Trip Summary8 Days / 7 Nights June 18-25, 2027 |
When we think of Maine, we think of jaw droppingly beautiful coastlines, lobsters and lighthouses. We also think of quiet rural roads, sunrises and sunsets over the water, amazing vistas, down to earth, friendly people, and … a few hills to climb. Come join us for a ride along Maine’s coastline in June, 2027.
In addition to great riding, this tour also has lots of opportunity to shop, go kayaking, whale watch, hike or simply relax. And of course, you can’t go to Maine without enjoying a lobster dinner!
Each night we stay at lovely Bed & Breakfasts and small Inns.
| Day 1 | We will meet at the family-owned Berry Manor Inn in the town of Rockland. If you are flying into the area, Rockland is about 1.5 hours from either the Portland or Bangor airports. You can take a car service or rent a car to get from the airport to our start point. We will offer a range of loop rides. The shortest ride takes you just a few miles to the Rockland Lighthouse which is at the end of a mile long breakwater that you can walk. We will enjoy a group dinner in Rockland.![]() |
| Day 2 | We will offer loop rides from Rockland in the 30 to 55 mile range stopping at the Owls Head Transportation Museum with its working antique cars and airplanes, the Owls Head Lighthouse and the Marshall Point Lighthouse and Museum. Dinner is on your own in one of the many restaurants near our Inn.
Back in Rockland, be sure to check out the lovely shops. Also stop by the Farnsworth Art, Center for Maine Contemporary Art, Maine Lighthouse and Sail Power and Steam Museums, all within walking or short riding distance of our Inn. Also take a stroll on the Rockland Harbor Trail along the oceanfront. |
| Day 3 | Today we leave Rockland and ride to the town of Camden. In Camden, you can take a harbor cruise, go on a guided kayak tour, go fishing, or take a walk along the High Street Historic District. There is also an optional climb up Mount Battie for a great view of Camden and the harbor. We will plan a group dinner in Camden. |
| Day 4 | We offer a number of rides today ranging from 18 to 50 miles. You can also ride both the 18 and 50 mile routes to make it a metric century. The longer rides take the ferry from Lincolnville to Islesboro Island. You can gape at some of the summer cottages built here as you cycle through quiet roads. Dinner is on your own in many of the restaurants near our Inn. |
| Day 5 | We will continue to ride through quiet country roads, to the town of Searsport. The riding ranges from 35 to 54 miles. You will ride through the town of Belfast which sits along the Penobscot Bay where you will see an assortment of boats and yachts moored. Pedal along Belfast’s beautiful Harborwalk with its working shipyard, shops and restaurants. We end the day in the historic town of Searsport. Like Belfast, Searsport is known for its 19th century shipbuilding industry. You can also visit the Penobscot Marine Museum and Searsport Historic District. We will enjoy a group dinner in Searsport. If you drove to the start of the tour, we will shuttle you back to collect your car. |
| Day 6 | ![]() We will spend another day in Searsport. Our rides today take us north to Fort Knox historical park and the Penobscot Bridge and Observatory, the tallest bridge observatory in the world! We will enjoy a picnic lunch in the historical park. We will include another group dinner in Belfast. |
| Day 7 | If you have a car, you can continue the tour driving to Bar Harbor. If you do not have a car, we will transport you the 55 miles to Bar Harbor. Once we arrive at Bar Harbor, you will have the opportunity to walk around and grab a bite. Then in the mid-afternoon, we will take a whale watching cruise. We will enjoy a final group dinner.
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| Day 8 | The tour ends after breakfast. For legal and permitting reasons, we cannot guide you into Acadia National Park. However, you may want to extend your stay a couple of days to enjoy the famous carriage trails, Cadillac Mountain climb and Schoodic Peninsula riding at Acadia National Park.
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This is a seven night trip. The cost is $TBD per couple ($TBD per person). We limit the size of our tours to be no more than ten couples. We only accept couples on tandem bikes. Come join us!

What is included?
- Seven nights lodging (see the hotels/country inns below)
- Seven breakfasts
- One picnic lunch
- Five group dinners
- Admission to the Fort Knox historical park and Penobscot Bridge Observatory
- Routes
- Luggage transport
- Transport to pick up your car (if you drove to the start)
- SAG support (although we do expect you to ride the full routes, we are there to help with mechanical issues)
Note that we do not provide any bicycles. We expect that you have a tandem that is in good working order and that you are able to assemble your bike. If you do not have your own tandem, you can rent a coupled tandem from Mel at Tandems East. Mel sells tandems, so if you end up renting from them, you might get a discount if you purchase a bike from them. If you have a tandem that is not coupled it is possible to bring it, but you should make sure that all of your flights could handle the larger box. Shipping your bike using ShipBikes.com or BikeFlights.com is another option.
