Weekend Adventure Itinerary to Portland, Maine

Portland, Maine, is the state’s southernmost urban hub and an artsy hybrid of coastal charm and cobble stoned streets. While other parts of Maine (like Acadia) are cherished for remote wilderness, Portland is a bustling city filled with rugged beaches, breweries, and historic icons.

Check out our weekend itinerary to maximize your time in Portland.

Saturday

Get the weekend started by hopping on a tour of Casco Bay Islands. Take a ferry, private boat, or opt for a paddleboarding or kayaking tour of the islands. However you choose to explore, be sure to see this diverse archipelago off Portland’s coast.

After touring the islands, head back to the mainland and check out the Portland Observatory. Take in the panoramic harbor views from this historic 1807 landmark. For even more history, be sure to check out the Victoria Mansion - one of the country’s best-preserved homes of the 19th century. End your day with a cold one at the local Allagash or Rising Tide Breweries.

Sunday

Take an easy jaunt along Fore River Sanctuary Trail— a 5.6-mile trail that covers some of Portland’s most diverse terrain, taking hikers past the city’s only waterfall and salt marshes. Popular for mountain biking in the summer, and cross-country skiing in the winter, this trail is also a great spot for birdwatching.

Spend the afternoon by the sea like a local at Willard Beach before exploring Old Port, the city’s historic downtown. Then make your way to Commercial Street to grab food and meander along the cobblestoned road in search of the perfect souvenir (blueberry maple syrup, anyone?).

Make it your own

Check out the featured adventures below for even more great Portland adventures to add to your weekend itinerary. There really is no right way to do it, so make it you own and enjoy this incredible coastal town in all of its glory.

Beyond Portland

If you’re looking to spend more of your weekend in the great outdoors, here are a few suggestions.

Pleasant Mountain

Make the 1.5-hour drive from Portland to Pleasant Mountain for over 10 miles of trails around southern Maine’s tallest peak.

Booth Bay and Monhegan Island

For a dose of true New England island bliss, head to Booth Bay and catch a boat out to Monhegan Island. A favorite artist's retreat, this historic island is thought to be one of the first inhabited places in Maine.  

Bristol

Lighthouses, coastal walks, and LaVerna Nature Preserve. Spend a few hours taking in the Maine vibes and scenery of this rocky seaside town.

Headline photo by Rapidfire. Published without modification under Creative Commons 2.0 Attribution 2.0 Generic license.