlantic.

Portland was nearly destroyed during the Great Fire of 1866, which burned more than 1,800 buildings just four days after the Fourth of July. But the city rebuilt quickly, and many of the stately brick buildings seen today in the Old Port date from this post-fire period.

In the 19th century, Portland also became a key center of rail and ocean transportation. The city was the eastern terminus of the Grand Trunk Railway to Montreal and a winter port when Canadian harbors were frozen. Prominent residents like Henry Wadsworth Longfellow, one of America’s most famous poets, brought cultural prestige to the city.

20th Century to Today

As shipping declined, Portland reinvented itself again. The Old Port transformed from a gritty dockyard into a vibrant mix of shops, galleries, and restaurants. The city became a haven for creatives, chefs, and entrepreneurs, emerging as one of New England’s most dynamic small cities.

Today, Portland is celebrated for its working waterfront, preserved architecture, innovative food scene, and access to Maine’s rugged coastal beauty. It strikes a unique balance between historic charm and modern vibrancy.

Top 25 Attractions in Portland, Maine

1. Old Port District
Cobblestone streets, 19th-century brick buildings, boutique shops, restaurants, and a working harbor define this charming downtown area.

2. Portland Head Light
One of America’s most iconic lighthouses, built in 1791, set within Fort Williams Park in nearby Cape Elizabeth.

3. Eastern Promenade
A scenic waterfront park with walking trails, panoramic views of Casco Bay, picnic areas, and access to East End Beach.

4. Portland Museum of Art
Home to works by Winslow Homer, Andrew Wyeth, and Monet, this museum anchors the city’s cultural scene.

5. Victoria Mansion (Morse-Libby House)
A stunning 19th-century Italianate mansion filled with original furnishings and elaborate interiors.

6. Casco Bay Lines Ferry Terminal
Hop on a ferry to explore the islands of Casco Bay—including Peaks, Chebeague, and Great Diamond Islands.

7. Fort Gorges
Accessible by kayak or boat, this Civil War-era granite fort stands guard in the middle of Casco Bay.

8. Wadsworth-Longfellow House
Childhood home of poet Henry Wadsworth Longfellow and one of the oldest brick buildings on the Portland peninsula.

9. Portland Observatory
Built in 1807, this maritime signal tower is the only remaining one of its kind in the U.S., offering sweeping views from the top.

10. Maine Narrow Gauge Railroad Co. & Museum
Enjoy a ride along the waterfront on restored trains and learn about Maine’s unique narrow-gauge railway history.

11. The Children’s Museum & Theatre of Maine
Hands-on exhibits and performances that delight kids and families, now housed in a beautiful new facility near Thompson’s Point.

12. Thompson’s Point
An industrial-chic destination featuring breweries, food trucks, concerts, art spaces, and skating in winter.

13. Peaks Island
A short ferry ride from downtown takes you to this laid-back island with beaches, bike rentals, and historic sites.

14. Allagash Brewing Company
Take a tour or sample award-winning Belgian-style beers at one of Portland’s pioneering craft breweries.

15. International Cryptozoology Museum
A quirky and fascinating museum exploring the study of unknown or legendary animals like Bigfoot and lake monsters.

16. Maine Historical Society
Located next to the Wadsworth-Longfellow House, this center offers rotating exhibits and rich archives on Maine’s past.

17. Deering Oaks Park
A large public park with duck ponds, tennis courts, walking paths, a seasonal farmers market, and plenty of green space.

18. Western Promenade
A less-traveled gem offering western-facing sunset views, historic homes, and peaceful walking paths.

19. Portland Symphony Orchestra at Merrill Auditorium
Enjoy live classical and pops performances in a beautiful historic concert hall.

20. Holy Donut
A beloved local institution offering Maine potato donuts in unique flavors like maple bacon and sea salt chocolate.

21. Tandem Coffee & Bakery
Housed in a former gas station, this hip spot blends house-roasted coffee with top-tier baked goods.

22. Portland Stage Company
Catch a play at Maine’s leading professional theater company, offering a full season of thought-provoking productions.

23. Bissell Brothers Brewing
One of Portland’s most popular breweries, known for juicy IPAs and a lively industrial taproom.

24. Bug Light Park
In nearby South Portland, this coastal park features the tiny “Bug Light” lighthouse, a walking path, and excellent views of the Portland skyline.

25. Baxter Boulevard and Back Cove Trail
A 3.5-mile loop around a tidal basin with serene views, popular with walkers, joggers, and bikers.

Portland, Maine, is a coastal city that has weathered wars, fires, and economic change—only to emerge stronger, more artistic, and more inviting with each new chapter. Whether you’re admiring its historic lighthouses, indulging in its award-winning food scene, or strolling along its scenic bayside trails, Portland rewards visitors with a rich blend of past and present. From cobblestone charm to island escapes, it’s no wonder Portland continues to capture the imagination of travelers from near and far.