What is not included?
- Airfare
- Transportation to the Berry Manor Inn (start point)
- Meals, other than those mentioned above
- Alcoholic beverages
- Admissions to points of interest
What is the average mileage per day? Required rides range from 25 to 60 miles with the average mileage being 35. We believe that there is enough to see so that more miles may prevent you from fully enjoying the culture and beauty of the area. That said, we can work with you if you would like to ride more miles. Bear in mind, though, that we will not be providing SAG support for these extra miles, except in an emergency, if you are off the main route.
Here is a summary of the routes:
| Day | Route | Miles | Ascent |
| 1 | Rockland Breakwater Loop | 4.7 | 114 |
| Rockland Thomaston Loop | 14.1 | 561 | |
| Rockland Union Warren Thomaston Loop | 35.1 | 2120 | |
| 2 | Rockland Owls Head Loop Short | 35.1 | 1313 |
| Rockland Owls Head Loop Long | 54.6 | 2196 | |
| 3 | Rockland to Camden Short | 11.5 | 683 |
| Rockland to Camden with Magunticook Lake Loop | 28.8 | 1617 | |
| Rockland to Camden with Magunticook Lake Loop and Mt Battie | 35.1 | 2395 | |
| 4 | Islesboro Loop | 49.3 | 3005 |
| Camden Magunticook Lake Loop | 17.6 | 1057 | |
| Camden Magunticook Lake Loop w/Mt Battie | 23.8 | 1843 | |
| 5 | Camden to Searsport Short | 35 | 2000 |
| Camden to Searsport Long | 54 | 3000 | |
| 6 | Searsport Fort Knox Loop | 40.4 | 2608 |
Where will we be staying?
While this could change, here are the inns and hotels that we plan to stay in. If you are into large hotels, this isn’t the trip for you. We enjoy staying in smaller, family owned inns.
How do you get to the tour?
The nearest airports are Portland, ME and Bangor, ME. We recommend that you rent a car for the entire time of the tour. That may be less expensive than hiring a cab or Uber from the airports.
We will meet at the family-owned Berry Manor Inn in the town of Rockland. If you are flying into the area, Rockland is about 1.5 hours from either the Portland or Bangor airports. You can take a car service or rent a car to get from the airport to our start point. We will offer a range of loop rides. The shortest ride takes you just a few miles to the Rockland Lighthouse which is at the end of a mile long breakwater that you can walk. We will enjoy a group dinner in Rockland.
We will offer loop rides from Rockland in the 30 to 55 mile range stopping at the Owls Head Transportation Museum with its working antique cars and airplanes, the Owls Head Lighthouse and the Marshall Point Lighthouse and Museum. Dinner is on your own in one of the many restaurants near our Inn.

Today we leave Rockland and ride to the town of Camden. In Camden, you can take a harbor cruise, go on a guided kayak tour, go fishing, or take a walk along the High Street Historic District. There is also an optional climb up Mount Battie for a great view of Camden and the harbor. We will plan a group dinner in Camden.
We offer a number of rides today ranging from 18 to 50 miles. You can also ride both the 18 and 50 mile routes to make it a metric century. The longer rides take the ferry from Lincolnville to Islesboro Island. You can gape at some of the summer cottages built here as you cycle through quiet roads. Dinner is on your own in many of the restaurants near our Inn.
We will continue to ride through quiet country roads, to the town of Searsport. The riding ranges from 35 to 54 miles. You will ride through the town of Belfast which sits along the Penobscot Bay where you will see an assortment of boats and yachts moored. Pedal along Belfast’s beautiful Harborwalk with its working shipyard, shops and restaurants. We end the day in the historic town of Searsport. Like Belfast, Searsport is known for its 19th century shipbuilding industry. You can also visit the Penobscot Marine Museum and Searsport Historic District. We will enjoy a group dinner in Searsport. If you drove to the start of the tour, we will shuttle you back to collect your car.
We will spend another day in Searsport. Our rides today take us north to Fort Knox historical park and the Penobscot Bridge and Observatory, the tallest bridge observatory in the world! We will enjoy a picnic lunch in the historical park. We will include another group dinner in Belfast.
If you have a car, you can continue the tour driving to Bar Harbor. If you do not have a car, we will transport you the 55 miles to Bar Harbor. Once we arrive at Bar Harbor, you will have the opportunity to walk around and grab a bite. Then in the mid-afternoon, we will take a whale watching cruise. We will enjoy a final group dinner.
The tour ends after breakfast. For legal and permitting reasons, we cannot guide you into Acadia National Park. However, you may want to extend your stay a couple of days to enjoy the famous carriage trails, Cadillac Mountain climb and Schoodic Peninsula riding at Acadia National Park.