Boothbay to Bar Harbor Self-Guided

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  • 7 Days
  • 2023-2024 DatesMay - Oct
  • Difficulty LevelModerate/Advanced - My Bike Has A Name
Pedal the Coast

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. 

What's Included

  • Six nights’ lodging
  • All lodging taxes and gratuities
  • 6 breakfasts
  • Entrance fee for Penobscot Narrows Bridge
  • Detailed route notes and maps and turn by turn navigation using Ride with GPS (no cellular data needed)
  • Daily Luggage Transfers
  • Emergency Support
  • Choice of regular or flat bar road bike
  • Summer Feet Souvenirs – cycling water bottle and t-shirt (available in men’s & women’s fit)


  • 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 “whoopee pies”

Pick Up/Drop Off

Portland, Maine (PWM)

2023-2024 Dates

Self-Guided Tours can start on any Sunday


$2595.00 per person double occupancy



Day 1Boothbay Harbor to Pemaquid Point

Leaders will collect you in Portland, ME on the 1st 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 the inn in the shadow of the Pemaquid Point Light.

  • Cycling Options: 45 miles Elevation Gain 3126 ft
  • Lodging: The Bradley Inn
  • Meals: None

Day 2Pemaquid 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: 54 miles Elevation Gain 3316 ft
  • Lodging: The Craignair Inn
  • Meals: Breakfast


Day 3Clark Island to Camden

Begin your ride 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.

  • Cycling Options: 30 or 53 miles Elevation gain 2797 ft
  • Lodging: The Hartstone Inn
  • Meals: Breakfast


Day 4Camden 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 Options: 29 or 53 miles Elevation gain 3517 ft
  • Lodging: The Castine Inn
  • Meals: Breakfast


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, your ride continues along miles of quiet coastal roads before cycling onto Mt Desert Island and to the town of Bar Harbor.

  • Cycling Options:  52  miles Elevation gain 3616 ft
  • Lodging: First of 2 nights at The Sand Bar Cottage Inn
  • Meals: Breakfast


Day 6The 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.

  • Cycling Options: 36 or 50 miles Elevation gain 3538 f to 3800t
  • Lodging: A second night at The Sand Bar Cottage Inn
  • Meals: Breakfast

Day 7 Cycling Acadia National Park

You end 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 Options: 24 or 30 miles Elevation gain 2601 ft
  • Meals: Breakfast

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


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