Around the Portland Peninsula Bike Tour

See the Real Portland—Neighborhoods, Harbors, and Hidden Views Locals Love

Portland’s peninsula isn’t big — but it is full of surprises. Quaint neighborhoods, historic homes, quiet waterfront paths, and scenic views that even longtime locals love to show off. On this 2.5-hour guided bike tour, you’ll experience Portland’s shape, soul, and stories the way people who live here do: on two wheels, with curiosity and a sense of joy.

This isn’t just a bike ride — it’s a shortcut into Portland’s heartbeat. You’ll glide along quiet ocean paths, climb gentle streets lined with Victorian houses, and weave through neighborhoods where every corner has a tale worth hearing. By the time you reach the cobblestones of the Old Port, you won’t just have seen Portland… you’ll feel it

If you have any questions about this tour, please talk with a local — we’re happy to help Looking for a longer cycling experience in Maine? Explore our Multi-Day Bike Tours in Maine.

Highlights

Ride along the Eastern Promenade-For peaceful water views
Explore Back Cove and its waterside trail
Learn Portland’s Colorful History
Visit Some of the Local’s Favorite Spots
Pedal through the historic West End

Pricing

Tour Price: $85 per person

E-Bike: $50

2026 Dates

Daily from May through October at 10:30 am or 2pm

Pickup/Drop Off

Tours depart at 10:30am or 2pm from the Portland Encyclepedia (located on the corner of Commercial and India Streets) and return usually 2.5 hours later.

Portland Peninsula Itinerary

Daily Tour

Your guide will greet you at The Portland Encyclepedia for bike and helmet fitting before leading you into the low-stress rhythm of the ride.

You’ll begin with a relaxed pedal on the Eastern Promenade Trail, where Casco Bay views stretch along the water and the city’s seafaring roots come alive.

From there, glide around Back Cove, where the skyline reflects on calm waters and old neighborhoods show their quieter side.

Next up is the West End — tree-lined streets, stately homes, and hidden architectural gems that tell the story of Portland’s growth through the years.

Finally, roll into the iconic Old Port, where historic brick, bustling shops, and local favorites welcome you to linger or continue exploring on your own.

Consider upgrading to a pedal-assist e-bike for added ease and confidence on the ride.

If you are looking to enhance your experience, consider upgrading to a Pedal-Assist E-Bike.

Participants must be 12 or older (16 to ride an e-bike) and comfortable cycling 8 to 10 miles on mostly flat terrain.

Tours run daily and often fill quickly in peak season.
Join us for a ride around Portland and see the city the way locals do.

Have a question or want to be sure this ride is right for you?
Talk with a local — we’re happy to help.

What's Included

Professionally fitted bike and helmet
Experienced, local guide(s)
Rear Bike Bag to hold your extra layer, water bottle, and essentials
Scenic routes and hidden views

We biked in October. Weather was pleasant. We used standard bikes. My wife and I are in our 50’s. We had an exceptional guide. We were able to see most of Portland in about 2.5 hrs. About 10 miles total.

I booked the Around the Peninsula tour for a large group of friends. I was nervous that 2.5 hours would be too strenuous, but the tour was awesome!!! Chuck and Molly are so fun and fantastic. The tour was perfectly paced, and I think it was a great way to see all of Portland. Highly recommend!!

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

Views were amazing. Guides were friendly and personable. Lobster roll was delicious. I upgraded to the ebike (first time riding one) and 10/10 recommend it. I wasn’t looking for a workout. Just wanted to see the sights and enjoy myself. Portland was my favorite stop from a New England cruise.

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.

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