With almost 400 miles from Kittery to the Canadian border, the coast of Maine presents incredibly diverse landscapes brimming with New England charm. This trip encompasses the very best that coastal Maine has to offer, from quaint artistic towns to the dramatic beauty of craggy shorelines that look out to historic island lighthouses.
Treat yourself to a variety of Maine delicacies like smoked salmon, fresh blueberries, the local favourite ‘whoopee pie’ and the world-famous Maine lobster. This distinctive trip gives you a unique insight into the creativity and beauty of the area as you ride through Acadia National Park, along the Schoodic Peninsula and through picturesque waterfront towns, all the while spoilt with unmatched ocean views.
Undoubtedly a highlight of your trip, the accommodation featured on this holiday is of great standard. You’ll spend your week in charming New England Inns dotted along Maine’s rugged coastline, with the exception of your first night in Portland city. Brimming with tradition and warm hospitality, a cosy room and hearty breakfast awaits you after an exhilarating day cycling.
Add extra nights in Portland or Boston should you want to explore these exciting American cities.
Key Information
Trip Code
C07MN
Ways to Travel
Self-Guided Holidays
Countries
USA
What's Included
7 nights in traditional New England Inn's
All breakfasts
Management by your local Headwater-appointed agent
Headwater navigation app
High quality bikes
Luggage transfers between hotels
All lodging taxes and gratuities
Transfer between Portland & your first/last inns and car transfers as per itinerary
Round trip ferry between Bar Harbour and Winter Harbour
7 days of Cycling
Day 2
39 km / 24.2 miles
Day 3
43 km / 26.7 miles
Day 4
36 km / 22.4 miles
Day 5
17 km / 10.6 miles
Day 6
43 km / 26.7 miles
Day 7
49 km / 30.4 miles
Day 8
36 km / 22.4 miles
Highlights
Step back in time to a simpler way of life in the tranquil seaside retreat of Maine
Luminous lighthouses, luxurious lobsters, and lush scenic trails await
Spend your nights at quaint New England Inns with devoted hospitality
Itinerary
First Destination:
Portland
Next Destination:
Portland
Meals included:None
Meals included:Breakfast
Meals included:Breakfast
Meals included:Breakfast
Meals included:Breakfast
Meals included:Breakfast
Meals included:Breakfast
Meals included:Breakfast
First Destination:
Portland
Next Destination:
Portland
After arriving in Boston, you’ll take a local bus to Portland, Maine where your hotelier will pick you up. You’ll spend your first night in Portland to rest up before being collected the following morning for your transfer to Spruce Head.
Overnight Portland Regency Hotel & Spa, Portland.
You’ll be met at your Portland hotel and transferred to your first traditional New England Inn located in Spruce Head. From here, you’ll embark on your first ride along coastal roads to the fishing village of Port Clyde and onto Marshall Point lighthouse, made famous by Forrest Gump. In the evening, you’ll have plenty of time to marvel at the coastal views from the lovely garden of your inn.
Overnight Craignair Inn, Spruce Head.
Meals included:Breakfast
Take a moment to enjoy your morning coffee overlooking the beautiful ocean before setting off to Birch Point State Park, home to the fascinating Owls Head lighthouse standing guard over Penobscot Bay. Continue to the eclectic village of Rockland, known as one of the world’s largest distributors of lobster. You have the option to visit Farnsworth Museum of Art featuring an extensive collection of art from the Wyeth family. Rockland is also home to many charming shops and galleries so there’s plenty to explore at your own pace this evening.
Overnight Berry Manor Inn, Rockland.
Meals included:Breakfast
You will enjoy great views of the Camden Hills and Rockland Harbour as you take an early morning ferry to Vinalhaven. Spend the day discovering the island, browsing downtown, and cycling up the island. Enjoy a swim in an old granite quarry and get a glimpse into island life before returning on the ferry back to Rockland.
Overnight Berry Manor Inn, Rockland.
Meals included:Breakfast
Today, you have some lovely options to consider for your ride. As the route from Rockland to Camden is 16km, we have a couple of loop rides that you can add in at Beauchamp Point (this is a beautiful 11km coastal ride through a natural reserve) and in the Camden Hills state park where sweeping views of Camden and Penobscot Bay await (24km). On your arrival in Camden, take your time wandering around this picturesque town, featuring a well-sheltered harbour surrounded by lush forests and hills.
Overnight Blue Harbor House, Camden.
Meals included:Breakfast
Your morning begins with an included transfer to Bar Harbour, the gateway to Acadia National Park. This stunning national treasure will be your home for the day as you ride through breath-taking scenery along Acadia’s famous carriage roads. Gifted by philanthropist John D. Rockefeller Jr, he envisioned motor-free byways to visit the heart of Mount Desert Island taking advantage of the incredible scenic views; thus, the carriage ways were created. This is a fantastic ride where you become fully immersed in the best of Maine’s captivating landscapes.
