Maine Coast

Ocean Views and Tasty Foods
Price :
Duration :
5 days
Support :
Inn to Inn
Difficulty :
Level 2

Join us for five luxurious days on Maine’s spectacular coast! Starting and ending in Portland and staying right in the heart of the Old Port, we’ll want to explore the cobblestone streets and active piers before heading out by bike. We’ll first journey north, following bike paths and lanes out of the city to the college town of Brunswick, well known for summer productions from the Maine State Music Theater. From there, we’ll swing back south, with an overnight accessible only by boat that is sure to have a stunning sunset.

Continuing south, we’ll reach Kennebunkport where you might head for a stroll along one of the popular beaches that attract tourists all summer long. We’ll end our adventure by heading back to Portland via parts of the East Coast Greenway and U.S. Bicycle Route passing by a variety of lighthouses, including the world famous Portland Head Light. After a week of ocean views and delicious foods, we’ll wonder why we don’t travel by bike more often!

e-bike friendly: Click to read our FAQ

Photos by Nancy Pine | Jeana Bala | Kathy Wysocki | Brian Dame
Aug 14 - Aug 18, 2023
Space still available

"I had a wonderful time and am looking forward to more Adventure Cycling rides."


Day 1. Portland, Maine, 0 miles

We'll meet for the first time in the Old Port of Portland. A vibrant city, Portland boasts fantastic eateries, the Portland Museum of Art, and numerous piers. Come early to experience it all! We'll start our tour in the afternoon, meet all the members of our group and get ready for the great week ahead.

Day 2. Portland to Brunswick, 29 miles

On today's ride, we'll leave the hustle and bustle of the Old Port and make our way to Brunswick, home to Bowdoin College. Before we get there, be sure to stop along the way in Yarmouth and see Eartha, a three-story rotating globe of the world. You'll also want to stop in Freeport, home to L.L. Bean, great food, and even better ice cream. When in Brunswick, take the time to walk around Maine Street and Bowdoin College, ride out to Mere Point, or, if you're lucky, even get a chance to watch a performance at the Maine State Music Theater's summer location!

Day 3. Brunswick to Chebeague Island, 26 miles

While today is a fairly short day on the saddle, there is still plenty to do. We'll ride through Wolfe's Neck Center where you can take a tour of the coastal, organic farm, or take a quick detour and hike through Wolfe's Neck Woods State Park. For those looking for other off-the-bike adventures, consider scheduling a paddle with the L.L. Bean Adventure Center, and if you'd like more time on the bike, take a ride down to Bailey's Island. We'll spend the night on Chebeague Island, only accessible by boat, and a stunning location looking back at the mainland.

Day 4. Chebeague Island to Kennebunkport, 50 miles

Today, we'll head back south, passing by Portland and on to Kennebunkport, a classic Maine town right on the water. Along the way, we'll traverse along the East Coast Greenway, riding parts of the gravel path between Scarborough and Kennebunk. A small detour can bring you to Old Orchard Beach with a fun summer beach vibe and a historic pier.

Day 5. Kennebunkport to Portland, 46 miles

We'll end our week on the Maine coast by heading back up to Portland. Along the way, our route takes us by four (yes, four!) lighthouses: Two Lights, Portland Head Lighthouse, Spring Point, and Bug Light. Today is the day to take your time and make sure your camera is fully charged! Once we get back to the Old Port, we'll say goodbye to our new friends, but be sure to hit up a local microbrewery before heading home after a spectacular trip.


Additional Details
Start Location:
Portland, ME
End Location:
Portland, ME
Portland Intl. (PWM)
Total Days:
Riding Days:
Layover Days:
Tour Leader:
Average Daily Mileage:
Indoor (Inn to Inn)
Indoor Dining
Level 2
Single Supplement

Know before you go

Information for eBike riders:
Because every rider, eBike, road condition, and elevation profile is different, it is ultimately up to the participant to judge best whether their battery will last through each tour day. We recommend using pedal assist in its lowest setting or off when not needed to maximize battery range. Bringing a second battery is also recommended. Remember, there is no vehicle support on our inn-to-inn trips, and you would need to carry the extra battery along with all of your other things.