Portland Maine Lobster Rolls Lighthouses and Casco Bay

Why visit Portland

Portland has rebuilt itself several times. The city was burned during the colonial wars and the American Revolution, and on July 4, 1866, a fire swept through much of downtown.

Today Portland is best known for its food. For a city of its size it has a remarkable number of well-regarded restaurants, bakeries, oyster bars and breweries, many supplied by local fishermen and farms.

Portland is also a gateway to the Maine coast. Within a short drive you can stand beneath Portland Head Light, walk out to a lighthouse on a granite breakwater, or ride a ferry to the islands of Casco Bay.

The Old Port and downtown

The heart of Portland slopes from Congress Street down to the wharves, packing shops, restaurants, museums and historic homes into a few walkable blocks.

The Old Port

The Old Port is Portland's historic waterfront district, a grid of brick buildings and cobblestone and brick-paved streets such as Exchange, Fore and Wharf Streets. Independent boutiques, galleries, bookshops, bars and restaurants fill the old warehouses and merchant buildings.

Portland Museum of Art and the Arts District

Founded in 1882, the Portland Museum of Art is Maine's oldest and largest public art museum. Its collection is especially strong in American art, including many works by Winslow Homer, who painted at nearby Prouts Neck, along with European and contemporary pieces.

Victoria Mansion

Built between 1858 and 1860 as a summer home for a wealthy hotelier, Victoria Mansion, also known as the Morse-Libby House, is one of the finest surviving examples of Italianate villa architecture in the country.

Wadsworth-Longfellow House

On Congress Street, the Wadsworth-Longfellow House was the childhood home of poet Henry Wadsworth Longfellow and is the oldest standing building on the Portland peninsula. Run by the Maine Historical Society, it is furnished with original family belongings and has a quiet garden behind it.

Munjoy Hill and the Eastern Promenade

At the eastern end of the peninsula, Munjoy Hill is a residential neighborhood of wooden houses, cafes and some of the best water views in the city.

Portland Observatory

Built in 1807 by Captain Lemuel Moody, the Portland Observatory is a red, eight-sided wooden tower that served as a maritime signal station. From the top, Moody used a telescope to spot incoming ships and raised flags to alert merchants waiting in town.

Eastern Promenade

The Eastern Promenade is a large, hilly park that curves around the end of Munjoy Hill above Casco Bay, with lawns, picnic spots and a long paved trail along the water. Below, East End Beach is the only sandy beach on the peninsula, popular for swimming dogs and launching kayaks.

Lighthouses and the islands

Some of the most rewarding sights lie just across the Fore River in South Portland and Cape Elizabeth, or out in Casco Bay.

Portland Head Light and Fort Williams Park

Portland Head Light, in Cape Elizabeth about fifteen minutes' drive from downtown, was first lit in January 1791 and is one of the oldest lighthouses in the country. Its white tower and red-roofed keeper's house above crashing surf are the classic image of the Maine coast.

Bug Light and Spring Point Ledge Light

In South Portland, two smaller lighthouses make a pleasant pairing. Portland Breakwater Light, nicknamed Bug Light for its small size, was built in 1875 with columns inspired by an ancient Greek monument, and it stands in a park with harbor views and a memorial to the Liberty ships built here during World War II.

Spring Point Ledge Light also offers an unusual view straight back across the harbor to the Portland skyline and is a fine place to watch ships passing in and out of the port.

Casco Bay islands

Casco Bay Lines ferries leave from the terminal on Commercial Street for several inhabited islands. The quickest and most popular trip is to Peaks Island, where you can rent a bike or golf cart and circle the island on a perimeter road past rocky shores and summer cottages.

Food and local flavors

The lobster roll is the dish most visitors come for. In Maine it is typically served cold, with chunks of lobster meat lightly dressed in mayonnaise in a toasted, buttered split-top bun, though you can also find versions with warm melted butter.

Look also for creamy clam chowder, fried clams and haddock, and wild Maine blueberries in pies, muffins and pancakes in late summer.

For local produce, cheese, bread and seafood, visit the Portland Farmers' Market, held on Saturdays in Deering Oaks Park during the warmer months and on Wednesdays in Monument Square.

Where to stay

The Old Port and the waterfront are the most convenient bases, putting you within walking distance of restaurants, shops and the ferry terminal. They suit first-time visitors and couples, though they are the busiest and most expensive areas in summer.

The West End, with its grand nineteenth-century homes and quiet tree-lined streets, is good for travelers who want a residential feel and historic inns while still walking to downtown.

Best time to visit

Summer, from late June through August, is peak season, with warm days, cool evenings, every ferry and attraction running, and busy streets. Book accommodation and dinner reservations well ahead, especially on weekends.

September is many visitors' favorite month, with pleasant temperatures, warmer water and fewer crowds once schools are back.

Getting there and getting around

Portland International Jetport is only a short drive from downtown, with nonstop flights from several major East Coast and Midwest hubs. Many visitors fly into Boston instead and continue by road or rail.

Once you are here, the peninsula is very walkable, and the Old Port, Arts District and Munjoy Hill are all within about a mile of each other.

A suggested itinerary

First day

Spend the morning exploring the Old Port and the wharves, with a lobster roll for lunch.

Second day

Drive to Cape Elizabeth for Portland Head Light and Fort Williams Park in the morning. On the way back, stop at Spring Point Ledge Light and Bug Light in South Portland.

Third day

Take the ferry to Peaks Island and bike around the island, or ride the mail boat to see more of Casco Bay.

Practical tips

• Reserve dinner tables at popular restaurants in summer and on fall weekends, often weeks in advance.
• Pack layers and a light rain jacket; coastal weather changes quickly, even in July.
• Check seasonal opening dates for the Portland Observatory, Victoria Mansion and lighthouse museums.
• Look at the cruise ship schedule; on busy port days, explore the Old Port early or late.
• Wear sturdy shoes for brick sidewalks, cobblestones and the granite breakwater at Spring Point.
• Check the Casco Bay Lines schedule for the last return ferry before heading out to the islands.

Find local businesses in Portland on WiserMap

From lobster shacks and bakeries to bike rentals for Peaks Island and local shops in the Old Port, browse Portland businesses on WiserMap to find locally owned places and plan your stops around the city.

Explore local businesses