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Boothbay to Bar Harbor Self-Guided

Itinerary

What’s Included

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2026 Dates

May - Oct

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7 Days
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Difficulty Level

Moderate/Advanced - My Bike Has A Name

Marshall Point Lighthouse and the keepers house

Explore Maine. On Your Own Terms.

A seven-day self-guided cycling journey from Boothbay Harbor to Acadia National Park — coastal miles, historic villages, and the freedom to ride at your rhythm.

This self-guided Maine bike tour takes you from Boothbay Harbor to Acadia National Park, riding quiet coastal roads past working harbors, granite headlands, and historic villages. The pace is yours — stop when you want, take the scenic route, linger where it feels right. We handle the lodging, luggage transfers, and detailed navigation so you can focus on the ride and the satisfaction of discovering Maine under your own power.

Any questions about this tour itinerary? Please get in touch. Remember, if you want a tailored tour experience, please contact us about Custom Cycling Tours in Maine option. 

 

Highlights

  • Enjoy 7 days of Inn to Inn cycling along the Maine Coast
  • Explore charming towns and coastal villages
  • Discover hidden coves and stunning coastline
  • Enjoy a variety of Maine delicacies, from lobster and smoked salmon to fresh blueberries and the local favorite “whoopie pies”
Pricing

Tour Price: $2750 per person double occupancy

E-Bike: $250.00

2026 Dates

The Boothbay to Bar Harbor Self-Guided Tour can start on any Sunday from mid-May through mid-October

Pickup/Drop Off
Portland, Maine (PWM)

Itinerary

DAY 1 Boothbay Harbor to Pemaquid Point

Your Maine Adventure Begins

We handle the details. You just ride and enjoy.

From the moment you arrive, everything is ready — your bike is fitted and your adventure awaits. We’ll collect you in Portland for a comfortable one-hour transfer to the stunning harbor town of Boothbay. 

Begin your cycling journey at Ocean Point, where the Atlantic crashes against rocky shores, and pedal at your own pace through the charming village of Damariscotta — a place where locals still know each other by name. Your day ends in the shadow of Pemaquid Point Lighthouse, one of Maine’s most photographed lighthouses, where you’ll settle into your inn as the sun sets over the sea.

What You’ll Feel: The thrill of discovery without the stress. The freedom to stop when you want, linger where you love, and ride at your rhythm. Breathe deep, move freely, feel alive.

The Day:

  • Transfer: 1 hour 15 minutes
  • Cycling: 53 miles | elevation gain 3,297 ft
  • Meals: None (but dinner awaits at your inn!)
  • Lodging: The Bradley Inn

Local Insider Tip: Stop at the King Eider’s Pub in Damariscotta for a pint of Maine craft beer — it’s a local favorite and worth the detour.

 

DAY 2 Pemaquid Point to Clark Island

Where History Meets the Sea

Not a tourist — an explorer.

Today you’re riding through pages of history at your own tempo. At Pemaquid Harbor, where the English and French once battled for control of New England, you’ll see why this coast was worth fighting for. The views are breathtaking, the history is rich, and the stories practically tell themselves.

Continue through Waldoboro, an “off the beaten track” town that gives you a glimpse of authentic small-town Maine life. Here, you’re not just passing through — you’re connecting with a place that time nearly forgot. Take as long as you like. Your day ends on Clark Island, at an inn perched right over the ocean where the only sound is the rhythm of the waves.

What You’ll Feel: Like you’ve discovered Maine’s best-kept secrets. These aren’t sights on a checklist — they’re chapters in your own story. And you’re writing it at exactly the pace that feels right.

The Day:

  • Cycling: 64 miles | elevation gain 3,316 ft
  • Meals: Breakfast
  • Lodging: The Craignair Inn

Support the Local: Your stay at the Craignair Inn directly supports a family-owned Maine landmark that’s been welcoming travelers since 1928.

DAY 3 Clark Island to Camden

 Art, Culture, and Coastal Beauty

Earn the lobster roll. Savor the moment.

Begin your day in Spruce Head Spruce Point peninsula before cycling to Birch Point State Park and the spectacular Owls Head Lighthouse, standing guard over Penobscot Bay like it has for generations.

Then it’s on to Rockland — an eclectic village that punches way above its weight in culture. The Farnsworth Museum showcases an extensive collection of Wyeth Family art, while The Island Institute works to preserve Maine’s island communities. And the shops? Charming doesn’t even begin to cover it. You’ve got all the time you need to explore.

End your day in Camden, where mountains meet the sea and your inn welcomes you like family.

What You’ll Feel: The perfect blend of culture and adventure. Plus that post-ride glow that comes from knowing you’ve earned every bite of tonight’s dinner. And the satisfaction of having made every stop, every detour, entirely your choice.

The Day:

Art Lover’s Note: The Farnsworth Museum is world-class. If you love American art, plan for an extra hour here — you set the schedule.

DAY 4 Camden to Castine

 Rolling Hills and Timeless Villages

Safe, supported, and designed for every rider.

The rolling hills of Camden unfold into miles of quiet country roads — the kind you dreamed about when you imagined “cycling through Maine.” Pass through the summer community of Bayside and into coastal Belfast for a well-deserved lunch before a short transfer by van.

Your ride continues along Penobscot Bay’s eastern shore to Castine, a historically rich town that has flown the flags of four nations. Walking (or cycling) through Castine is like turning back the pages of pre-colonial American history. Explore at your leisure — there’s no rush.

What You’ll Feel: Confidence. By day four, you’re not just riding — you’re thriving. Many travelers arrive unsure if they can handle the miles. With each day, you prove to yourself: Yes, you absolutely can. And you’re doing it on your own terms.

