Kennebunk to Freeport


Beaches, lobster boats, and lively communities await you on your Portland to Freeport biking adventure. Discover Maine’s iconic summer community and most vibrant city on this wonderful 5 day self-guided cycling adventure. We arrange lodging, move your luggage and give you a gps and detailed notes.  You are free to cycle at your own pace, stop as often as you want, linger over beautiful views on your self-guided cycling adventure. Along the way, you will see lighthouses, beaches, ride a ferry to a wonderful island and see the best of Maine.

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

Price $1595.00 pp




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 take time to discover Kennebunkport on your own.

Day 2 To 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 3 The 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 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 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 pack to Kennebunkport or Portland.

Meals: Breakfast

Browse Trips


  • 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)


Departures: Self-guided tours can start on any Sunday or Monday

Pricing:  $1595.00 per person

E-Bike $200.00


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Belated thanks for a great trip. We were very fortunate to see a slice of Maine and to have many great experiences to remember. It was great to be so well looked after, with first-class bikes and organisation.

Simon Calder