The Kennebunks: Beaches and Backroads

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  • 3 Days
  • 2024 DatesJuly-Oct
  • Difficulty LevelEasy - Sounds Like Fun

Explore The Kennebunks with Summer Feet Cycling

Whether you’re a passionate history enthusiast, an adventurous cyclist, or someone who simply enjoys the magic of scenic landscapes, this weekend cycling tour is designed with you in mind. Venture into the historic seaside towns of Kennebunkport, Kennebunk, Arundel, and Cape Porpoise – collectively recognized as The Kennebunks – and immerse yourself in their rich maritime past.

The Kennebunks’ captivating history spans epochs, from an era dominated by hardy sea captains to a thriving shipbuilding industry that once saw as many as 100 magnificent vessels constructed and launched annually into the river. These towns have also been home to generations of fishermen who have thrived on the bounty of the coast’s rich marine resources.

Today, the echoes of this vibrant past still reverberate throughout The Kennebunks. The grand residences once belonging to sea captains now serve as inviting bed-and-breakfast establishments, preserving the charm of bygone days. Shipbuilding continues to be an integral part of local life, with a specialized boat-building school just four miles from the town center. The sea’s bounty is still harvested today by local lobstermen and fishermen, maintaining the maritime tradition that has defined The Kennebunks for centuries.

Join us as we pedal through history and experience the timeless allure of these maritime towns.

If you have any questions, don’t hesitate to get in touch

What's Included

  • Two nights’ lodging
  • All lodging taxes and gratuities
  • Most meals – including dinner both evenings, lunch on Saturday, and breakfasts at the inn
  • All taxes and gratuities for these meals
  • Experienced Summer Feet Guides
  • Turn by turn directions using Ride with GPS
  • Van support including fresh water, ample snacks, and “relief rides”
  • Summer Feet Souvenirs – a cycling water bottle and t-shirt (available in men’s and women’s fit)
  • Alcoholic beverages are not included in the package price and are always at your discretion


  • Cruise Maine’s rocky coast from the comfort of your bike
  • Discover lively beach communities
  • Feast on lobster caught by one of Kennebunkport’s own lobstermen

Pick Up/Drop Off

Summer Feet guides will meet you at your inn in Kennebunkport.


October 18-20


Beaches and Backroads $1595.00 per person
Bike Rentals: Hybrid Bike Rental: Included
E-Bike Rental: $200.00
Lodging Extras: Single Supplement: $500.00

Kennebunks Cycling Tour Itinerary

Day 1Cruising the Coast

Why save the best for last?  This afternoon you’ll meander along some of Kennebunkport’s loveliest roads and shorelines.  We’ll start by going inland where we’ll be likely to see sheep and alpacas and even a llama grazing at the Ewe and I Farm.  If you stop, they’ll visit – they’re quite friendly animals.  We’ll take a short cut through the woods along the Gravelly Brook Road, home of the Kennebunkport Conservation Trust and some of the Trust’s many local trails.  About a mile further along the route, you’ll find yourself surrounded by salt marsh, marking your close proximity to the Atlantic Ocean.  Hang a left once you arrive in the quaint lobstering village of Cape Porpoise and you’ll see the same sight that made me first fall in love with Maine.  A quiet cove, beautiful homes, a safe harbor full of working lobster boats, and of course the magical  islands of Cape Porpoise Harbor and the Goat Island Lighthouse.  The view simply can’t get any better.  We’ll finish our afternoon jaunt as we pass Walker’s Point – home of George and Barbara Bush – and then hug the coast the entire way back into town. Tonight’s dinner?  Lobstah!

  •  14 miles
  • Meals: Dinner
  • The Colony Hotel

Day 2Let’s Cover Some Distance

Goose Rocks Beach, Fortunes Rocks, the craggy shore of Biddeford Pool and the East Point Sanctuary, Wood Island Light, Hills Beach – these are some of the places we can adventure to when we head northeast of Kennebunkport.  You may recognize a few roads in and out of town from yesterday’s ride, but most of the journey will be uncharted territory for our group.  We’ll take a well-deserved break once we get to Biddeford Pool – there are great trails to walk, with crashing waves right at your side.  Finding a perfect picnic spot is hardly a challenge and once you’ve had your fill it’ll be time to get back to town and our evening treat!  Ride your bike, or finish the route in the van – it’s your vacation, do what feels good.

  •  13 or 32 miles
  • Meals: Breakfast & Lunch & Dinner


Day 3Kennebunk and Its Beaches

After another impressive breakfast at our inn, we’ll once again hop onto our bikes and, this time, explore what is west of the Kennebunk River. We’ll follow the rural River Road north and west to the first place where we can cross the river, Durrell’s Bridge. From there, be prepared to have your cycling socks knocked off as we ride past some of Kennebunk’s stateliest homes, including the Wedding Cake House on your right. Continue through Kennebunk’s downtown, stopping for ice cream at The Daily Scoop – if that’s your flavor. Then it’s time to travel back towards the sea, this time along the Mousam River. If conditions allow, we’ll take the Kennebunk Bridal Path along the river’s edge, watching for marsh birds and forest creatures. Once back on the roads, it’s time to stroll along Kennebunk’s many beaches. Take your time, watch the surfers, watch the waves, get off your bike, and put your feet in the sand – so luxurious. Pass back to the “other side of the bridge” and take your time through Kennebunkport’s Dock Square and back to the inn.

  • Cycling Options: 15 miles
  • Meals: Breakfast

Have a question? Please Get in Touch


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