You can keep your car ferries and Segways — for my money, one of the best ways to tour the Calendar Islands is by bike.

Casco Bay is dotted with hundreds of islands. So many, in fact, that an English engineer quipped in the 1700s that there were “as many islands as there are days in the year.” The number has since been revised down from 365 to a bit less than 200, a nevertheless impressive number.

As we head into fall, we’re hitting that magic period between summer crowds and winter cold. In September and October, the roads on the islands offer a perfect combination of scenic views, warm temperatures and low traffic. Only a few miles from Portland, it’s easy to feel like you’ve discovered your own private island as you cruise around on two wheels.

The relatively flat terrain and small size of the islands — the largest, Chebeague, is just 3.2 square miles — means that even novice cyclists can tour the bay. Occasional rough patches and dirt roads make a hybrid or mountain bike advisable, but the grades are slight enough that you won’t even need a cycle with multiple gears.

At only a 15-minute ferry ride from Portland (with more than a dozen Casco Bay Lines departures a day), Peaks Island is undoubtedly the easiest island to reach.

The second-largest island in Casco Bay, 720-acre Peaks is home to roughly 1,000 year-round residents — a number that swells significantly in summer. The island offers a perfect mix of beauty and convenience for cyclists, with a town on the west side and unobstructed ocean views on the east.

The Peaks Island Loop, part of the Portland Trails network, is a 4-mile trek along the paved roads that circle the island. Starting with a right turn up the hill from the island’s ferry terminal, the route follows Island and Seashore avenues.

After half a mile, you leave the “urban” (using the term very loosely) part of Peaks at Woodlanding Cove, and follow the rocky shore and beaches looking out to the Atlantic. The road sticks to the coast for about two miles, and a short hill by Elm Tree Cove is followed by a left turn steering back through town.

No bike? No worries. Peaks is also home to Brad & Wyatt’s Bike Shop, where you can pick up a bike for just $5 an hour. The honor system box at the shop is a sign of Brad’s and Wyatt’s good natures — if no one is there to help you out, stuff your payment in the box and grab a bike. Also available at the shop are maps that offer a few more routes than the Island Loop.

A trip to Crown Pilot-lovin’ Chebeague can be short or long, depending on your approach. A ferry ride from Portland with Casco Bay Lines takes about an hour and a half, and drops you at a ferry terminal on Chebeague’s south end. The more expensive Chebeague Transportation ferry departs from Yarmouth, but deposits you on the island’s north end after only 15 minutes.

Your point of contact with Chebeague doesn’t really matter, because your plan of attack is about the same either way. A loop around the island is made by the appropriately named North and South roads. Riding this loop is about a 6-mile round trip when you include the spur to and from either ferry terminal.

Your trip will be made slightly longer, however, by the many dirt roads leading to the island’s shore.

The loop is pleasant, but restricts you largely to the interior of the island. To reach the myriad public beaches, you must explore the paths that lead off the paved road every few hundred yards.

My favorites? The beach at Indian Point on Chebeague’s southwest tip, which has surprisingly blue waters and high dune grass for a beach in Maine.

There are plenty of trails on the mainland, but if you’re looking for some great biking, I suggest heading out to sea. 

Josh Christie is a freelance writer and lifetime outdoors enthusiast. He shares this column space with his father, John Christie. Josh can be reached at:

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