13 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.

Kids can pretend they are lobstermen, veterinarians, shopkeepers, or actors in a play at Portland's small but fun Children's Museum. Most exhibits, many of which have a Maine theme, are hands-on and best for kids 10 and younger. Have a Ball! teaches about the science of motion, letting kids build ramps that make balls speed up, slow down, and leap across tracks. Don't miss the life-size inflatable humpback whale rising to the ceiling at the whale exhibit. The outdoor pirate-ship play area is a great place for a picnic lunch. Camera Obscura, an exhibit about optics, provides fascinating panoramic views of the city; it's aimed at adults and older children, and admission is therefore separate.

A lovely 55-acre space designed by the Olmsted Brothers, Deering Oaks is frequented for its sparkling pond, playground, and games at its baseball diamond. It’s also the summer home of the Portland Farmer’s Market, and you’ll find its playground and water features enjoyed by kids on any warm day. A well-kept rose garden and wide clusters of native trees are draws for gardeners and botanists.

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.

A laid-back brewery with a focus on IPAs and sour ales, Fore River has plenty of brews to sample and plenty to do while hanging at the fire pit, playing corn hole or dog frisbee (canines are welcome in the yard), or listening to live music. Specialties from various food trucks are here as well; call ahead or visit the website to see what trucks are scheduled. 

Baseball doesn't get much more authentic, close up, or old school than at Hadlock, home to The minor league Portland Sea Dogs. Whether you've come for the excellent sight lines, to watch a specific player (the team is a feeder for The Boston Red Sox, after all), or just to soak up the old school thrill of watching a mascot throw prizes to kids in the crowd, you're in for a few hours of smiles and vintage Americana. 

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.

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.

Developed beginning in 1836 and landscaped by the Olmsted Brothers, this 18-acre park is one Portland's oldest preserved spaces. It offers wonderful sunset views in spots, as well as a network of wooded trails, places to sit and people-watch, and paths that pass by the neighborhood's historic homes.

A good place to start is at the head of the Western Promenade, which has benches and a nice view. From the Old Port, take Danforth Street all the way up to Vaughn Street; take a right on Vaughn and then an immediate left onto Western Promenade. Pass by the Western Cemetery, Portland's second official burial ground, laid out in 1829—inside is the ancestral plot of poet Henry Wadsworth Longfellow—and look for street parking.