Self-Guided Bike Tour of the New England Seacoast – With Guided Option – Great Freedom Adventures
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Self-Guided Bike Tour of the New England Seacoast – With Guided Option

Self-Guided Bike Tour of the New England Seacoast – With Guided Option

per person

Mass to Maine: Bike Tour Self-Guided Along Stunning Massachusetts, New Hampshire and Maine Coastlines

overlooking bay on self guided bike tourThe beauty of the New England coastline is world-renowned. Many have toured and biked portions of the coast. But few have biked 460 miles along the coasts of three states from Boston’s North Shore all the way to Bar Harbor, Maine.

Over the course of nine days, discover the varied scenes of the northern New England coast, from quiet cove beaches with gently lapping waves to rugged cliffs with thundering surf. Choose your dates and preferred bike touring style, then set out on this unforgettable journey. Bike tour self-guided and self-contained, self-guided with luggage transport and vehicle support, or fully guided and supported.

Embark from Massachusetts’ Cape Ann, in a historic town with the oldest working seaport in the US. From there, head north, crossing into New Hampshire and then into Maine. Along the way discover lively towns, quaint fishing villages, vibrant waterfronts, boat-filled harbors, picture-perfect lighthouses, wildlife filled estuaries, white-sand beaches, serene salt-marsh, old stone walls, small farms and the sparkling Atlantic guiding you north.

Acadia National Park, the tour’s destination, is a stunning place where the mountains meet the sea. Discover soaring granite cliffs, glacier carved lakes, wildflower-filled meadows and forested islands scattered in the sparkling azure waters.

All along the ride, clam shacks, cool cafés, lobster pounds, bakeries and eateries of all kinds wait to tempt and satisfy. If you are looking for the best lobster rolls around, the northern New England coast is where you’ll find them.

self guided bike tour Great Freedom AdventuresThroughout the journey, talk with friendly Yankees who offer a glimpse into a life spent fishing, boating, farming, painting, photographing or the myriad other professions of coastal residents. In the same café you’d be just as likely to speak with a neuroscientist developing a new treatment for a rare disease as a third generation lobsterman or woman developing creative new fishing practices to ensure the industry’s sustainability.

An adventure this awe-inspiring deserves an equally inspirational finale – and it delivers! Cap off the pilgrimage with an event that serves as a rite of passage for many. Climb to the summit of Cadillac Mountain in Maine’s Acadia National Park to be among the first in the US to watch the sun make its magnificent appearance above the horizon. The sun’s rays bathe island-dappled Frenchman’s Bay, the park and much of Maine beyond in golden light. It’s a moving experience that will stay with you always.

Tour Highlights:

  • Bike tour self-guided or guided through diverse coastal and inland terrain
  • View the iconic Fisherman’s Memorial
  • See where the Andrea Gail of Perfect Storm fame embarked
  • See shipbuilding and maritime museums
  • Visit Strawbery Banke living history museum
  • Cycle through wildlife refuges
  • Stop in Portland and eat at one of the city’s many excellent restaurants
  • See several iconic lighthouses
  • View the colonial architecture of some of the oldest homes in the US
  • Discover small craft beer breweries
  • Explore Mount Desert Island & Acadia National Park
  • Bike the iconic Loop Road
  • Explore the streets, shops, galleries, restaurants and pubs in Bar Harbor
  • Bike to the summit of Cadillac Mountain and watch the sunrise!

    Day 1

    self guided bike tour day 1Meet in Gloucester, MA a historic coastal city on Cape Ann north of Boston. Gloucester is home to America’s oldest seaport and the oldest working art colony in North America. For over 400 years, Gloucester’s rugged coastline, scenic coves, beautiful beaches and safe harbors have drawn fishermen, artists and visitors. View the iconic Fisherman’s Memorial, a moving tribute to those lost at sea. Watch the drawbridge open for passing vessels. Bike to Rocky Neck and the numerous artist galleries. Perhaps enjoy a beer at Cape Ann Brewing Co followed by dinner at one of Gloucester’s excellent restaurants. Enjoy sensational seaside views at the waterfront lodging. Biking Mileage: ~ 7

    Day 2

     new england self guided bike tour day 2Cycle past coastal inlets, swaths of salt marsh, fishing towns, the shipbuilding museum in Essex and through farmland consisting of heritage farms and salt-hay farms. Take time to refuel in the lively and handsome colonial town of Newburyport before continuing over the Merrimack River and into New Hampshire. Follow the NH coastline to arrive in Portsmouth, a bustling and charming seaport city, named “One of America’s prettiest towns” by Forbes Magazine. View 17th and 18th century homes, and walk to Strawbery Banke an outdoor living history museum. Stay in the heart of Portsmouth, walking distance to restaurants, shops and sites. Biking Mileage: ~ 57

    Day 3

    new england self guided bike tour day 3Cross the Piscatuqua River to enter Maine and bike through the picturesque coastal villages of southern Maine. Circumnavigate Cape Neddick viewing the oft-photographed Nubble Lighthouse. Pedal past the tidal estuaries of a national estuarine research reserve and a national wildlife refuge, arriving at the charming town of Kennebunkport. Discover a fishing village that was the site of the original English settlement in Kennebunkport. The night’s destination is a popular summer resort town where you can relax on the beach and swim in the ocean from your beachfront accommodations. Biking Mileage: ~ 60

