One of our staff meets you at our waterfront pick-up location in Portland and shuttles you north along the coast to your first inn. Once settled, you roll out on quiet coastal roads toward the working fishing village of Port Clyde, where lobster boats still set the rhythm of the day. From there, you continue to Marshall Point Light, standing at the edge of the Atlantic. You might recognize it from Forrest Gump, but in person, it’s unforgettable for entirely different reasons. The riding is relaxed, the scenery is stunning, and there’s no rush to be anywhere but right where you are. The afternoon is yours. Stretch out on the inn’s lawn with the ocean in view, or head out for a walk on the nearby Clark Island trails as the light softens and evening settles over the coast. • Elevation 1,200ft • Transfer: 1 hr. and 45 min.

Meals:  Nil

You start the day tracing the edges of Spruce Head before turning east along a string of quiet roads that feel made for bikes. Today’s route carries you to Birch Point State Park, then on to Owls Head Lighthouse, standing watch over Penobscot Bay. It’s one of those places where most people stop talking without realizing it. Take your time here. You’ve earned it. From there, the ride leads you into Rockland, a lively harbor town known for art, boats, and good food. Spend the afternoon exploring the Farnsworth Museum, browsing galleries and shops, or simply sitting near the water, watching the harbor come and go. • Elevation Gain 1,230 ft

Meals:  B

This morning begins on the water. An early ferry carries you across Rockland Harbor with wide views of the Camden Hills and the open bay ahead. When you step onto the island of Vinalhaven, things slow in the best possible way. Spend the day riding quiet island roads, wandering the small downtown, and getting a glimpse of what year-round island life looks like. There’s time to swim in an old granite quarry, explore the island’s back roads, visit the lighthouse on the northwest tip, or simply enjoy the feeling of being someplace most visitors never reach. You return to Rockland by ferry in the afternoon, with salt on your skin and a full day behind you. • Elevation Gain 1,300 ft

Meals:  B

Today is about options, and that’s the beauty of self-guided travel. The ride from Rockland to Camden is short and scenic, just thirteen easy miles along the coast. Once there, you decide how the day unfolds. Ride farther into the hills for sweeping views, or skip the bike altogether and wander Camden’s harbor, shops, and cafés. Sailing and kayaking are also options if you’re feeling adventurous. Camden has a way of pulling people in. Enjoy your time in town, on your schedule and at your pace. • Elevation Gain 770 - 2,050 ft

Meals:  B

This morning, one of our staff transfers you from Camden to Bar Harbor and the entrance to Acadia National Park. Then comes one of the greatest rides anywhere. Car-free, gently graded, and designed to be traveled slowly, Acadia’s Carriage Roads wind through pine and birch forests, cross graceful stone bridges, and explore the interior of Acadia National Park. Built by John D. Rockefeller Jr. so people could experience the park without the noise and air pollution of the newly popularized automobile, they still deliver exactly that. It’s peaceful, immersive riding, the kind that makes you forget how far you’ve gone until you stop. • Elevation Gain 1,470 ft

Meals:  B

Today’s ride traces Acadia’s dramatic coastline along Park Loop Road, where the land drops sharply into the sea and the views keep pulling you toward the water. Before reaching Jordan Pond, you leave Park Loop Road for a steady climb up Day Mountain along the only Carriage Road with a mountaintop finish. From the summit, the Cranberry Islands spread out across the bay before you descend toward the heart of the park. Lunch at Jordan Pond House is the perfect opportunity to stretch your legs, refuel, and relax off the bike. The popovers are legendary, and after this morning’s ride, you’ve earned them. Return to Bar Harbor via the Carriage Roads, savoring more car-free miles and wooded scenery. • Elevation gain 1,120

Meals:  B

Your final morning offers a choice because that’s what this week has been about all along. If you want a gentle goodbye, ride more Carriage Roads on the Witch Hole Loop, passing beaver dams, quiet ponds, and stretches of road that feel tucked away from everything else. If you’re craving one last challenge, ride from town to the summit of Cadillac Mountain, the highest point on the eastern seaboard, where the coast stretches out in every direction and the week comes full circle. However you choose to finish, you’ll leave knowing you didn’t rush this place. You lived it, at your pace and on your terms. • Elevation Gain 1,570 ft

Meals:  B