Portland is Maine's most populous city, and it's well worth spending a few days. It's renowned for its local food, beer and art scene, which alone is enough to keep you busy. Located in Casco Bay, the city has a working waterfront with daily boat and fishing tours and ferry rides. If you're thinking of staying a few days, check out one of many downtown hotels or Airbnbs. We recommend staying close to the Old Port or eastern promenade.
Take a ferry from the Maine State Pier on the waterfront in Portland to one of Maine's many islands, like Peak's Island. The ferry takes 15-20 minutes. Explore and rent bikes to ride around.
Maine is known for its lighthouses and the view on the coast is breathtaking. There are always a few food trucks selling lobster rolls nearby the lighthouse in Fort Williams Park. After, grab an ice cream or blizzard at Red's in South Portland.
The Portland Museum of Art is the largest and oldest public art institution in Maine. Wonderful collection of artists from the state and around the world.
Oysters, lobster rolls on Asian-style steamed buns, crudos, James Beard award-winning chef. Doesn't take reservations and is super popular, but worth the wait. Grab a drink at the bar or head to Tomaso's Canteen across the street and down the alley while you wait.
No frills seafood with real Mainers right on the waterfront in Portland. Chowder and oysters are top picks. You'll get fishermen coming straight off the boat. Everyone is a little rough around the edges, but the food is fantastic.
Arguably the best restaurant in Portland. You can't order a bad meal. The pork loin and mashed potatoes are family favorites. They have also a sister restaurant, Street & Co., which is excellent, as well.
Duckfat fries, milkshakes and local beer. Perfect for a mid-day snack.
The Front Room is a great pick for brunch, lunch or dinner. Expect American comfort food. It always delivers, as do its sister restaurants The Corner Room (Italian) and The Grill Room (steakhouse).
Known for farm-to-table Japanese food + fresh Maine seafood.
Great American farmhouse style beer, great vibes. Sit in the tap room or grab a growler and head up Munjoy Hill to have a beer overlooking the harbor on the eastern promenade.
Warehouse brewery on the Fore River not far from downtown Portland. Good beer, patio seating and people watching.
Potato donuts that sell out daily. There are a few locations around Portland.
The freshest local seafood in a garage, outside of downtown Portland. Hasn't changed a bit in 20 years. Locals' favorite.
Longstanding Maine brewery that helped put the scene on the map. Tours 7 days/week, specializing in Belgian-style beers.
Award-winning American-style ales in Freeport (before you get to the Outlets). Try a flight if there's a food truck or grab some bottles and head to Harraseeket Lunch & Lobster on the water.
Takeout window with picnic tables right on the water in Freeport. Best eaten with Maine Beer Co. brews (Harraseeket is BYOB). Don't miss the fish & chips, especially the fried haddock.
Cute beach town on the southern coast of Maine. Rent kayaks for the ocean or river, hang out on the beach, wander around the downtown shops or take a drive up the coast admiring the beautiful homes.
If you're looking to extend your stay beyond a long weekend, consider a trip up the coast to explore Acadia National Park, a 47,000-acre state park on Maine's Mount Desert Island. Great hiking and camping or opt to stay in Bar Harbor at one of the many hotels or rentals. Note that this area will be very busy with lots of tourists during Labor Day weekend.