Around the Peninsula

Day Trip
Day Trip

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  • 2.5 Hours Approx
  • 2023 DatesApr - Oct
  • Difficulty LevelEasy - Sounds Like Fun

Portland Peninsula Tour Overview

Discover the rich history and stunning architecture of the Portland peninsula.

Although only 3.5 miles long and 3/4 miles wide, the Portland peninsula is packed with food, history, and culture.

This 2.5-hour tour will show you the best of the peninsula, from the bike paths of the Eastern Promenade to Casco Bay and Black Cove. 

If you have any questions about this tour, please get in touch

What's Included

  • Use of bicycle and helmet
  • Guide


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

Pick Up/Drop Off

Tours depart at 10.30am from the Portland Encyclepedia located on the corner of Commercial and India Streets and return usually around 1 pm.

2023 Dates

Daily from mid-April through October 


$79.00 per person


Portland Peninsula Itinerary

Daily Tour

Your guide will meet you at our rental shop, The Portland Encyclepedia located on the corner of Commercial and India Streets, for 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 and the life story of George Cleeve, Portland’s lawsuit-happy co-founder.

The 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 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 comfortable cycling 8 to 10 miles on mostly flat terrain.

Please wear athletic clothing.


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