Beaches and Backroads


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  • 3 Days
  • 2023 DatesJuly-Oct
  • Difficulty LevelEasy - Sounds Like Fun

Tour Overview

History buffs – salty dogs – those who cycle for the scenery … this weekend cycling tour is for you.  The seaside towns of Kennebunkport, Kennebunk, Arundel, and Cape Porpoise – collectively known as The Kennebunks – are saturated in maritime history, from times of salty sea captains, to a thriving ship building industry during which time as many as 100 ships were built and floated down the river a year, to the fisherman who for centuries have made a living off the coast’s rich marine resources.  Today, the stately homes of the sea captains are welcoming B&Bs; boat building is still present, including a boat building school just four miles from town; and many a local make their living on the sea as lobstermen and fishermen.

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
  • Expenses paid to sail on the Schooner and for the ferry transit
  • Experienced Summer Feet Guides
  • Detailed route notes and maps
  • 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

Pick Up/Drop Off

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


  • 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

2023 Dates

August 25-27
September 8-10
October 13-15


Beaches and Backroads $1595.00 per person
Bike Rentals: Hybrid Bike Rental: Included
Road Bike Rental: $150.00
E-Bike Rental: $150.00
Lodging Extras: Single Supplement: $400.00


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!

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, taking time to stop 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 along the way.  Once back on the roads, it’s time to saunter 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


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