Why Portland Punches Way Above Its Weight
Portland has 70,000 people and a food scene that rivals cities five times its size. It's been named "America's Foodiest Small Town" so many times the title has lost meaning. But beyond the restaurants, Portland is a working harbor city with a brick-paved Old Port, art museums, lighthouses, and easy access to islands you can explore by ferry.
What to Do
- Walk the Old Port. Cobblestone streets, historic buildings, shops, and restaurants packed into a few walkable blocks near the waterfront.
- Visit the Portland Head Light. Maine's most photographed lighthouse, in nearby Cape Elizabeth. Surrounded by a beautiful park with picnic spots.
- Take a ferry to Peaks Island. A 20-minute ride to a tiny island community. Rent a bike, ride the loop, get ice cream, take the ferry back. Half a day, well spent.
- Visit the Portland Museum of Art. Strong collection including Winslow Homer and Maine landscape painters.
Where to Eat
You could eat in Portland for a week without repeating yourself or having a bad meal. Highlights: oysters at Eventide, lobster rolls at any waterfront spot, fine dining at Fore Street, brunch on Munjoy Hill. The Portland food scene is best explored by wandering and getting lost.
Where to Drink
Portland has dozens of craft breweries within city limits — Allagash, Bissell Brothers, Foundation, Rising Tide, and many more. Most offer tasting rooms and tours. Plan a brewery crawl by neighborhood — East Bayside is the highest-density brewery area.
Practical Tips
- Use the Portland International Jetport (PWM) for easy access from anywhere in the country
- Stay downtown for walkability — most attractions are within 15 minutes on foot
- Make reservations for dinner at popular restaurants well in advance
- Combine Portland with day trips to Freeport (LL Bean, 20 min) and the Yorks (40 min)