Islands and Inlets: Maine Maritime Adventures

With thousands of miles of jagged coastline; countless rugged islands, inland lakes and ponds; a labyrinth of streams and rivers; and a culture still driven by nautical history, Maine is a place best discovered on the water. Whether pulling traps on a lobster boat, paddling deep-woods ponds in search of moose, or commuting between islands by mail boat, this adventurous Maine road trip offers a new experience on the water nearly every day. In the evenings, rest your head on dry land while listening to lapping water and loon calls from your secluded inn or lodge.

Portland

Days 1 & 2

You’ll begin your Maine road trip adventure in Portland.  This lively coastal city is small by most measures, but it feels tremendously urban compared to the tiny towns and hamlets tucked into wooded wilderness and scattered along the coast. 

From your base in the Old Port District, spend your first afternoon exploring downtown’s cobbled streets and working wharfs before watching your first Maine sunset from Casco Bay as you stand-up paddle board or kayak with a local guide. This evening, head just outside of town to embark on a unique farm-to-table experience with a fieldside gazebo at Jordan Farms.   

The next morning, you’ll meet your guide at the pier and board the mailboat for an island cycling adventure. A  quick motor across Casco Bay will bring you to Chebeague Island where you’ll pedal along quiet roads lined with grand Greek Revival homes and simple rusticator cottages before looping back for lunch at a charming seaside inn. Hop back on the mailboat to reach Cousins Island and ride across the causeway connecting to the mainland. 

The Blue Hill Peninsula & Deer Isle

Days 3 & 4

It only takes a few hours to shoot directly up the coast, but this drive will be all about the journey. Foodies can stop at Wolfe’s Neck Coastal Farm to learn about innovative and sustainable coastal agriculture or grab lunch at our favorite under-the-radar lobster shack. Stretch your legs with a hike up Mt. Megunticook or Mt. Battie with rewarding views of idyllic Camden and the islands of Penobscot Bay.

End your day on the wild and wonderful Blue Hill Peninsula, crossing the bridge to Deer Isle where your airy seaside cottage waits on a mossy perch beneath the pines. We’ll be sure to get you a table at the inn’s restaurant, where chef Devin Finigan showcases delicious local cuisine on her deck overlooking Goose Cove.

Spend a morning sea kayaking with your guide in the placid waters of Stonington Harbor, Maine’s top lobster port, before heading out to explore the inner ring of the Merchant Islands. Alternatively, hop  on the ferry for your first taste of Acadia while hiking on rugged and wild Isle Au Haut where fishing remains the primary occupation and the year round population count doesn’t break triple digits . 

Down East in Acadia National Park

Days 5 – 7 

Your Maine road trip continues north to Mt. Desert Island, the heart of Acadia National Park. Begin your exploration with a drive along the Park Loop, which provides plenty of opportunities to explore the bare mountain tops, cliffs, boulders, and ponds of this glacially formed island. This afternoon, you’ll set off on a hike to enjoy golden hour from the summit of iconic Cadillac Mountain, the highest point on the eastern seaboard, or one of Acadia’s lesser known peaks with great views of Bar Harbor and the surrounding islands.

The next day take the ferry to the Schoodic Peninsula, passing lighthouses, hidden coves, seaside mansions, and lobstermen hauling their traps. In the community of Winter Harbor, you’ll pick up your bikes, as well as a gourmet picnic, and set out to explore the peninsula’s tiny hamlets and charming byways. The Schoodic portion of Acadia National Park includes miles of hard-packed gravel bike paths, which offer spectacular views along their winding, wooded routes. After a picnic lunch on the cliffs, make your way back towards the harbor and meet your captain for a private boat journey down Frenchman Bay. You’ll visit an island wildlife refuge that is home to a variety of nesting seabirds, such as arctic terns, razorbills and black guillemots, but most notably is one of only a handful of Maine islands where endangered Atlantic puffins nest.

Take the morning for a cooling summer swim in one of Mt. Desert’s sheltered inland ponds. End your time in Acadia with a voyage aboard an authentic Maine lobster boat. You will haul traps and learn all about the industry that helps support coastal Maine. Pull up to a dockside island restaurant, accessible only by boat, where this local favorite that serves up lobsters harvested from the same waters you sailed today. 

Moosehead Lake & The Maine Highlands

Days 8 – 10

Leaving the coast, your drive deep into Maine’s interior will take you to the shores of pristine Moosehead Lake. Maine’s largest lake is dotted with over eighty islands and lined with cliffs, coves and deep shorelines that are perfect for swimming. This evening, you’ll enjoy dinner on the dock of your lakefront lodge as the light fades over the Longfellow Mountains. As darkness falls, slip out onto the lake’s calm black waters for a night of stargazing from a canoe. 

Make an early start today to set out on the water once again in search of Moosehead Lake’s namesake. Moose outnumber people three to one in Greenville, so your chances are good, especially with the help of your naturalist guide. Paddling along the swampy edges of secluded ponds is the best strategy to find these surprisingly elusive 1,000-pound creatures. In the afternoon, cool down at the base of a waterfall after exploring deep woods trails on foot.

For your final day in the wilderness, get your adrenaline pumping on the Kennebec River. In your private raft, you’ll surge through wild waters that were originally used to run logs downstream before innovative Mainers realized the rapids would just as easily support adventure seekers.  You’ll be soaked after navigating the Kennebec River Gorge, Big Mama Rapids and Magic Falls, so you may as well hop in for a swim on the lower section of the river as you watch for wildlife.

The South Coast and Kennebunkport

Days 11 & 12

Today, you’ll return to the coast. Finish your adventure in quintessential Maine fashion in the seaside community of Kennebunkport. You’ll be tempted to stay tucked away at Hidden Pond, a luxurious escape set on sixty acres of enchanting woodland on the edge of town, but be sure to make time to wander through the shops and galleries around Dock Square or to take a gentle oceanfront stroll out towards the Bush family estate on Walker’s Point. Have a final encounter with the chilly Atlantic Gooch’s beach before you toast final Maine evening with one last local brew or ice cream cone. 

The next day, you’ll end your trip with a quick drive up the coast as you return to Portland. 

From The Magazine

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