North Shore Port-to-Port Bike Tour

Experience an Ecletic New England on our North Shore Port to Port Bike Tour

Great Freedom Adventures is excited to bring you our North Shore Port to Port bike tour! The Massachusetts North Shore is a New England coastal region bustling with activity and holds many surprises for guests, all within an hour of Boston. Escape to historic Newburyport and Rockport, where Federal-style mansions that, now preserved, give these coastal cities their distinctive character. Meander through quaint towns that make up Cape Ann nestled in between. Guests relish this tour for the miles of beaches, glades, and estuaries. Guides will lead you on this terrain rich with New England history, natural beauty, extraordinary coastal views, and fresh local cuisine.

  • 5 Day Adventure
  • April 18th – 22nd – (SOLD OUT)
  • June 25th – 29th – (SOLD OUT)
  • September 16th – 20th – (SOLD OUT)
A cyclist riding along a marsh on a North Shore bike tour

Learn more about our North Shore Bike Tour

Great Freedom Adventures has been operating in New England for several years. We work hard to create unique and new trips to help cyclist tourists explore new places and bike rides. Our guides provide a seamless experience for your trips, being an excellent resource during your travels. On this North Shore bike tour, a focus on unique lodging is only matched by excellent cuisine you’ll indulge in on tour. A maritime way of travel will bring us from port to port as we continue on bike to explore the area. Speak with one of our knowledgable travel consultants to learn more about our North Shore bike tour, as well as other tours in the area. We hope to see them soon!


  • 5 days of bicycling
  • Bicycle and helmet rental
  • Lodging
  • All breakfasts
  • 1 Lunch
  • 2 Dinners
  • Daily hearty snacks and cold drinks
  • Crane Estate
  • Crane Beach
  • Parker River National Wildlife Refuge
  • Tax and gratuity for meals and side excursions
  • Walks at various reservations and estates
  • Guided historic tour
  • 2 dedicated guides
  • Van support
  • Featherweight, high visibility, reflective vest
  • Water bottle
  • Maps and cue sheets for each day’s ride
  • Luggage transport


Inclusions and Amenities

All Inclusions and amenities are subject to change, should we change our stay or dinner options, comparable options will be provided. 

Packing List

  • 2 pairs of bike shorts so you can alternate every day
  • 1 pair of quick dry pants for cycling
  • 2-3 pairs of biking socks + 1 pair of waterproof socks
  • Bike shoes
  • 2 quick dry cycling jerseys + one long-sleeved jersey if the weather is colder
  • Arm warmers, leg warmers
  • Rain gear, including a helmet cover, shoe covers, pants, and jacket
  • Cycling gloves
  • Sunglasses
  • Bandana

Rider Level


Lodging Options

Standard Room at Various Hotels and Inns

Max Occupancy: 2 Guests

Single supliment available

Throughout the tour, guests will stay in a selection of upscale Inns and Hotels along the way. As many are Historic Inns, rooms may vary in design, aesthetics, and layout. We’ve provided some sample images to give you a sense of what your accommodations may look like. Please note in the room selection process; we ask that you choose between a shared or double occupancy room and a private room for individual guests.



Meals Included

Private Rooms



Begin our journey in Newburyport with an early afternoon welcome lunch and bike fitting.



Van service back to Newburyport or train departing Rockport. 

Day 1:

Discover the town of Newburyport like never before and start off this fantastic tour with a short ride across the Merrimack River and into Salisbury Salt Marsh. On your return explore cafés, museums, shops, and art galleries. End your evening with a festive dinner together at an excellent Newburyport restaurant.

Biking Mileage: 8.6

Day 2:

Trek past Joppa Flats looking out for herons, egrets, and possibly a bald eagle and on to Plum Island and the Parker River National Wildlife Refuge. View the sanctuary from atop a fire tower, then follow boardwalks through marshland, dunes, and beachfront while watching for shorebirds and listening to songbirds. Bike to Plum Island Light at the confluence of river and ocean. Return to historic Newburyport to explore more of the town’s maritime past. End your day with local New England fare.

Biking Mileage: 25.8

Day 3:

Following breakfast, bike on through historic and colonial towns and heritage farmland. Pay a visit to the town of Ipswhich on your way back to the coast where you will tour the impressive Crane Estate on Castle Hill. Continue on through Manchester-by-the-Sea and pedal the coast through quintessential New England coastal towns, visit beautiful Singing Beach, and discover how it got its name. Cross the drawbridge to Gloucester’s famous Fisherman’s Memorial. Visit Gloucester’s working waterfront, the Nation’s oldest fishing port.

Biking Mileage: 42.5m or 54.1m

Day 4:

Today you explore the stunning town of Rockport. Starting the day off with a cyle out to Lobster Cove and returning back to the scenic Emerson by the sea for an afternoon on your own. Explore this exciting place as you choose: Colonial architecture, museums, shipping history, art, antiques, shopping, or simply relaxing by the pool. Enjoy dinner at one of the excellent nearby restaurants, most offering locally brewed Ale.

Mileage: 12.6m

Day 5:

This morning, hike out to Halibut Point State Park for a short but sweet recovery walk  then depart back to Newburyport.

Booking Information


7 days prior to the adventure departure.


A deposit is due upon booking – $750 per person for five to eight day tours and $500 per person for three to four day tours. Payments may be made by check or credit card. Our receipt of the deposit, registration form, and signed Release form will secure your reservation.

An invoice for the balance will be emailed and final payment is due no later than 30 days (exceptions made for last minute booking) before the tour departure date. Payment may be made by check or online with a credit card. If final payment is not received by the due date, Great Freedom Adventures reserves the right to cancel the reservation.


All cancellations must be submitted in writing; refunds will be based on the day we receive written notice. Please purchase trip cancellation/travel insurance because exceptions to our cancellation policy cannot be made for any reason, including personal emergencies, illness or injury, canceled or delayed flights or ground travel to the tour departure point, or weather. Refunds will not be made for a participant arriving late or departing early from a tour, or for a participant not using accommodations, meals, or other services offered as part of a tour.

Cancellation Fees Are as Follows (Per Person):

Cancel 30 days or less from booking date – No charge (Does not apply to custom or private tours or to US tours booked within 60 days of departure or overseas tours booked within 90 days of departure.)
91 or more days before trip – $150
61-90 days before trip – $750 or $500 (loss of deposit)
31-60 days before trip – 50% of trip price
30 or less days before trip – 100% of trip price (20% of your payment may be applied to another of our tours departing within one year of original tour start date.)


Travel insurance is available from a number of insurers or their representatives, such as CSA Travel Protection or Travel Guard. You may compare prices and policies at Insure My Trip. We do not sell insurance or recommend any particular insurer or policy, but we highly recommend that you obtain travel insurance.