6 Best Sights in East End, Munjoy Hill, and Washington Ave., Portland

Portland's only public beach, it's set at the bottom of the hill of the Eastern Promenade. Its panoramic views of Casco Bay make it a popular summer spot, as do amenities like convenient parking, picnic tables, and a boat launch. Amenities: food and drink; parking (fee); toilets; water sports. Best for: sunrise; sunsets; swimming; walking.

To experience the city's busy shoreline and take in the grand views of Casco Bay, walkers, runners, and cyclists head out on the 2.1-mile Eastern Prom Trail.

Beginning at the intersection of Commercial and India Streets, this paved trail runs along the water at the bottom of the Eastern Promenade, following an old railbed alongside the still-used railroad tracks of the Maine Narrow Gauge Railroad Co. & Museum. There are plenty of places with benches and tables for a picnic break along the way. From the trailhead, it's about 1 mile to the small East End Beach.

Continuing along the trail, you’ll pass underneath busy Interstate 295, and emerge at the Back Cove Trail, a popular 3½-mile loop you can connect with for a long trek. To return to the Old Port, backtrack along the trail or head up the steep path to the top of the promenade. Here you can continue along the promenade sidewalk or take the trails through this 68-acre stretch of parkland to the lovely picnic area and playground.

Continuing along the sidewalk toward the Old Port, a gazebo and several old cannons to your left indicate you’re at the small Fort Allen Park. Use one of the coin-operated viewing scopes to view Civil War–era Fort Gorges, which never saw action.

Where the Eastern Prom becomes Fore Street, continue on for a few blocks to India Street and take a left, which will bring you back to where you started. Or, continue into the Old Port.

Plan at least an hour to walk the trail with brief stops, or two if you continue along the Back Cove Trail. But if you can, make time for the Prom—it’s truly an urban jewel.

Between the city's two promenades, this one, often overlooked by tourists, has by far the best view. Gracious Victorian homes, many now converted to condos and apartments, border one side of the street. On the other is 68 acres of hillside parkland that includes Ft. Allen Park and, at the base of the hill, the Eastern Prom Trail and tiny East End Beach and boat launch. On a sunny day the Eastern Prom is a lovely spot for picnicking, snacking (there are always a few top-notch food trucks), and people-watching.

Whether you're crazy about old trains or just want to see the sights from a different perspective, the railroad museum has an extensive collection of locomotives and rail coaches, and offers scenic tours on narrow-gauge railcars. The 3-mile jaunts run on the hour, at 10, 11, noon, 1, 2, and 3 every day in the operating season. Rides take you along Casco Bay, at the foot of the Eastern Promenade. The operating season caps off with a fall harvest ride (complete with cider), and during the Christmas season there are special Polar Express rides, based on the popular children's book.

This octagonal observatory on Munjoy Hill was built in 1807 by Captain Lemuel Moody, a retired sea captain, as a maritime signal tower. Moody used a telescope to identify incoming ships, and flags to signal to merchants where to unload their cargo. Held in place by 122 tons of ballast, it's the last remaining historic maritime signal station in the country. The guided tour leads all the way to the dome, where you can step out on the deck and take in views of Portland, the islands, and inland toward the White Mountains.

When owner (and self-titled “boochmaster”) Reid Emmerich looked around Portland and realized that lots of locals were drinking kombucha but none of it was being made locally, he set his sights on fixing that in 2018. These days the funky tasting room-cum-brewery (it’s technically licensed as the latter, since all kombucha contains at least a small amount of alcohol) gets filled with fans in to try Emmerich’s latest flavors—which change with whatever ingredients are in season, since he forages many of them himself—and hang out with fellow boochlovers in the process.