Portland’s transformation into a nationally recognized food city has been one of the most remarkable things we’ve watched happen in Maine over the past two decades. We were covering Portland when Fore Street was the only restaurant worth the trip — today the problem is choosing which of two dozen excellent options to try first.

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.

Portland in 24 Hours

One day is enough to see the best of Portland if you keep to the peninsula and pick one big outing. Check opening hours before you go, since several stops are seasonal.

Morning: Breakfast at Becky’s Diner on the commercial fishing pier, then walk the Old Port and the working waterfront.
Late morning: The Portland Museum of Art, or the Victoria Mansion if it is open for the season.
Lunch: A lobster roll. Our Maine lobster roll guide covers where to find a good one near Portland.
Afternoon: Choose one: drive out to Portland Head Light in Cape Elizabeth, or take the ferry to Peaks Island.
Evening: Watch the light go down over the bay from the Eastern Promenade, then dinner in the Old Port or a stop in East Bayside for a beer.

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.

Lobster on the menu? Here is how to eat a whole lobster, step by step.

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.

Parking, museum hours and the best photo spots are in our Portland Head Light visitor guide.

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.

More Things to Do in Portland

Climb the Portland Observatory

The historic maritime signal tower on Munjoy Hill offers views over the city and Casco Bay. It is open for tours in season, so check the current schedule before you go.

Visit the International Cryptozoology Museum

A small, quirky museum devoted to cryptids such as Bigfoot and the Loch Ness monster, and a favorite stop for families and anyone who wants something offbeat.

See the Harbor Lighthouses

Portland Head Light is the famous one, but the harbor has more. Spring Point Ledge Light and Portland Breakwater Light, known as Bug Light, are across the bridge in South Portland, and both are easy to reach and good for a short walk and a photo.

Sail on a Windjammer or Casco Bay Cruise

Seeing Portland from the water is one of the best ways to spend a summer afternoon. Take a sightseeing cruise in Casco Bay, or learn about a multi-day sail in our guide to Maine windjammer cruises.

Catch a Hockey Game

The Maine Mariners are Portland’s professional hockey team, a Boston Bruins affiliate, and check their official site for the home schedule. Older fans may remember the Portland Pirates, the city’s American Hockey League team, which played here from 1993 to 2016.

Free Things to Do in Portland

Walk the Old Port and the working waterfront.
Stroll the Eastern Promenade and visit East End Beach.
Explore Fort Williams Park and Portland Head Light (the museum has its own admission).
Walk out to Bug Light and Spring Point Ledge Light in South Portland.
Go to the First Friday Art Walk, May through November.

What to Do in Portland When It Rains

The Portland Museum of Art, which needs two hours or more.
The Victoria Mansion, if you are visiting between May and October.
The International Cryptozoology Museum, which is small and good with kids.
A brewery tour or tasting room in East Bayside, or the Allagash tour.
A show at the State Theatre or Portland Stage.
A long lunch in the Old Port: Eventide, Duckfat or a lobster roll.

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.

When to Visit Portland

Summer is the busiest season, and the ferries, cruises and the Victoria Mansion all run on seasonal schedules. Early fall is a good time for walking and eating without the peak crowds. Winter is quieter, and some seasonal attractions close, so check hours before you go. For the full picture, see our guide to the best time to visit Maine.

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. Traveling with children? See Portland with kids. Curious about the city’s past? Read the history of Portland, Maine. Thinking of moving here? See living in Portland.

Still choosing a base? Compare Portland with Bar Harbor, Kennebunkport, Freeport, Ogunquit or Camden.

Want to get out of the city? See our guide to day trips from Portland, sorted by drive time. 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 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.

📌 Day trip from Portland? Read our complete L.L. Bean Freeport Visitor Guide — just 17 miles north, open 24 hours a day.

📌 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. Driving up from Boston? See the Maine road trip from Boston guide.

📌 Eating in Portland? Read our complete Maine Lobster Roll Guide — Eventide’s brown butter roll and the Lobster Shack at Two Lights are both near Portland.

Things to Do in Portland, Maine FAQ

What are the best things to do in Portland, Maine?

Top things to do include exploring the historic Old Port with its cobblestone streets, shops, and renowned restaurants; visiting Portland Head Light (Maine’s oldest lighthouse, 1791) at Fort Williams Park in nearby Cape Elizabeth; taking a Casco Bay ferry to the Calendar Islands; touring the Portland Museum of Art; and sampling the city’s nationally celebrated food and craft-beer scene. The working waterfront and Eastern Promenade are also highlights.

Is Portland, Maine worth visiting?

Absolutely. Portland punches far above its size — it has one of the best food scenes in the country, a walkable historic Old Port, easy access to lighthouses and islands, and a lively arts and brewery culture, all on a scenic working waterfront. It’s Maine’s cultural hub and an ideal base for exploring southern and midcoast Maine.

How many days do you need in Portland, Maine?

Two to three days is ideal — enough to explore the Old Port, eat well, visit Portland Head Light and Fort Williams, take a Casco Bay island ferry, and use the city as a base for day trips to Freeport, Kennebunkport, or the coast. A long weekend covers the essentials comfortably.

What can you do in Portland, Maine for free?

Walk the Old Port and working waterfront, stroll the Eastern Promenade, visit East End Beach, explore Fort Williams Park and Portland Head Light, walk out to Bug Light, and go to the First Friday Art Walk (May through November).

What is there to do in Portland, Maine when it rains?

The Portland Museum of Art, the Victoria Mansion (May through October), the International Cryptozoology Museum, a brewery tour or tasting room, and a show at the State Theatre or Portland Stage are all good indoor choices.

About MaineGuide.com: MaineGuide.com has been helping visitors plan their Maine trips since 1995 — making us one of the longest-running and most comprehensive Maine travel resources on the web. Our guides are built on decades of firsthand Maine knowledge, local expertise, and a genuine love for the state.

Wondering how Portland, Maine compares with Portland, Oregon? See Portland, Maine vs Portland, Oregon.

Visiting at the holidays? Our Christmas in Maine guide covers the Polar Express and other seasonal events.

Things to Do in Portland Maine