MA Inn to Inn Bike Tour – Great Freedom Adventures
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MA Inn to Inn Bike Tour

MA Inn to Inn Bike Tour

per person

Tour an area pivotal to US maritime history with natural harbors offering settlers protected waters from which to depart to the rich offshore fisheries.


Maritime New England Inn to Inn Bike Tour

Bike From Inn to Inn Discovering Maritime History Along the Massachusetts North Shore

New England Maritime History in the Country’s Oldest Seaports
Bike tour regions central to New England’s maritime heritage on Boston’s North Shore, Cape Ann and the Essex National Heritage Area. Bike from inn to inn exploring an area pivotal to US maritime history. Discover picturesque natural harbors that offered settlers protected waters from which to depart to the rich offshore fisheries. Visit some of the oldest towns in the US where fishing and boat building are still ways of life. View the beautifully maintained colonial homes and enjoy vibrant town centers. Visit historic areas that capture the essence of life in coastal colonial settlements, China Trade seaports and Witch Trial centers.

Classic Lighthouses, White-Sand Beaches and Rich Salt Marshes
Pedal landscapes and seascapes offering views of wildlife-filled salt marsh, lighthouses perched on rocky headlands and white-sand beaches backed by the sparkling Atlantic. The unique beauty of Boston’s North Shore has provided the backdrop for numerous movies. In fact, this remarkable region has a tremendous combination of cultural and natural diversity in a relatively small area that would be hard to match anywhere else.

Bike Stunning Routes From Inn to Inn
Great Freedom Adventures has crafted an exceptional inn to inn bike tour that showcases the area’s loveliest towns, historic sites, and natural beauty all linked together by wonderfully scenic cycling routes. Pedal rocky coastline where crashing waves infuse the air with the smell of salt and rugosa roses perfume tranquil coves with hidden beaches. Bike through the country’s first seaport and the oldest artist’s colony which remain as active today as they were centuries ago.

dsc_0076_000Walk, Kayak and Sail Too
Traverse a barrier island on boardwalks through an important wildlife habitat viewing marsh and maritime forests while listening to bird song. Walk trails through heather-covered dunes at Crane Wildlife Refuge. Kayak clear blue waters through estuaries of golden grasses and graceful shorebirds. Sail a harbor where reflections of fishing boats color the water and the setting sun colors the sky.

Savor Traditional New England Fare and Relax at Fine Inns
Sample the fresh lobster, succulent clams and the excellent variety of foods for which Boston’s North Shore is known. Rest at an oceanside grand hotel and lovely boutique inns. Enjoy dedicated service throughout this fascinating tour of Maritime New England.

Tour Highlights:

  • View quintessential New England villages, seacoast and farmland in one of the oldest established counties in the nation
  • Stay in Select Registry and boutique inns and a historic grand hotel
  • Enjoy a sunset sail on a graceful catamaran with on-board bar
  • Kayak the estuaries of the Essex River Basin to a secluded beach
  • Discover some of the most beautiful beaches on the Eastern Seaboard
  • Enjoy a classic Lobsta’ feast
  • Experience the tranquility of the “Great Marsh,” the largest continuous salt marsh north of Long Island Sound
  • Discover the sights, sounds and smells of a pristine coastal habitat of dunes, pine forests, cranberry bogs and salt marsh.
  • Spot some of the 350 species of resident and migratory birds in one of the nation’s finest bird watching areas
  • See the extraordinary collection of First Period homes in Ipswich, the largest concentration in the country
  • Tour the magnificent Crane Estate and explore the trails of Castle Hill by bike and foot
  • Learn about the legacy of the sea on maritime heritage scenic byways
  • Visit Salem, site of the infamous witch hunt of 1692. Explore the sites of your choice such as the Witch Museum, The Peabody Essex Museum, The House of the Seven Gables, unique shops
  • or the last complex of colonial era wharves in existence
  • Explore Gloucester of The Perfect Storm fame, the nation’s oldest seaport and glimpse everyday life in this authentic, working fishing community
  • Visit the country’s oldest artist colony and shop in galleries offering excellent local art
  • Experience the exquisite light at Rockport, a charming seaside community that attracts vacationers, artists, photographers and filmmakers from around the world

Note – This tour is also offered with a focus on the craft beer brewed in the region. Information can be found here: MA Bike & Beer Tour.

Tour Reviews & Testimonials

  • Include
    Bike Tour
  • Not Included
    Active Vacation
    Hiking Tour

Day 1

bike-hike-kayak-adventure-tripMeet in Ipswich in the early afternoon for a welcome lunch and bike fitting. Bike past salt-hay farms and seventeenth-century houses to Newburyport to explore this seaport’s wealth of history and charm. Walk lovely streets from the inn, past sidewalk cafés, unique shops and art galleries, to the riverfront boardwalk. Set sail by catamaran with on-board bar to watch the sunset. Enjoy dinner together at an excellent Newburyport restaurant. Biking Mileage: 13.4

Day 2

ma_itinerary_2Bike to Joppa Flats looking out for herons, egrets and possibly, a bald eagle.  Continue to Plum Island and the Parker River National Wildlife Refuge of over 4,600 acres of pristine and diverse coastal habitat. The 3,000 plus acres of salt marsh is one of the most productive ecosystems on the planet.  View the sanctuary from atop a fire tower then follow boardwalks from marshland to huge sand dunes to beachfront while watching for shorebirds and listening to songbirds. The cares of the world seem to wash away in this tranquil place. Bike to Plum Island Light at the confluence of river and ocean and stroll along the wide beach. Bike inland past old stonewalls and idyllic ponds, then return to Newburyport to explore more of the town's maritime history and wonderful shops. Enjoy a dinner of New England fare fresh from the ocean or farm. Biking Mileage: 18 or 32 with options for more

