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Boothbay Harbor to Bar Harbor Bike Tour

Itinerary

What’s Included

Reviews

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2026 Dates

June & Sept

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7 Days
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Difficulty Level

Moderate/Advanced - My Bike Has A Name

Ride the Maine Coast, from Boothbay Harbor to Bar Harbor

A weeklong guided journey from working harbors to Acadia National Park — long miles, quiet roads, and the kind of reward that only comes from earning it.

Tracing the Maine coast from Boothbay Harbor to Acadia National Park, this guided cycling tour follows quiet roads through working harbors, historic towns, and some of the state’s most dramatic shoreline. The route blends long, rewarding miles with carefully chosen moments of rest — lighthouse visits, island views, ferry crossings, and meals that feel well earned. From Pemaquid Point and Penobscot Bay to the quiet side of Acadia and the Park Loop Road, each day builds naturally on the last, creating a journey defined by progression, purpose, and a deep sense of having truly traveled the coast.

(Traveling to Portland during your trip to Maine? Explore our range of Portland Day Tours.)

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”
  • Log some epic miles
Pricing

Tour Price: $3,995 per person double occupancy
E-Bike Rental: $250
Single Supplement: $900

2026 Dates

June 21-27

September 13-19

* other dates available by request for groups of 4 or more *

 

Pickup/Drop Off
Portland, ME (PWM)

Itinerary

DAY 1 Boothbay Harbor to Pemaquid Point

Leaders will meet you at the visitor’s center in downtown Portland, Maine, on the first morning of the tour for the one-hour transfer to Boothbay Harbor. We begin our trip cycling stunning Ocean Point before pedaling to the charming village of Damariscotta. We end our day at the Pemaquid Point Lighthouse, where we enjoy a welcome wine and cheese reception before dinner at the elegant Bradley Inn.

    • Cycling: 48 miles | elevation gain 3,126 ft
    • Meals: Dinner
    • 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. Enjoy an optional visit to the farm where Andrew Wyeth painted the iconic “Christina’s World” before pedaling to Clark Island and our inn overlooking the ocean.

  • Cycling: 54 miles | elevation gain 3,316 ft
  • Meals: Breakfast & Dinner
  • Lodging: The Craignair Inn

DAY 3 Clark Island to Camden

You 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.  You finish your day in the picturesque town of Camden, where you enjoy a sunset sail on Penobscot Bay.

  • Cycling: 30 or 54 miles | elevation gain 2,797
  • Meals: Breakfast, Lunch, Dinner
  • Lodging: Blue Harbor House Inn

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. Here we’ll pause to enjoy a picnic lunch before a short transfer. Your ride continues along the western shore of Penobscot Bay and into the town of Castine where a lobster feast awaits.

  • Cycling: 53 or 63 miles | elevation gain 3,517 ft
  • Meals: Breakfast & Dinner
  • 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, our ride continues along miles of quiet coastal roads. You cycle along Eggemoggin Reach and into the town of Blue Hill before a transfer to Bar Harbor. An optional non-supported route will be offered for those who wish to arrive in Bar Harbor seated on the saddle of their bike.

  • Cycling: 40, 61, 77 or 100 miles | elevation gain 4,537 ft
  • Meals: Breakfast, Lunch
  • Lodging: First of 2 nights at The Pathmaker Hotel

DAY 6 The Quiet Side of Acadia

Today you cycle to the quiet side of Acadia National Park. The ride takes you through Northeast Harbor, along Somes Sound, and into the town of Southwest Harbor, where you pause for lunch. After lunch, you cycle to the Bass Harbor Light before following country roads back to Bar Harbor.

  • Cycling: 36 or 50  miles | elevation gain 3,538 ft
  • Meals: Breakfast, Dinner
  • Lodging: Final night at The Pathmaker Hotel

DAY 7 Cycling Acadia National Park

Wrap up a memorable week with an early morning spin on Acadia National Park’s famous Park Loop Road as it winds along the shore. Your choice whether or not you’d like to celebrate our week with a climb up Cadillac Mountain.

  • Cycling: 21 or 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
  • Most meals – including five dinners, six breakfasts, and two lunches
  • All taxes and gratuities for these meals
  • Entrance fee for Acadia National Park
  • Experienced Summer Feet Guides
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  • Sailing aboard a schooner
  • Hybrid or All-Road Bike Rental
  • Turn by turn directions using Ride with GPS
  • Van support including fresh water, ample snacks, and “relief rides”
  • Summer Feet Souvenirs – a cycling water bottle and t-shirt (available in men’s and women’s fit)
  • Alcoholic beverages are not included in the package price and are always at your discretion
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Sharon Kalember
★★★★★

The cycling was lovely, and there were gorgeous views around every corner. The towns we rode through were beautiful, and we took a lot of back roads, seeing things we wouldn’t normally get a chance to see.”

Paula Casey
★★★★★

I’ve been on many bike vacations with various companies, both domestic and international, and Summer Feet was by far my favorite.

Sherri Silverstein
★★★★★

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

Steve Weese
★★★★★

“We loved the trip. We’ve done a couple trips with Bicycle Adventures and and Bike Vermont. This was our favorite.”

Michael Brown
★★★★★

Five Stars to Rick (our guide) and the folks at Summer Feet Cycling. The ride was perfectly tailored to our group of nine middle aged individuals. The sights were terrific and the lobster role for lunch was the best I have ever eaten. Thanks for making our time in Maine a memorable experience.

Marsha Walton
★★★★★

Our Summer Feet cycle along the Maine coast was glorious. In early September, we had perfect weather. We cycled along breathtaking views. Then we caught our breath in quaint Maine towns and fishing villages. Each evening our luggage was waiting for us at a charming inn, where we were served breakfast before heading out the next morning. The Summer Feet staff were friendly and efficient. We will hope to plan another Summer Feet trip soon! Pedal The Coast

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