    Day 4

    self guided bike tour Great Freedom Adventures day 4Continue cycling the coastline and inland farms, bike the perimeter of Cape Elizabeth and view the Portland Head Light, Maine’s oldest working lighthouse and one of the most photographed on the east coast. Enter Portland, Maine’s largest city. The Old Port section features working fishing wharves and shops while the waterfront promenade offers beautiful views of Casco Bay and the mountains. Refuel at one of the many fine cafes or restaurants for which Portland is known. Continue north finishing the day in a small city known for shipbuilding and a rich maritime heritage. Biking Mileage: ~ 68

    Day 5

    new england self guided bike tour day 5Continue along the coast passing picturesque harbors studded with lobster boats and sailing vessels. Stop in lovely seaside towns offering cozy cafes and unique shops. Discover scenic peninsulas cycling past fields of blue lupines and white daises ending at the sparkling blue Atlantic. Grab a bite in charming Rockland, known for its concentration of excellent local art and art museums. See Rockport, a scenic gem on a picture-perfect harbor and continue to Camden, the day’s destination. Set on Penobscot Bay, Camden is often called the “Jewel of the Coast” and overlooks a boat-filled harbor and the Curtis Island Light. From your in-town lodging, walk the High Street Historic district and check out the fine shops. If time permits, take a short hike to a mountaintop offering sensational views of the harbor and the islands. Walk across the street from the inn to the brewpub or to one of the many excellent restaurants in town. Biking Mileage: ~ 73

    Day 6

    new england self guided bike tour day 6The journey continues while cycling past small rural farms and sleepy hamlets. Travel to the tip of a peninsula jutting into Penobscot Bay to the lovely town of Castine. This small town is one of the country’s oldest and is home to the Maine Maritime Academy. The idyllic main street is lined with historic homes while handsome, turn-of-the-century estates command stunning views at water’s edge. Biking Mileage: ~ 55

    Day 7

    new england self guided bike tour day 7Bike the perimeter of a peninsula with some of the most quintessential of Maine fishing villages and spectacular coastal views. Cross a bridge where local daredevils jump to ride the rapids when the rushing tide comes in. Continue on to finish in Bar Harbor, a beautiful town with a deep-water port that is something of a throwback to its 19th century roots as a vacation spot for the upper crust. Today, Bar Harbor remains a fabulous vacation destination offering outdoor activities of all kinds, great restaurants, lobster shacks, brewpubs and wonderful shops. Bar Harbor, Mt Desert Island and Acadia National Park comprise the number one tourist destination in Maine and for good reason. With forested hills, glacier-formed lakes, rocky beaches, ocean cliffs and panoramic mountaintop views, the region is exceptionally beautiful. Biking Mileage: ~ 79

    Day 8

    new england self guided bike tour day 8Bike the iconic Loop Road in the park and carriage roads as desired and discover the remarkably unspoiled beauty of Acadia National Park and Mt Desert Island. Explore rocky headlands, sparkling lakes, lush forests and picturesque fishing villages. Biking Mileage: ~ 45

    Day 9

    new england self guided bike tour day 9Finish this epic MA to ME trek with an optional early morning, 3.2-mile climb up fabled Cadillac Mountain. With grades ranging from 4.9 to 9.6%, completion of the challenging climb warrants major bragging rights. If the climb isn’t breathtaking enough, the sensational summit views of Frenchman’s Bay, Bar Harbor, and the Cranberry and Porcupine Islands surely are. For much of the year, Cadillac Mountain is the first place in the US to see the sunrise. Standing atop the summit and watching the sun rise above the horizon, bathing the landscapes and seascapes in a golden glow, is truly magical and deeply inspiring. It’s an unforgettable experience to cap off an unforgettable cycling adventure. Biking Mileage: ~ 14

    Please contact us for details about the accommodations.


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    Trip Length

    9 days, 8 nights


    Gloucester, MA/Bar Harbor, ME

    Daily Mileage

    Biking: 7-79

    Total Mileage

    About 460

    Cycling Level



    Predominantly flat with hills in some sections


    You may bring your own bike or use one of ours on partially or fully guided options. GFA bikes are high quality, lightweight, available with either drop or straight handlebars and are equipped with computer, mirror, waterbottle, handlebar bag, map case and seat pack with essentials.

    What’s Included: Please contact us for more details about what’s included in each touring option: fully self-guided, self-guided with vehicle support and fully guided and supported.
    • 8 nights lodging
    • 5 breakfasts
    • Maps/cue sheets/GPS routes
    • Information about the areas, local sites and suggestions for dining options
    • Add the following for partially and fully guided options:
      • Bicycle and helmet rental if needed
      • Daily snacks and drinks
      • Transport from/to train stations
      • Luggage transport
      • Vehicle & mechanical support
      • Waterbottle
      • Add the following for fully guided option:
        • Second guide to cycle with guests
        • On-route sharing of area information
    Frequent Adventurers, GFA alumni, may deduct 5% from the tour price. Please Contact Us for detailed itinerary and arrival and departure information.

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