6 Best Sights in Portland, Maine

One of the city's most relaxing outdoor spaces, Back Cove Trail is a 3.6-mile paved loop with gorgeous views of the Cove, harbor, and downtown. It's a favorite route for walking, running, biking, and dog walking. Several benches and seasonal water fountains can be found along the trail.

Most visitors stumble on this stunning performance venue thanks to its national and international musical acts—and indeed, it's an ideal size and structure for that with a 3,000- to 8,000-person capacity; it's spacious but not too big to enjoy the show. But that's just the beginning of what the peninsular, waterfront spot offers, from ice skating in the winter to local craft fairs throughout the year. And on select Thursdays and Fridays from 4 pm till sunset in the summer, entry is free, dogs are welcome, and live music and lawn games are on offer with some of the city's best food trucks lining up to feed the happy crowd.

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.

Local ingredients take the spotlight at this family-owned brewery, with sprawling indoor and patio spaces and even bigger list of seasonal creations (like blueberry sour ales and Marzen-style lagers) and year-round beers like Ishmael, a malty and sweet ale. There's also wine and kombuchas on offer.