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Boothbay to Bar Harbor Self-Guided

Itinerary

What’s Included

Reviews

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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

Exploring Maine’s Coastline:
A Seven-Day Cycling Adventure

The perfect bike tour for people looking for a fun, yet challenging, bike ride. During the weeklong Boothbay to Bar Harbor bike tour,  you will cycle 350 miles and enjoy over 22,000 feet of climbing. Starting in the picturesque town of East Boothbay, you will follow the contours of the coast, passing lighthouses, fishing villages, and charming towns all the way to Bar Harbor and Acadia National Park. In Acadia, you will finish your week of cycling by riding up Cadillac Mountain, the first place in the United States, to see the sunrise.

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

Leaders will collect you in Portland, ME on the first morning of your trip for the one hour transfer to Boothbay Harbor. Begin your trip cycling stunning Ocean Point before pedaling to the charming village of Damariscotta and to an inn in the shadow of the Pemaquid Point Light.

  • Cycling: 53 miles | elevation gain 3,297 ft
  • Meals: None
  • Lodging: The Bradley Inn

DAY 2 Pemaquid Point to Clark Island

Today you visit historic Pemaquid Harbor where the English and the French fought for control of New England during the French and Indian Wars. Later you cycle to the “off the beaten track” town of Waldoboro for a glimpse of small-town life in Maine before pedaling to Clark Island and your inn overlooking the ocean.

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

DAY 3 Clark Island to Camden

Begin your day exploring the quiet peninsula of Spruce Point before cycling to Birch Point State Park and the spectacular Owls Head Light as it stands guard over Penobscot Bay.  Your ride then takes you to the eclectic village of Rockland, home to the Farnsworth Museum of Art, which features an extensive collection of the art of the Wyeth Family, The Island Institute dedicated to preserving Maine’s Island communities, and a number of charming shops and galleries.

DAY 4 Camden to Castine

The rolling hills of Camden offer miles of riding on quiet country roads. Follow these roads through the summer community of Bayside and into the coastal town of Belfast and enjoy lunch before a short transfer. Your ride continues along the western shore of Penobscot Bay and into the historically rich town of Castine.

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

DAY 5 Castine to Bar Harbor

Your adventure continues as you explore the town of Castine, a historical gem that has flown the flag of four nations during its rich history.  Your morning ride through town is a journey through pre-colonial American history.  After exploring Castine, continue along miles of quiet coastal roads before cycling onto Mt Desert Island and to the town of Bar Harbor.

DAY 6 The Quiet Side of Acadia

Today you cycle to the quiet side of Acadia National Park, winding through charming villages to the town of Southwest Harbor. Take some time to explore the quiet side of Acadia and enjoy an optional ride to see the Bass Harbor Light.

DAY 7 Cycling Acadia National Park

Cap off a memorable bike tour cycling Acadia National Park’s famous Park Loop Road as it winds along the shore and end with a climb up Cadillac Mountain before your transfer to Portland.

  • Cycling: 27 miles | elevation gain 2,624 ft
  • Meals: Breakfast

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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