Overnight Sandbar Cottage, Bar Harbour
Meals included:Breakfast
A highlight of your week, your day begins with a unique ferry ride across Frenchman Bay to Winter Harbour and the Schoodic Peninsula. With over 27 acres of unique pink granite shores, it’s easy to see why artists are frequently inspired by this stunning peninsula. Along your ride, you’ll be rewarded with remarkable views over Mount Desert Island, Cadillac Mountain, and the historical lighthouses of Mark Island, Baker Island, and Egg Rock. Admire the dramatic waves as they crash into Schoodic’s rugged shore before continuing to a traditional lobstering community.
Please note, if you have opted for an e-bike on this trip, the ferry does not accept e-bikes therefore an alternative route is available on the quieter side of Acadia in Southwest Harbour (58km).
Overnight Sandbar Cottage, Bar Harbour.
Meals included:Breakfast
What better way to end your New England escape than to cycle Acadia National Park’s famous Park Loop, winding along the craggy shore. You have the option to climb Cadillac Mountain, the highest point on the North Atlantic seaboard as a spectacular finish to your week!
Transfer at noon back to Portland for your return bus to Boston Airport or for an extra night or two in this bustling American city.
Meals included:Breakfast
Dates & Prices
Skip the hassle: We’ll handle your trip from start to finish, with competitive flight prices, dates that suit you, 24-hour support, loyalty discounts, and peace of mind for delays or disruption.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5000 (excl. flights)
Saturday 16 May 2026 to Saturday 23 May 2026
Saturdayto
Saturday
Availability
Guaranteed (On Request)
This departure is guaranteed to go ahead and can be booked, although some components will need to be requested. Please click Continue to proceed with booking or contact our Sales team for assistance.
This departure is guaranteed to go ahead and can be booked, although some components will need to be requested. Please click Continue to proceed with booking or contact our Sales team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5000 (excl. flights)
Saturday 23 May 2026 to Saturday 30 May 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5000 (excl. flights)
Saturday 30 May 2026 to Saturday 06 Jun 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5000 (excl. flights)
Saturday 06 Jun 2026 to Saturday 13 Jun 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Saturday 13 Jun 2026 to Saturday 20 Jun 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Saturday 20 Jun 2026 to Saturday 27 Jun 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 27 Jun 2026 to Saturday 04 Jul 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 04 Jul 2026 to Saturday 11 Jul 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 11 Jul 2026 to Saturday 18 Jul 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 18 Jul 2026 to Saturday 25 Jul 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 25 Jul 2026 to Saturday 01 Aug 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 01 Aug 2026 to Saturday 08 Aug 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 08 Aug 2026 to Saturday 15 Aug 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 15 Aug 2026 to Saturday 22 Aug 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 22 Aug 2026 to Saturday 29 Aug 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 29 Aug 2026 to Saturday 05 Sep 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 05 Sep 2026 to Saturday 12 Sep 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 12 Sep 2026 to Saturday 19 Sep 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 19 Sep 2026 to Saturday 26 Sep 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
Saturday 26 Sep 2026 to Saturday 03 Oct 2026
Saturdayto
Saturday
Availability
On Request
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
This trip is available on request. Please proceed with your booking online or contact our Sales Team for assistance.
Optional Single Supplement
+USD 1229 Available upon Request
USD 5180 (excl. flights)
Book with USD 1295 deposit
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Your Group, Your Adventure
Want to choose your travel companions? Gather your family and friends and let us create a Private Adventure just for you.
Your first night is spent in Portland Harbour Hotel, an elegant and historical building in the Old Port District of Portland. With a luxury spa and creative onsite restaurant, this is the perfect place to rest up before beginning your cycling tour.
Add extra nights in Portland if you’d like to explore this bustling city. There’s plenty to see from whale watching to the renowned Portland Symphony Orchestra!
Craignair Inn, Spruce Head
Perfectly nestled along the craggy coast, this quiet escape serves up classic hospitality for a unique and welcoming stay. Many of the rooms have terraces with ocean views to enjoy all evening. There’s also an excellent restaurant and bar offering a relaxed setting and high-quality, local food.
Berry Manor Inn, Rockland
Another beautiful inn located in the historic district of Rockland, Berry Manor Inn is a luxury coastal inn, in a beautiful Victorian home. Renowned for its homemade pies and grand hospitality, this elegant getaway allows guests access to a 24 hour pantry and a lovely garden to relax in.
Sandbar Cottage, Bar Harbour
Your final classic New England Inn is just steps from the waterfront in Bar Harbour where you’ll enjoy a boutique cottage experience. Relax in the lovely gardens on the terrace when you’re not enjoying the beautiful town of Bar Harbour.
Hearty breakfasts are provided at each inn and there are plenty of restaurant options within each town.
Essential Information
As a certified B Corp, we’re on a mission to improve our social and environmental impact across all our adventures.
This ‘nature positive’ approach is designed to help nature and communities thrive in harmony through practical solutions, such as reducing carbon and waste on our trips, supporting conservation projects through the Exodus Adventure Travels Foundation, and rewilding 100 square metres for every Exodus traveller.
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