Around the Peninsula

Portland Bike Tour


Daily from mid-April through October at 10:30 am

Discover the rich history and stunning architecture of the Portland peninsula. Only 3.5 miles long and 3/4 miles wide the Portland peninsula is packed full of food, history and culture. This 2.5-hour tour will show you the best of the peninsula.

  • Cycle along the Ocean
  • Discover both the East and West Ends
  • Learn Portland’s Colorful History
  • Visit Some of the Local’s Favorite Spots

Price $79.00 per person



Your guide will meet you at our rental shop The Portland Encyclepedia located on the corner of Commercial and India Streets for the start of your tour.

The trip begins with an easy ride along the Eastern Promenade bike path. We will stop along the path to learn the history of Casco Bay and the Calander Islands as well as the life story of George Cleeve, Portland’s lawsuit-happy co-founder.

Next stop is Back Cove and Portland’s Deering neighborhood. Created in the 19 Century by wealthy residents angry about Portland’s rising property taxes.

From Back Cove you cycle into the Portland’s West End. Historically, the swanky part of town, the West End features broad tree-lined streets and beautiful homes from Victorian to Shingle Style.

Your last stop is the Old Port where your guide will share some of their favorite eating and drinking spots with you.

Participants must be 12 or older and should be comfortable cycling 8 to 10 miles on mostly flat terrain. Please wear athletic clothing.

Browse Trips


  • Use of bicycle and helmet
  • Guide


$79.00 per person


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This was a great way to see Portland. The guide, Norman was very knowledgeable about history and points of interest. Plenty if stops at points along the way. A nice ride at your pace. A good mix of trails and quiet neighborhood streets, with a few intersections, handled well by the guide. from TripAdvisor

We had a wonderful time on our recent bike tour. Our guide was knowledgeable and fun! Great way to learn more about the history of Portland, ME. from TripAdvisor