Day 3

ma_map_smBike through colonial towns and heritage farmland en route to Salem, a small city with a unique history as both a center of witch hysteria in 1692 and a major China trade seaport a century later. Explore this exciting place as you choose. Whether your interests are witch trials, colonial architecture, historic sights, museums, maritime history, art, antiques, shopping, or lazing on the beach, you will find it here. After, cycle to historic Ipswich, one of the oldest towns in America. Walk from the inn to enjoy dinner on your own at one of the excellent nearby restaurants, most offering locally brewed Ipswich Ale. Biking Mileage: 25, 30 or 48

Day 4

kayakers-resizedToday, cycle through gorgeous landscapes and seascapes that provided the backdrop for several movies and offer a real feast for the senses. View the shimmering greens, golds and blues along Plum Island Sound and Castle Hill, some of the most beautiful vistas on the northeast coast.  Explore a National Historic Landmark with its hilltop mansion, Italianate gardens, and manicured grounds with panoramic ocean views. Continue to a beach considered one of the most beautiful on the east coast, and an important nesting area for the threatened Piping Plover. Walk along the shore and hike trails through barrier island dunes and pitch pine forests. Next, explore this unique eco-system from the water on a kayak adventure, paddling bird-filled estuaries to a secluded beach.  Back in Ipswich, discover some of the architectural gems including numerous first period homes, visit the shops and galleries or just relax at the inn.  For dinner, enjoy a lobster bake prepared by our host with lobsters pulled fresh from his own traps. Bon Appetite! Biking Mileage: 20

Day 5

ma_itinerary_5Pedal the coast through quintessential New England coastal towns and visit beautiful Singing Beach to see if you can discover how it got its name. Cross the drawbridge to Gloucester and view the famous Fisherman’s Memorial. Explore this hardworking seaport and watch fishermen bringing in the catch. Gloucester’s working waterfront, the nation’s oldest, is still a highly productive fishing port. Visit the cafés and shops, then pedal out to a scenic and quaint neck of land to see America’s oldest art colony. Spin along dramatic rocky coastline perfumed by salt spray and roses with views of lighthouses and wide beaches along the way. Arrive in enchanting Rockport, a place known for luminous light and a picturesque harbor that attracts artists, photographers and filmmakers from around the world. Explore this charming town, then head to our luxurious waterfront inn to relax in the oceanview pool or on the wide veranda. Tonight, enjoy dinner in Rockport. Biking Mileage: 38

Day 6

father-son-resizedContinue to loop around Cape Ann visiting a quaint hamlet where life follows the tides as it has for centuries. A visit to the North Shore would not be complete without sampling the succulent fried clams for which this region is famous. Stop at a clam shack, one considered “an American cult classic,” to sample the clams and much more. If you like, visit the intriguing Essex Shipbuilding Museum or some of the shops in this antiquing mecca. Bike back to Ipswich by early afternoon to complete this exploration of New England's maritime heritage, natural beauty, rich culture and great biking. Biking Mileage: 26   Please Contact Us for detailed itinerary and arrival and departure information.

garrison-innGarrison Inn, Newburyport, MA - 2 NightsOur luxurious and elegant boutique hotel is also a National Historic Landmark. The inn is centrally located in the heart of the historic district, steps to fine shops, galleries, restaurants and the waterfront boardwalk. Treat yourself at the Spa Paradiso or enjoy the new pool and fitness center. Enjoy innovative breakfasts served in espresso bar fashion.

ipswich-innIpswich Inn, Ipswich, MA - 2 NightsOur host and hostess exude warmth and hospitality and the beautiful rooms in this Victorian home are sure to sooth. Delicious breakfasts are served in the light-filled dining room. Walk to all the sights and shops in Ipswich.
The Emerson Inn, Rockport, MA - 1 NightWe spend our last night in a historic grand hotel in which Ralph Waldo Emerson once laid his head. This Select Registry inn has stunning ocean views which you can enjoy from the pool, from your room or from a rocker on the veranda. Enjoy breakfast in the Grand Café overlooking the water.

2022 Dates

June 5-10  |  September 4-9

2022 Prices (Good till 11/15/21)

$3,195 per person, based on double occupancy. Single Supplement: $950.

Trip Length

6 days, 5 nights


Ipswich, MA

Cycling Level

Easy to Moderate

Daily Mileage



Relatively flat with occasional short hills.

Bikes: You may bring your own bike or use one of ours. 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:
  • 6 days of bicycling
  • Bicycle and helmet rental
  • 5 nights lodging
  • All breakfasts
  • 1 lunch and welcome reception
  • 4 dinners
  • Sunset sail
  • Kayak tour
  • Walks at various reservations and estates
  • 2 dedicated guides
  • Van support (for you and your treasures found along the way too)
  • Daily snacks and cold drinks
  • Maps and cue sheets for each day's ride
  • Luggage transport
  • Admission to:
    • Crane Estate
    • Crane Beach
    • Parker River National Wildlife Refuge
  • Tax and gratuity for meals and side excursions
  • Transport from/to the Ipswich train station or Peabody Logan Airport Express bus stop
  • Use of featherweight, high visibility, reflective mesh vest
  • Water bottle
Frequent Adventurers, GFA alumni, may deduct 5% from the tour price. Please contact us for youth and group rates. Custom dates and duration are available for groups of six or more. Please Contact Us for detailed itinerary and arrival and departure information.

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