The Day:

  • Cycling: 55 miles | elevation gain 3,559 ft
  • Meals: Breakfast
  • Lodging: The Castine Inn

History Buff Heaven: Castine has been occupied by four different countries. Take a self-guided walking tour before dinner — the town is an open-air history museum, and you’re the curator of your own experience.

DAY 5 Castine to Bar Harbor

Gateway to Acadia

The ride that brings you closer.

Your morning begins exploring Castine’s storied streets at whatever pace suits you, before continuing along miles of quiet coastal roads toward Mt. Desert Island and the legendary town of Bar Harbor — gateway to Acadia National Park.

This is the kind of ride that brings people closer. Whether you’re cycling with a spouse, best friend, or parent, you’ll come away with stories you’ll be telling for years. These miles become memories, and memories become your legacy. The beauty of self-guided? You can stop for photos, snacks, or spontaneous exploring whenever the moment strikes.

What You’ll Feel: Anticipation. Bar Harbor buzzes with energy, and Acadia National Park awaits. Tonight, you’ll celebrate how far you’ve come — both literally and figuratively — knowing you navigated every turn yourself.

The Day:

Celebration Stop: Bar Harbor has incredible dining. After five days of riding, you’ve earned the best lobster dinner of your life. Take your time choosing — the evening is yours.

DAY 6 The Quiet Side of Acadia

 Discover What Others Miss

Travel that gives back to Maine.

While crowds flock to Acadia’s famous Park Loop Road, you’ll discover the “quiet side” — winding through charming villages to Southwest Harbor at your own rhythm. This is the Maine locals know and love: peaceful, authentic, and stunningly beautiful.

Take an optional ride to Bass Harbor Head Lightstation, where the lighthouse perches on a cliff above crashing waves. It’s one of the most photographed spots in Maine, yet on the quiet side, you might have it almost to yourself. Linger as long as you like — this is your day to design.

What You’ll Feel: Like an insider. By choosing to bike instead of drive, you’re connecting with Maine in a way that’s lighter on the planet and richer for your soul. Every pedal stroke supports local communities and preserves the beauty you came to see. And the freedom to explore on your own terms? That’s priceless.

The Day:

Insider’s Secret: Southwest Harbor is where Mainers go when they want to escape. Grab a coffee at Common Good Soup Kitchen — it’s community-run and delicious. Stay for an hour or five minutes. Your call.

DAY 7 Cycling Acadia National Park

 The Grand Finale

Stories you’ll tell for years.

Seven days ago, you arrived with your bike and your curiosity. Today, you cap off this unforgettable journey by cycling Acadia National Park’s famous Park Loop Road as it winds along the rocky shore.

And then — the grand finale — a climb up Cadillac Mountain, the highest point on the North Atlantic seaboard. Ride as far up as you’d like, stop for photos whenever inspiration strikes, and savor the accomplishment. This wasn’t just a bike tour. This was a transformation — and you navigated every mile of it yourself.

From here, it’s a comfortable transfer back to Portland, where your adventure began. But the memories? Those travel home with you. Along with the confidence that comes from knowing you explored one of America’s most stunning coastlines entirely on your own terms.

What You’ll Feel: Accomplished. Proud. Alive. And already planning your return.

The Day:

  • Cycling: 27 miles | elevation gain 2,624 ft
  • Meals: Breakfast
  • Transfer: approximately 3.5 hours

Final Thought: You came to see Maine. You leave having experienced it with every sense — the salt air, the taste of fresh lobster, the feeling of freedom on two wheels, and the warmth of connection with the people and places that make this coast unforgettable. All at your own perfect pace.

Please Ask a Question or give us a call at 1.866-857-9544 if you have any questions.

What's Included

  • Six nights’ lodging
  • All lodging taxes and gratuities
  • 6 breakfasts
  • Choice of hybrid or all road bike
  • Detailed route notes and maps and turn by turn navigation using Ride with GPS (no cellular data needed)
  • Daily Luggage Transfers
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  • Emergency Support
  • Summer Feet Souvenirs – cycling water bottle and t-shirt (available in men’s & women’s fit)
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Colleen H from Massachusetts
★★★★★

It was an exhilarating experience but extremely relaxing at the same time. I’ve fallen in love with cycling.

Shari S from Toronto
★★★★★

It was hands down the most terrific cycling trip we have ever been on, you looked after everything to perfection.

Frequently asked questions

Who is this tour best suited for?

The Boothbay to Bar Harbor self-guided tour is ideal for travelers who want an immersive cycling journey along Maine’s coastline and enjoy the rhythm of riding day after day.  It’s especially appealing to riders seeking a strong sense of progression and accomplishment.

The Boothbay to Bar Harbor self-guided trip is moderately to highly active, with longer daily rides than some of our other self-guided tours.  Routes are scenic and thoughtfully planned.  Riders should be prepared for sustained cycling over the course of the trip.  Daily mileage ranges from 53 to 64 miles most days.

There is only one (really fabulous) restaurant on Spruce Head – that’s the Causeway Restaurant at the Craignair Inn. We recommend you make a reservation! If the menu at the Causeway doesn’t float your boat, then you can always pick something up at one of the small sandwich shops along your ride and have your own picnic dinner.

911 is the emergency number here in Maine. In a bonafide emergency, please call 911 first.

If you are used to riding your bike on hills, then you’re likely to find the hills very manageable. If you are used to riding on a very flat terrain, then you might find the hills of coastal Maine challenging. You can always rent an e-bike if the idea of climbing hills feels like an obstacle to enjoying your vacation.

The Boothbay to Bar Harbor itinerary is *the* original self-guided cycling challenge developed by Summer Feet Cycling! It’s a week of demanding (yet totally do-able) coastal rides that build toward a dramatic finish atop Cadillac Mountain in Acadia National Park.

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