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  • Working waterfront of Portland, Maine
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    Portland: City Bursting with Adventure

  • Family enjoying a beautiful day at Ferry Beach near Old Orchard Beach, Maine
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    Old Orchard Beach: Bustling Vibes on the Water

  • Aerial view of Damariscotta, Maine
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    Damariscotta: Plenty of Enjoyment Away from the Ocean

  • Kayakers taking in the stunning scenery in Peaks-Kenny State Park in Maine
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    Moosehead Lake: Basecamp for Epic Maine Outdoors

Portland Head Light overlooking Casco Bay in Cape Elizabeth, Maine
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Outdoor Fun in Maine: On and Away from the Coast

By Kelly Larson

  • Route distance:
    412 km
  • Suggested Time:
    1-2 weeks

Experience the many sides of Maine, from its iconic coastline and picturesque lighthouses to epic inland sights and adventures.

The largest state in New England and the northeasternmost in all the USA, Maine is as geographically diverse as it is beautiful. Along the coast, you’ll find picture-perfect lighthouses, quaint seaside towns and charming seafood restaurants serving some of the country’s finest fresh lobster. Maine’s coastline is a sight to behold, but there’s plenty more adventure and natural beauty to enjoy as you head inland. Unforgettable hiking, craft breweries and cideries, colorful fall foliage and striking mountain vistas are only the beginning. Hop in the car, fire up your favorite playlist and get ready for a road trip you won’t soon forget.

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Working waterfront of Portland, Maine
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Portland: City Bursting with Adventure

After flying into Portland International Jetport and picking up your rental car, head just 7.5 kilometers east to the city center. Making your way across historic cobblestone streets and through neighborhoods alive with street art, you’ll feel the sense of old-world-meets-new that Portland is known for. As the largest city in Maine, it’s not only teeming with creature comforts, but also a host of outdoor activities to enjoy. Dubbed one of the most bikeable cities in the USA by numerous publications, you don’t want to miss the opportunity to explore this seaside metropolis by bike. A vast network of paved trails connects visitors to greenspaces, attractions and entertainment. Want to check out the city and nearby attractions by water? Take a ferry from Old Port to one of Casco Bay’s magical islands to stroll across beaches, tour historical sights and take in the Instagram-friendly mystique of Maine’s famous lighthouses. Get to Peaks Island for an unforgettable bike ride around perimeter of the sandy paradise on the Peaks Island Loop. After touring the area by bike and sea, be sure to make time for a leisurely stroll through Portland’s walkable downtown to enjoy the sights and sounds of the city. And when you’re eventually ready to trade in the urban scene for something a bit more quaint, it’s time to hit the road and set a course for the lively beach town of Old Orchard Beach.

32 km
0.5 hour by car
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Family enjoying a beautiful day at Ferry Beach near Old Orchard Beach, Maine
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Old Orchard Beach: Bustling Vibes on the Water

Getting to the beach town of Old Orchard Beach from Portland is about as quick and easy as it gets. The most direct route is to hop on Interstate 95 and head about 25 minutes south. Avid sightseers may want to extend the experience a bit by taking the state highways that hug the coast and meander by multiple state parks, picturesque beaches, a seaside amusement park and scenic coastal towns like Cape Elizabeth. Whether you choose to stay on the coast in Old Orchard Beach or in one of the nearby towns in the region, there are countless places to stay. Charming bed and breakfasts. Historical inns. Beachfront resorts. They’re all ready and waiting to serve as your basecamp for exploring the area’s beaches and nearby outdoor attractions. One such attraction is Ferry Beach State Park. Less than 6 kilometers south of Old Orchard Beach, the public recreation area is home to forested nature trails, freshwater fishing holes, rolling streams and white sand beaches. After a leisurely hike, head back to Old Orchard Beach for a drink at a craft brewery and lunch at one of the many beachfront lobster restaurants the area is known for. Once you’re recharged and ready to go again, make for the Saco River to experience all it has to offer. Float through its clear waters by canoe, kayak or stand-up paddleboard, stopping along the way to rest on sandy beaches.

114 km
1.5 hour by car
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Aerial view of Damariscotta, Maine
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Damariscotta: Plenty of Enjoyment Away from the Ocean

It’s time to get to your next stop, take Interstate 95 north to state Highway 1 before arriving at your next destination: The town of Damariscotta. Known as the “Oyster Capital of New England,” this town is quintessential Maine. If you’re spending the night, there are several boutique inns and cabins nearby. When you’re not visiting the area’s must-see attractions, walk to coffee shops, breweries and seafood shacks while breathing in the brackish air sweeping in from the Damariscotta River. Regardless of how long you stay, you’ll want to take a guided tour through one of the area’s oyster farms where you’ll learn to find and cook your own oysters. There are multiple stops of the Maine Oyster Trail in Damariscotta and surrounding area, so come hungry! No trip to the area would be complete without a cruise on the breathtaking Damariscotta River. Hop aboard as your captain takes you to view local seal colonies by day or whisks you down the river at sunset while you sample the town’s famous oysters paired with outstanding wines. After your magical river adventure, head back to your accommodations and try to get some sleep, because the final leg of your journey is going to take you away from the coast and into some of the most stunning natural landscapes in the USA.

266 km
3.75 hours by car
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Kayakers taking in the stunning scenery in Peaks-Kenny State Park in Maine
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Moosehead Lake: Basecamp for Epic Maine Outdoors

After heading 266 kilometers north on Interstate 95, you’ll arrive at Moosehead Lake – Maine’s largest lake and your jumping-off point for endless outdoor adventures throughout the surrounding areas. Dotted along the lake’s serene shores, you’ll find well-appointed lodges, cozy cabins and elegant resorts to choose from. Moosehead Lake itself is the perfect place to swim, hike and view wildlife like moose, bears and beavers. Difficult as it may be to leave such a special place, the many wonders of Peaks-Kenny State Park are calling. One of Maine’s 32 state parks, Peaks-Kenny is nestled along the shores of Sebec Lake. A nature-lover’s paradise, the 340-hectare park offers unparalleled boating, fishing, hiking and swimming opportunities. On your way back to Moosehead Lake from the park, you’ll cross over sections of the world-famous Appalachian Trail which spans over 3,540 kilometers from Georgia to Maine. When it’s time for your grand outdoor adventures through the great state of Maine to come to a close, catch a flight home back at the Portland International Jetport or from Bangor International Airport southeast of Moosehead Lake.