Best ways to see Portland: Staff Picks

With temperatures warming, Spring is the perfect time to find new ways to see the city.

Casco Bay Lines

The ferry service is the easiest way to see Portland from the water and to explore the city’s island communities. Online editor Emily Davis recommends the mailboat cruise, which carries passengers, mail, and freight to Little Diamond, Great Diamond, Long, Cliff, and Chebeague Islands. “Bring a sandwich and a coffee onboard,” she says. “It’s a great way to show visitors the islands quickly.”

From Casco Bay Bridge

For a different perspective, Maine magazine managing editor Kelly Chase recommends crossing the bridge from South Portland in the morning, just as the first light of the day is illuminating Portland. As the bridge bends to the left, Portland’s waterfront comes into view.

Driving End-to-End

Although there’s plenty to see on foot, driving allows you to visit the overlooks on the two ends of the peninsula without taking up too much of your day. Start with either the Western Promenade or the Eastern Promenade, but be sure to see both—and end with a picnic lunch overlooking the water.

Maine Narrow Gauge Railroad

Ride this historic two-foot-gauge railroad for both the history lessons and views of Casco Bay. The Maine Narrow Gauge Railroad Company and Museum, which features exhibits about Maine’s narrow gauge railway history and a train ride along the Eastern Promenade, is open from May through October.

Waterfront on Wheels

There are plenty of jetties reaching out into the harbor from Commercial Street to explore, suggests Mali Welch, art director at the Brand Company. “My mom and I used to rollerblade (yes, rollerblade) all along the waterfront wharfs, anywhere that didn’t have a barrier,” says Mali Welch, art director at the Brand Company. “Lots to discover.”

Portland Trails

The nonprofit organization has built and maintained a network of 70 miles of public trails and green spaces in greater Portland. Its trails include in-town paths like Back Cove Trail and getaways like the treks through the Fore River Sanctuary.

Top of the East 

Many consider the sweeping view from the Top of the East the best in Portland, and it’s hard to argue—especially with a cold martini in hand. The building that was long the Eastland Park Hotel is now called the Westin Portland Harborview, but the view of the city—and name of the bar—have remained the same.

View from the Tower

The Portland Observatory on Munjoy Hill is open for tours starting in May and offers 365-degree views of the entire peninsula and beyond. Originally used as a maritime tower, the landmark offers a vantage point for seeing the Casco Bay islands.

Duck Boat Tour

The amphibious sightseeing ride from Downeast Duck Adventures covers some
of Portland’s best-known landmarks—from the Wadsworth-Longfellow House to Casco Bay’s Fort Gorges— while sharing stories about Portland’s history.

Vintage Shop Loop

For a tour of some of Portland’s vintage shops—from carefully curated boutiques to stores overflowing with antiques— start in the West End and head east on Congress Street before cutting over to Free Street and ending in the Old Port. After the walking tour of vintage wares, find a restaurant to grab a drink and afternoon snack.



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