📌 Starting your Maine road trip in Portland? Read our complete One Week Maine Road Trip Itinerary — day-by-day from Portland to Bar Harbor and back.
Portland is Maine’s largest city and one of the finest small cities in the United States — a compact, walkable urban center on a peninsula jutting into Casco Bay, with a food and drink scene that has attracted national attention, a thriving arts community, a working waterfront that still smells like fish, and enough history layered into its brick streets and Federal-style architecture to reward days of exploration.
Walk the Old Port
The Old Port is Portland’s historic commercial district — 19th-century brick warehouses and commercial buildings along the waterfront, now housing the city’s finest concentration of restaurants, bars, boutiques, and galleries. Exchange Street, Fore Street, and the surrounding blocks are the heart of Portland’s pedestrian life. The buildings were rebuilt after the Great Fire of 1866, creating an unusually coherent streetscape of high-quality Victorian commercial architecture. The working waterfront is visible from the bottom of the Old Port’s streets — fishing boats, ferry terminals, and lobster wharves remind visitors that Portland is a real port city.
Visit the Portland Museum of Art
The Portland Museum of Art is one of the finest art museums in New England, with particular strength in Maine and American art — outstanding works by Winslow Homer, Andrew Wyeth, and Edward Hopper. The Homer collection is exceptional, including scenes painted at his studio at Prouts Neck. The 1983 Charles Shipman Payson Building by I.M. Pei is a modernist landmark. Open year-round — plan at least two hours for the permanent collection.
Eat Your Way Through the Food Scene
Fore Street — a wood-fired kitchen in a converted warehouse, one of the best restaurants in New England. Eventide Oyster Co. — nationally famous for its brown butter lobster roll, New England oysters, and exceptional natural wine list. Duckfat — Belgian-style fries cooked in duck fat, simple and brilliant. Becky’s Diner on the commercial fishing pier — the most authentic Portland breakfast experience, enormous portions at low prices where fishermen eat before heading out.
Explore the Eastern Promenade
The Eastern Promenade is Portland’s finest public space — a broad park along the East End ridge overlooking Casco Bay, with views across the bay to the Calendar Islands and the working harbor. The Promenade path runs about a mile with benches and picnic areas. East End Beach at the base of the hill is Portland’s in-city swimming beach. The surrounding Munjoy Hill neighborhood is one of Portland’s most dynamic.
Take a Casco Bay Ferry
The Casco Bay Lines ferry system connects Portland to six island communities — Peaks Island, Little Diamond, Great Diamond, Long Island, Chebeague Island, and Cliff Island. The 20-minute crossing to Peaks Island alone is worth it for the harbor views. Peaks Island has a ring road perfect for biking (bring your bike on the ferry), restaurants, a small beach, and the Fifth Maine Regiment Museum. Chebeague and Long Island are quieter and worth the longer ride.
Visit the Victoria Mansion
The Victoria Mansion (Morse-Libby House) is one of the finest surviving examples of Victorian interior decoration in the United States — a brownstone Italianate villa built 1858-1860 with an extraordinarily intact interior featuring original painted walls, carved woodwork, stained glass, and period furnishings. A National Historic Landmark open for tours May through October.
Drink Craft Beer
Portland has one of the highest concentrations of craft breweries per capita in the United States. Allagash Brewing is Maine’s most celebrated brewery — originator of Allagash White, with tours of the facility available. The East Bayside neighborhood has become the brewery district, with Oxbow, Rising Tide, Foundation Brewing, and Bissell Brothers all within walking distance of each other.
Portland Head Light
Portland Head Light in Cape Elizabeth, about 5 miles south of downtown, is the most photographed lighthouse in Maine. Surrounded by Fort Williams Park with extensive grounds, ocean views, and walking trails along the rocky coast. The Museum at Portland Head Light is housed in the former keeper’s quarters. The park is free and open year-round. The drive from Portland via Shore Road through Cape Elizabeth passes some of the finest coastal scenery in southern Maine.
Explore the Arts District
Portland’s Arts District on Congress Street has galleries, artist studios, the Portland Stage Company, the State Theatre (a restored 1929 movie palace), and the Maine College of Art. The First Friday Art Walk on the first Friday of each month from May through November opens galleries and studios throughout the district for free — one of the best ways to experience Portland’s arts community.
Getting Around Portland
Portland is compact and extremely walkable — the Old Port, Arts District, West End, and Munjoy Hill are all accessible on foot. Parking can be challenging in the Old Port — use the city’s parking garages rather than hunting for street parking.
Where to Stay
Portland has a wide range of lodging from the Portland Regency Hotel in the heart of the Old Port to boutique inns in the West End neighborhood. Browse our Portland lodging guide for the full list.
Plan Your Trip
Ready to visit Portland? Browse Portland lodging and start planning. For southern Maine destinations within easy reach, see our guides to Things to Do in Kennebunkport Maine and Things to Do in Ogunquit Maine. Heading further north? Read our Camden vs Bar Harbor comparison.
📌 Heading north from Portland?
Things to Do in Wiscasset Maine — about 50 minutes up Route 1.
Things to Do in Damariscotta Maine — about 1 hour up Route 1 and one of the finest midcoast stops.
Things to Do in Boothbay Harbor Maine — about 2 hours up the coast.
MaineGuide.com has been helping visitors plan their Maine trips since 1995.