Kennebunkport to Freeport Cycling Tour

A Self-Guided Kennebunkport to Freeport Bike Adventure

Embark on a delightful biking adventure from Kennebunkport to Freeport, where sandy beaches, bustling lobster boats, and vibrant communities create the perfect backdrop for your journey. Our five-day self-guided cycling tour offers an unparalleled opportunity to explore Maine’s iconic summer communities and its most lively city, each teeming with unique allure and charm.

We streamline your adventure by arranging comfortable lodging and taking care of your luggage transportation. You will be provided with Ride with GPS routes and detailed notes to ensure you don’t miss any of the spectacular highlights. The beauty of this self-guided tour lies in its freedom – you have the liberty to cycle at your own rhythm, pausing as often as you desire to absorb breathtaking views or explore hidden corners.

As you pedal along the scenic routes, you’ll encounter picturesque lighthouses and inviting beaches. An enchanting ferry ride will whisk you off to a beautiful island, offering a refreshing change of pace. This self-guided cycling journey promises not only physical activity but also a rich visual feast of Maine’s most captivating sights, encapsulating the very best this stunning state has to offer.

(Still making up your mind about how to organize your Maine trip? Browse our entire range of Multi-Day Bike Trips in Maine.)

Highlights

Pricing

Pricing: $1795.00 per person

E-Bike: $250.00

2025 Dates

Self-Guided Tours can start on any Sunday or Monday

Pickup/Drop Off

Kennebunkport

Itinerary

DAY 1 Welcome to Kennebunkport

One of our staff will meet you in Kennebunkport to introduce you to your bikes and answer any questions. After the introduction, there is an optional warm-up ride, or you can explore Kennebunkport on your own.

Cycling: 14 miles
Lodging: The Colony Hotel

DAY 2 To the Beach

Leaving Kennebunkport, you will pedal past charming houses on your way to the East Coast Greenway, a multi-use trail stretching from Maine to Florida. Your ride will take you along the coast to the towns of Biddeford and Saco. After cycling through these historic mill towns, you will continue to Old Orchard Beach. OOB, as the locals call it, is an unpretentious beach town with an amusement park and pier. From here you will cycle through the Scarborough Marsh before pedaling to your inn overlooking the ocean.

Cycling: 30 miles
Meals: Breakfast
Lodging: The Black Point Inn

DAY 3 The Lighthouse Ride

Today is all about lighthouses. Leaving the inn, you pedal to Higgins Beach, Two Lights State Park, and then onto the famous Portland Head Light, the most photographed lighthouse in America. Next stop is the Spring Point Ledge Light before rounding out your lighthouse tour at Bug Light and then pedaling “across the bridge” into Portland.

Cycling: 28 miles
Meals: Breakfast
Lodging: The Portland Regency or a similar hotel

DAY 4 To Chebeague and Beyond

Your morning begins with a scenic ferry ride among the “Calendar Islands” of Casco Bay. Your destination is Chebeague, the largest of the area’s islands. Enjoy a leisurely ride around the island before lunch at the award-winning Chebeague Island Inn. After lunch, hop the Cousin’s Island ferry and cycle across the causeway and on to Freeport, your home for the night.

Cycling: 19 miles
Meals: Breakfast
Lodging: The Harraseeket Inn

DAY 5 Return to Kennebunkport

After breakfast at your inn, hop on your bike for one final spin through the rural landscape of Freeport and the neighboring town of Brunswick. There are many opportunities to lock up your bike and take a walk if you are so inclined. You will be greeted by a Summer Feet crew member at noon today – please plan your morning accordingly.

Cycling: 21 miles
Meals: Breakfast

Please Ask a Question or give us a call at 1.866-857-9544 if you have any questions.

What's Included

4 nights’ lodging
All lodging taxes and gratuities
4 breakfasts
Hybrid bike and helmet
Scenic ferry ride
Detailed route notes and maps and turn by turn navigation using the Ride with GPS app (no cellular data needed)

Emergency support
Summer Feet Souvenirs – a cycling water bottle and t-shirt (available in men’s and women’s fit)

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.

It was a rainy day for our ride, but Lauren and Edna made it enjoyable. They went out of their way to make sure we enjoyed our time and got to see all the lighthouses. We really enjoyed the lunch, and they did a great job of tailoring the experience to the group. I can not recommend this tour enough and would do it again in better weather.

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