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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

The journey begins in Portland, where you’ll meet your leaders and travel north to Boothbay Harbor as the coast slowly takes over. By the time you arrive, the noise of daily life has already started to fade.

Your first ride traces Ocean Point, where the Atlantic presses close and the road seems to hover between granite and sky. From there, you continue on toward the working village of Damariscotta, a place shaped by tide, trade, and time.

The day finishes at Pemaquid Point Lighthouse, standing firm at the edge of the continent. As the light softens, you’re welcomed with wine and cheese before settling in for dinner at the elegant Bradley Inn — a fitting end to a first day that announces, clearly, that this is no ordinary week.

    • Cycling: 48 miles | elevation gain 3,126 ft
    • Meals: Dinner
    • Lodging: The Bradley Inn

DAY 2 Pemaquid Point to Clark Island

This morning begins with history beneath your wheels.

You ride through Pemaquid Harbor, once contested ground between empires, where the English and French fought for control of New England. From there, the route slips inland toward Waldoboro, an off-the-radar town that offers a glimpse of small-town Maine as it still exists today.

There’s time for an optional visit to the nearby farm that inspired Andrew Wyeth’s Christina’s World — a quiet moment that adds depth to the landscape around you. The day finishes with a ride down a rural dead end road toward Clark Island, where the ocean reappears and your inn looks out over open water.

By evening, the miles feel substantial — and deeply satisfying.

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

DAY 3 Clark Island to Camden

You start the day exploring the quiet peninsula of Spruce Point, where the roads feel tucked away from everything else.

From there, the ride carries you to Birch Point State Park and on to Owls Head Light, standing watch over Penobscot Bay. The scenery opens wide as you approach Rockland, an eclectic harbor town known for its creative spirit and maritime roots.

Spend time at the Farnsworth Museum, wander the galleries and shops, or simply enjoy the working waterfront before continuing on to Camden. As the day winds down, you step aboard a sunset sail on Penobscot Bay — trading pedal strokes for wind and water as the hills catch the last light of day.

  • 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

The morning begins with a ride through Castine, a town that has flown the flags of four nations and still carries that layered history in its streets and architecture.

Leaving town, you follow miles of quiet coastal roads along Eggemoggin Reach, with views that stretch wide across the water. The route leads you into Blue Hill, where the pace slows before a transfer to Bar Harbor.

For those who want to stay in the saddle longer, an optional non-supported route offers the chance to ride all the way onto Mt Desert Island and the town of Bar Harbor — a long, rewarding day that you are certain to feel proud of.

  • 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 explore Acadia’s quieter, less-traveled side.

Our route carries you through Northeast Harbor, along Somes Sound — the only fjord-like body of water on the U.S. East Coast — and into Southwest Harbor, where you pause for lunch by the water.

In the afternoon, you ride to Bass Harbor Light, then follow country roads back toward Bar Harbor. It’s a day defined by contrast: calm stretches, long views, and the feeling of having experienced something most visitors miss entirely.

  • 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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