Things to Do in Portland, Maine: Casco Bay's Working City

The Munjoy Hill Cluster: Observatory, Eastern Promenade, and East End Beach

Munjoy Hill, Portland's easternmost peninsula neighborhood, is the closest thing the city has to a single walkable recreation district. At its top stands the Portland Observatory, built in 1807 as a maritime signal tower — used to spot incoming ships and signal their owners in the harbor before modern communication existed. Multiple preservation sources describe it as the only remaining historic maritime signal station of its kind still standing in the United States, and it carries National Historic Landmark status.

Wrapping around the hill is the Eastern Promenade, a 68.2-acre waterfront park whose construction began in 1836 and continued periodically through 1934, designed by the Olmsted Brothers firm (founded by the sons of Frederick Law Olmsted, designer of Central Park), with landscape architect Charles R. Goodell overseeing a regeneration of the promenade in 1878. Today it includes a 2.1-mile paved multi-use trail popular with cyclists and runners, sports fields, and Fort Allen Park, a 9.33-acre section holding remnants of a Revolutionary War and War of 1812-era fort, a 1929 granite bench honoring Civil War Union Army service, a memorial to 21 American prisoners of war who died aboard the British prison ship HMS Regulus in 1812, and the mast of the USS Portland, a heavy cruiser commissioned in 1933 that fought in all four major 1942 Pacific carrier battles.

At the base of the promenade sits East End Beach, Portland's only public swimming beach — a small sand-and-pebble beach with a boat launch, panoramic views of Casco Bay's islands, sailboats entering and leaving the harbor, and, at times, seals visible on offshore rocks. Portland is a real waterfront city with almost no traditional ocean-swimming-beach frontage of its own, unlike some of its neighboring towns, which is exactly what makes this one beach precious to residents rather than a drive-to-a-neighboring-town errand.

The Old Port and Commercial Street: Shopping District and Working Waterfront at Once

The Old Port is Portland's historic waterfront district — cobblestone streets and 19th-century brick warehouse buildings, with Middle and Exchange Streets as its main commercial spines. It was formally listed on the National Register of Historic Places as the "Portland Waterfront Historic District" on May 2, 1974, and its warehouses were converted into restaurants, shops, and residences starting in the 1970s. Today it mixes boutiques, restaurants, and bars with the city's still-active cruise-ship terminal and working piers.

Commercial Street, created by 1850s landfill and running the length of the waterfront, is the literal seam that ties it together: a 2008 American Planning Association profile and a feature in Maine Boats, Homes & Harbors magazine both describe the street as blurring the distinctions among working waterfront, downtown main street, and historic tourist district, with marine and non-marine uses coexisting rather than competing. Portland's harbor itself is described as Maine's largest and most diverse, anchored by roughly 15 central piers and wharves — including Union Wharf, Widgery Wharf, Merrill's Wharf, and Custom House Wharf — supporting lobsterboats, groundfishing for cod and haddock, a deep-water cruise-ship pier that opened in 2011, and a container-cargo terminal operated by the Icelandic shipping company Eimskip.

Portland Museum of Art

The Portland Museum of Art was founded in 1882. Its downtown campus grew around the McLellan House, a Federal-style mansion completed in 1801 and bequeathed to the museum in 1908 along with funds for the L.D.M. Sweat Memorial Galleries, a Beaux-Arts building designed by architect John Calvin Stevens that opened in 1911. The museum's own site cites a collection of more than 19,000 artworks, including works by Winslow Homer, Andy Warhol, Louise Nevelson, and Claude Monet.

One distinction worth keeping straight: the museum acquired Winslow Homer's actual studio in 2006, and guided studio tours depart from and return to the PMA's downtown building at 7 Congress Square — but the studio itself sits at Prouts Neck, which is physically in the town of Scarborough, not Portland. The museum building and its downtown collection are genuinely Portland's own; the studio and its art-colony history belong to Prouts Neck and Scarborough.

Casco Bay Lines: Day-Trip Ferries from Portland's Own Terminal

Casco Bay Lines traces its roots to 1878, when the Casco Bay Steamboat Company began permanent year-round service; the modern nonprofit operator, the Casco Bay Island Transit District, was created by Maine state legislation in 1981. Its terminal sits on Portland's own waterfront (a major renovation doubled the building's size and opened in 2014), and it serves seven Casco Bay islands. Even short of a full island itinerary, a same-day round trip is a genuine, currently bookable Portland activity: the ferry to Peaks Island alone takes about 17 minutes each way, with more than a dozen daily departures.

A Nationally Recognized Restaurant and Brewery Scene

Portland's food scene is a real, independently documented draw in its own right, not just a backdrop to sightseeing. Bon Appétit magazine named Portland its "Restaurant City of the Year" for 2018, a national honor independently covered by The Seattle Times, Boston Magazine, Boston.com, WJLA, and Maine Public. Chefs Mike Wiley and Andrew Taylor, co-owners of Eventide Oyster Co., The Honey Paw, and Hugo's, won the James Beard Award for Best Chef: Northeast in 2017.

Portland also carries a strong brewery reputation: a 2019 C+R Research study found Portland had 18 breweries per 50,000 people, ranking it first among more than 500 U.S. cities assessed at the time — a real but now several-years-old figure. More recently (data updated through December 2024), Vinepair and Statista rank Maine as the #2 U.S. state for breweries per capita, at 14.16 breweries per 100,000 residents statewide, behind only Vermont. Either way, eating and drinking your way through Portland is a genuine "thing to do" here, not filler between stops.