Kennebunkport to Freeport Cycling Tour

Booking Form
Contact Us
Full Name*
Email Address*
Number of People*
Your Inquiry*
* I agree with Terms of Service and Privacy Statement.
Please agree to all the terms and conditions before proceeding to the next step

Book Now

Save To Wish List

Adding item to wishlist requires an account

  • 5 Days
  • 2024 DatesThis tour starts any Sunday or Monday between May - Oct
  • Difficulty LevelEasy - Sounds Like Fun

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 a GPS 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.)

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)


  • Discover Portland and Kennebunk
  • Enjoy a scenic ferry ride
  • Cycle past beaches and lighthouses

Pick Up/Drop Off


2024 Dates

Self-Guided Tours can start on any Sunday or Monday


Pricing:  $1795.00 per person

E-Bike: $250.00


Day 1Welcome 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 take time to discover Kennebunkport on your own.

Day 2To the Beach

Leaving Kennebunkport, you will pedal past charming houses on your way to East Coast Greenway, the Maine to Florida bike trail. 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 local call it, is an unpretentious beach town with an amusement park and pier.

Day 3The Lighthouse Ride

You begin your day riding a trail through the Scarborough Marsh. Leaving the marsh, you will pedal to Two Lights to and 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 and pedaling into Portland

Day 4To 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 areas 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.

Day 5 Return to Kennebunkport

One of our staff will pick you up after breakfast and shuttle you back to Kennebunkport or Portland.

Meals: Breakfast


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


Related Tours


Cycle the Maine Coast

16 Days
Love to bike? Then cycle the Maine Coast is the tour for you. Cycle the Maine Coast offers fourteen days of inn-to-inn cycling along the Maine Coast. Your […]
Pedal the Coast

Discover Penobscot Bay Multi-Sport

5 Days
Penobscot Bay is one of the richest fishing grounds in the world, producing more of the famous Maine Lobster than any other body of water. During your six-day […]
Pedal the Coast Light

Pedal the Coast Self-Guided

7 Days
This tour is the perfect opportunity to embark on an inn-to-inn bicycle tour, in a leisurely pace for those who wish to absorb the scenic beauty truly.